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130-15-4

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130-15-4 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 130-15-4 differently. You can refer to the following data:
1. yellow to green powder
2. 1,4-Naphthoquinone is a yellow to greenishyellow crystalline solid. Pungent odor like benzoquinone.

Uses

Different sources of media describe the Uses of 130-15-4 differently. You can refer to the following data:
1. 1,4-Naphthoquinone is used as a strong dienophile in Diels-Alder reaction. It is also used as a precursor to anthroquinone and 5-nitro-1,4-naphthalenedione, which finds application in the preparation of aminoanthroquinone and is also used as a dye precursor. It is a basic component of Vitamin K.
2. antibacterial, antineoplastic

Synthesis Reference(s)

Synthesis, p. 330, 1977 DOI: 10.1055/s-1977-24385Tetrahedron Letters, 31, p. 4871, 1990 DOI: 10.1016/S0040-4039(00)97755-4

General Description

Yellow needles or brownish green powder with an odor of benzoquinone.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,4-Naphthoquinone may react with many acids and bases liberating heat and flammable gases (e.g., H2). The heat may be sufficient to start a fire in the unreacted portion of the ketone. May react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. May react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 1,4-Naphthoquinone emits toxic fumes and smoke.

Fire Hazard

Flash point data for 1,4-Naphthoquinone are not available; however, 1,4-Naphthoquinone is probably combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

1,4-Naphthoquinone is used as a polymerization regulator for rubber and polyester resins; in the synthesis of dyes and pharmaceuticals; and as a fungicide and algicide.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise the quinone from diethyl ether (charcoal). It distils in steam. It also crystallises from *benzene or aqueous EtOH and sublimes in a vacuum. [Beilstein 7 IV 2422.]

Incompatibilities

Ketones are incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrated amines, azo, diazo, azido compounds, carbamates, organic cyanates. May react with many acids and bases liberating heat and flammable gases (e.g., hydrogen) generating heat may be sufficient to start a fire in the unreacted portion of the ketone. May react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (e.g., hydrogen) and heat. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. May react violently with aldehydes.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 130-15-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 130-15:
(5*1)+(4*3)+(3*0)+(2*1)+(1*5)=24
24 % 10 = 4
So 130-15-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

130-15-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10958)  1,4-Naphthoquinone, 97+% (dry wt.), cont. up to 5% water   

  • 130-15-4

  • 100g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A10958)  1,4-Naphthoquinone, 97+% (dry wt.), cont. up to 5% water   

  • 130-15-4

  • 500g

  • 888.0CNY

  • Detail
  • Alfa Aesar

  • (A10958)  1,4-Naphthoquinone, 97+% (dry wt.), cont. up to 5% water   

  • 130-15-4

  • 2500g

  • 3568.0CNY

  • Detail

130-15-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-naphthoquinone

1.2 Other means of identification

Product number -
Other names 1,4-Naphthalenedione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Process regulators
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:130-15-4 SDS

130-15-4Synthetic route

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Heating;100%
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 1.5h;100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
naphthalene
91-20-3

naphthalene

A

phthalic anhydride
85-44-9

phthalic anhydride

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 100%
B 0.05%
With oxygen at 340 - 360℃;A 100%
B 0.1%
With oxygen at 340 - 360℃;A 100%
B 0.02%
α-naphthol
90-15-3

α-naphthol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With Co(salN-Medpt); oxygen In acetonitrile for 0.5h;100%
With C126H112O32S6; oxygen In toluene for 1.33333h; Irradiation;100%
With K10 montmorillonite; iodic acid for 0.333333h; Heating;97%
1,4-dimethoxynaphthalene
10075-62-4

1,4-dimethoxynaphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With silver(II) oxide; nitric acid In acetone at 20℃;100%
With N-Bromosuccinimide; sulfuric acid In tetrahydrofuran; water at 20℃; for 0.25h;98%
With manganese(IV) oxide; nitric acid In dichloromethane for 1.5h; Ambient temperature;95%
4-methoxynaphth-1-ol
84-85-5

4-methoxynaphth-1-ol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;100%
With silica gel supported cerium(IV) ammonium nitrate-NaBrO3 In dichloromethane; water at 40℃; for 2h;95%
With Pyridine-2,6-dicarboxylic acid N-oxide; tert.-butylhydroperoxide; ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 11h;91%
p-benzoquinone
106-51-4

p-benzoquinone

(E,E)-2-pyridyldimethyl(buta-1,3-dienyl)silane
270589-03-2

(E,E)-2-pyridyldimethyl(buta-1,3-dienyl)silane

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 38h;100%
With hydrogenchloride In water at 20℃; for 38h; Product distribution; Further Variations:; Reagents; Solvents; Diels-Alder reaction;100%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

phthalic anhydride
85-44-9

phthalic anhydride

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃;A 100%
B 0.01%
With oxygen at 340 - 360℃;A 100%
B 0.01%
With oxygen at 340 - 360℃;A 100%
B 0.01%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

C

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 0.01%
B 100%
C 0.02%
With oxygen at 340 - 360℃;A 0.03%
B 100%
C 0.05%
With oxygen at 340 - 360℃;A 0.01%
B 100%
C 0.01%
Reaxys ID: 11464679

Reaxys ID: 11464679

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

C

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 354 - 357℃;A 0.2%
B 100%
C 0.15%
1,4-diaminonaphthalene
2243-61-0

1,4-diaminonaphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With sodium periodate In water; ethyl acetate at 20℃; for 0.25h;98%
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.166667h;90%
4a,5,8,8a-tetrahydro-1,4-naphthoquinone
6271-40-5

4a,5,8,8a-tetrahydro-1,4-naphthoquinone

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With H7PMo8V4O40 at 70℃; for 1h;96%
2,3-epoxy-1,2β,3β,4-tetrahydronaphthalene-1,4-dione
15448-58-5

2,3-epoxy-1,2β,3β,4-tetrahydronaphthalene-1,4-dione

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With molybdenum hexacarbonyl In toluene for 7.5h; Heating;95%
4-amino-1-naphthol
2834-90-4

4-amino-1-naphthol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With sodium hypochlorite; Dowex 1X8-200 - chloride form In 1,2-dimethoxyethane for 1.41667h; Oxidation;93%
With Montmorillonite K10; iodic acid at 61℃; for 0.00555556h; microwave irradiation;88%
With potassium nitrate; trifluoroacetic acid at -20℃; for 0.583333h;75%
With chromium(III) oxide; sulfuric acid
4-bromo-1-naphthol
571-57-3

4-bromo-1-naphthol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;93%
1-naphthalenecarboxylic acid
86-55-5

1-naphthalenecarboxylic acid

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;92%
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 16h;89%
With cerium(IV) ammonium sulphate; sulfuric acid In acetonitrile at 25℃; for 2h;42%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 16h;91%
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;87%
With cerium(IV) ammonium sulphate; sulfuric acid In acetonitrile at 25℃; for 24h;50%
With dihydrogen peroxide; acetic acid auf dem Dampfbad;
C21H18ClNO3

C21H18ClNO3

4-(4-chlorophenyl)-3-methoxyazetidin-2-one

4-(4-chlorophenyl)-3-methoxyazetidin-2-one

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With ceric(IV) tetra-n-butylammonium nitrate; water In dichloromethane at 20℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature;A 91%
B n/a
naphthalene
91-20-3

naphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; [MnIV(N,N'-di-tert-butyl-2,11-diaza[3.3](2,6)-pyridinophane)(OH)2]2+; tert-butylammonium hexafluorophosphate(V) In 2,2,2-trifluoroethanol; acetone at -30℃; for 0.5h; Kinetics; Temperature; Solvent; Electrochemical reaction;90%
With ceric methanesulfonate In water; 1,2-dichloro-ethane at 60℃; for 0.583333h;89%
With perchloric acid; cerium(IV) perchlorate In tetrachloromethane; water; acetonitrile for 1.5h; Oxidation;85%
1-amino-naphthalene
134-32-7

1-amino-naphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With sodium hypochlorite; Dowex 1X8-200 - chloride form In 1,2-dimethoxyethane for 0.75h; Oxidation;90%
With Montmorillonite K10; iodic acid at 58℃; for 0.00555556h; microwave irradiation;72%
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 0℃;57%
2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

A

o-Nitrobenzenesulfonate
30904-41-7

o-Nitrobenzenesulfonate

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With potassium superoxide In acetonitrile at -35℃; for 6h;A n/a
B 85%
4-hydroxy-1-naphthaldehyde
7770-45-8

4-hydroxy-1-naphthaldehyde

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With potassium nitrososulfonate In chloroform for 9h; pH 6;84%
4-methoxymethoxy-1-naphthol

4-methoxymethoxy-1-naphthol

A

2,2'-binaphthoquinone
3408-13-7

2,2'-binaphthoquinone

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With silver(II) oxide; nitric acid In acetone at 20℃;A 83%
B 9%
5,8-dihydro-1,4-naphthalenediol
3090-45-7

5,8-dihydro-1,4-naphthalenediol

A

5,8-dihydronaphthalene-1,4-dione
6295-28-9

5,8-dihydronaphthalene-1,4-dione

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With H7PMo8V4O40 In chloroform at 70℃; for 1h; Product distribution; Further Variations:; Temperatures; Solvents; reaction times;A 6%
B 82%
methanol
67-56-1

methanol

N-(4-Methoxy-1-naphthyl)acetamide
51687-74-2

N-(4-Methoxy-1-naphthyl)acetamide

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; silica gel; triethylamine at 20℃; for 4h;82%
α-naphthol
90-15-3

α-naphthol

A

1,2-naphthoquinone
524-42-5

1,2-naphthoquinone

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With potassium peroxymonosulfate; sodium ortho-iodobenzenesulfonate; sodium sulfate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In ethyl acetate at 20℃; for 24h; regioselective reaction;A 78%
B 6%
With 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride In dichloromethane at -80℃;A 15%
B 20%
With 3,3-dimethyldioxirane In acetoneA 14%
B 17%
1-(trimethylsiloxy)-1,3-butadiene
63383-46-0

1-(trimethylsiloxy)-1,3-butadiene

1,4-benzoquinone-2-carboxylic acid
5794-62-7

1,4-benzoquinone-2-carboxylic acid

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
In dichloromethane for 16h; Ambient temperature;78%
4-methoxynaphth-1-ol
84-85-5

4-methoxynaphth-1-ol

A

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxone In water; acetonitrile at 20℃; for 16h;A 78%
B 12%
C29H21ClN2O4

C29H21ClN2O4

2-(2-(4-chlorophenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

2-(2-(4-chlorophenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With ceric(IV) tetra-n-butylammonium nitrate; water In dichloromethane at 20℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature;A 78%
B n/a
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

di-(p-methoxyphenyl)tellurium oxide
57857-70-2

di-(p-methoxyphenyl)tellurium oxide

A

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
In chloroformA n/a
B 76%
m-Anisidine
536-90-3

m-Anisidine

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-(3-methoxyphenylamino)naphthalene-1,4-dione
64505-63-1

2-(3-methoxyphenylamino)naphthalene-1,4-dione

Conditions
ConditionsYield
In ethanol at 20℃; Reagent/catalyst;100%
With copper(II) acetate monohydrate; acetic acid at 60 - 70℃; for 0.5h; Under air;93%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h;76%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With acetic acid; zinc Ambient temperature; sonication, less than 5 min;100%
With hydrogen; palladium 10% on activated carbon under 2585.81 Torr; for 6h;100%
With sodium dithionite In diethyl ether; water at 20℃; for 1h;100%
2,3-bis<(trimethyksilyl)methyl>-1,3-butadiene
82167-48-4

2,3-bis<(trimethyksilyl)methyl>-1,3-butadiene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2,3-Bis-trimethylsilanylmethyl-1,4,4a,9a-tetrahydro-anthraquinone
82167-50-8

2,3-Bis-trimethylsilanylmethyl-1,4,4a,9a-tetrahydro-anthraquinone

Conditions
ConditionsYield
With hydroquinone In toluene Heating;100%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-chloro-1,4-naphthoquinone
1010-60-2

2-chloro-1,4-naphthoquinone

Conditions
ConditionsYield
With chlorine; mercury(II) oxide In tetrachloromethane for 0.5h;100%
With N-chloro-succinimide; copper(II) chloride monohydrate In acetonitrile at 82℃; for 10.5h; regioselective reaction;99.6%
With iodine; mercury dichloride; copper dichloride In acetic acid at 60℃; for 3h;98%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

allylindium sesquiiodide

allylindium sesquiiodide

2,3-benzo-1-allyl-1-hydroxycyclohexa-2,5-dien-4-one
20490-14-6

2,3-benzo-1-allyl-1-hydroxycyclohexa-2,5-dien-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at -23℃; for 3h;100%
ethyl 1-acetamido-3-cyclopentene-3-vinyl-1-carboxylate
207294-54-0

ethyl 1-acetamido-3-cyclopentene-3-vinyl-1-carboxylate

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-acetylamino-6,11-dioxo-2,3,5,6,11,11b-hexahydro-1H-cyclopenta[a]anthracene-2-carboxylic acid ethyl ester

2-acetylamino-6,11-dioxo-2,3,5,6,11,11b-hexahydro-1H-cyclopenta[a]anthracene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With hydroquinone In toluene for 48h; Diels-Alder reaction; Heating;100%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

1,4-Bis-hept-(E)-ylidene-2,5-bis-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexane

1,4-Bis-hept-(E)-ylidene-2,5-bis-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexane

(5aR,6S,11R,11aS)-8-Hept-(E)-ylidene-11-hexyl-6-trimethylsilanyl-9-[1-trimethylsilanyl-meth-(E)-ylidene]-5a,6,7,8,9,10,11,11a-octahydro-naphthacene-5,12-dione

(5aR,6S,11R,11aS)-8-Hept-(E)-ylidene-11-hexyl-6-trimethylsilanyl-9-[1-trimethylsilanyl-meth-(E)-ylidene]-5a,6,7,8,9,10,11,11a-octahydro-naphthacene-5,12-dione

Conditions
ConditionsYield
In benzene Diels-Alder reaction; Heating;100%
pentanal
110-62-3

pentanal

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2,3-dihydro-3-propylnaphtho[1,2-b]furan-2,5-diol

2,3-dihydro-3-propylnaphtho[1,2-b]furan-2,5-diol

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In ethanol; water at -24℃;100%
pine pitch

pine pitch

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

(1R,4aR,4bS,6R,6aR,12aR,12bS)-16-isopropyl-1,4a-dimethyl-7,12-dioxo-1,2,3,4,4a,4b,5,6,6a,7,12,12a,12b,13,14,14a,-hexadecahydro-6,12b-etheno[b]chrysene-1-carboxylic acid

(1R,4aR,4bS,6R,6aR,12aR,12bS)-16-isopropyl-1,4a-dimethyl-7,12-dioxo-1,2,3,4,4a,4b,5,6,6a,7,12,12a,12b,13,14,14a,-hexadecahydro-6,12b-etheno[b]chrysene-1-carboxylic acid

Conditions
ConditionsYield
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In hexane; dichloromethane at 20℃; for 5h; Reactivity; Reagent/catalyst; Solvent; Darkness;100%
ethylene glycol
107-21-1

ethylene glycol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

4-(2-hydroxyethoxy)-1-naphthol
83115-56-4

4-(2-hydroxyethoxy)-1-naphthol

Conditions
ConditionsYield
In toluene at 120℃; for 1h;100%
2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-(2,2-dimethoxyethylamino)-1,4-naphthoquinone
1038964-30-5

2-(2,2-dimethoxyethylamino)-1,4-naphthoquinone

Conditions
ConditionsYield
With cerium(III) chloride heptahydrate In acetonitrile at 20℃; for 24h; Sonication;100%
cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

endo-tetracyclo[10.2.2.02,11.04.9]hexadeca-4,6,8,13-tetraene-3,10-dione
132016-30-9

endo-tetracyclo[10.2.2.02,11.04.9]hexadeca-4,6,8,13-tetraene-3,10-dione

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In acetone for 40h; Ambient temperature;99%
With scandium tris(trifluoromethanesulfonate); 1-n-butyl-3-methylimidazolium hexafluoroantimonate In dichloromethane at 20℃; for 0.5h; Diels-Alder reaction;96%
With [O=P(2-py)3W(CO)(NO)2](BF4)2; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 8h; Diels-Alder reaction;93%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

isoprene
78-79-5

isoprene

2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione
3319-24-2, 55511-73-4

2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In acetone for 4h; Ambient temperature;99%
In methanol at 120℃; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique;95%
In 1-methyl-pyrrolidin-2-one at 190℃; under 750.075 Torr; for 0.0833333h; Diels-Alder reaction; Microwave irradiation; Inert atmosphere; Continuous-flow;52%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione
24402-95-7

1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione

Conditions
ConditionsYield
With benzylidene phenylamine; ytterbium(III) triflate In dichloromethane at 0℃; for 24h; Diels-Alder reaction;99%
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In dichloromethane at -20℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Diels-Alder Cycloaddition;96%
In propan-1-ol at 25℃; Thermodynamic data; Rate constant; other solvents and their mixture with water; isobaric activation parameters;
2-methoxyethylamine
109-85-3

2-methoxyethylamine

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-<(2-methoxyethyl)amino>-1,4-naphthoquinone
155859-95-3

2-<(2-methoxyethyl)amino>-1,4-naphthoquinone

Conditions
ConditionsYield
In ethanol for 65h; Ambient temperature;99%
With triethylamine In tetrahydrofuran75%
2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2,3-dimethyl-1,4,4a,9a-tetrahydro-9,10-anthracenedione
2670-23-7

2,3-dimethyl-1,4,4a,9a-tetrahydro-9,10-anthracenedione

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In acetone for 1h; Ambient temperature;99%
With tin-tungsten mixed oxide, Sn/W molar ratio = 2, calcined at 800 °C In dichloromethane at 20℃; for 1h; Diels-Alder reaction; Inert atmosphere;97%
With tetradecafluorohexane In water at 50℃; for 6h; Diels-Alder Cycloaddition;93%
trans-2-methyl-1,3-pentadiene
926-54-5

trans-2-methyl-1,3-pentadiene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

(1R,4aS,9aR)-1,3-Dimethyl-1,4,4a,9a-tetrahydro-anthraquinone

(1R,4aS,9aR)-1,3-Dimethyl-1,4,4a,9a-tetrahydro-anthraquinone

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In acetone for 1h; Ambient temperature;99%
ethyl 1-acetamido-3-cyclopentene-3-vinyl-1-carboxylate
207294-54-0

ethyl 1-acetamido-3-cyclopentene-3-vinyl-1-carboxylate

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-Acetylamino-6,11-dioxo-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene-2-carboxylic acid ethyl ester
207294-73-3

2-Acetylamino-6,11-dioxo-2,3,5,5a,6,11,11a,11b-octahydro-1H-cyclopenta[a]anthracene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
In benzene for 24h; Heating;99%
ethyl 1-acetamido-3,4-dimethylenecyclohepta-1-carboxylate
209258-60-6

ethyl 1-acetamido-3,4-dimethylenecyclohepta-1-carboxylate

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

9-acetylamino-5,13-dioxo-5a,6,7,8,9,10,11,12,12a,13-decahydro-5H-cyclohepta[b]anthracene-9-carboxylic acid ethyl ester
365224-00-6

9-acetylamino-5,13-dioxo-5a,6,7,8,9,10,11,12,12a,13-decahydro-5H-cyclohepta[b]anthracene-9-carboxylic acid ethyl ester

Conditions
ConditionsYield
In benzene for 120h; Diels-Alder reaction; Heating;99%
2-(triisopropylsiloxy)-1,3-butadiene
139278-54-9

2-(triisopropylsiloxy)-1,3-butadiene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

(4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-anthracene-9,10-dione

(4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-anthracene-9,10-dione

Conditions
ConditionsYield
(S)-oxazaborolidine-aluminum bromide at -78℃; for 16h; Diels-Alder reaction;99%
With oxazaborolidinium(1+)*Tf2N(1-) In dichloromethane at -78℃; for 2h; Diels-Alder reaction;98%

130-15-4Related news

Cytotoxicity of synthesized 1,4-Naphthoquinone (cas 130-15-4) analogues on selected human cancer cell lines09/30/2019

In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxici...detailed

Comparison of lung damage in mice exposed to black carbon particles and 1,4-Naphthoquinone (cas 130-15-4) coated black carbon particles10/01/2019

Black carbon (BC) is a key component of atmospheric particles and has a significant effect on human health. BC can provide reactive sites and surfaces thus absorb quinones which were primarily generated from fossil fuel combustion and/or atmospheric photochemical conversions of PAHs. Oxidation c...detailed

Ultrasound-assisted reaction of 1,4-Naphthoquinone (cas 130-15-4) with anilines through an EDA complex09/27/2019

Naphthoquinone amino derivatives exhibit interesting physicochemical properties and a wide range of biological activities with potential medicinal applications. A clean, fast and simple method for the preparation of phenylamino-1,4-naphthoquinones is presented by the reaction of naphthoquinone (...detailed

Antiplatelet and antithrombotic activities of CP201, a newly synthesized 1,4-Naphthoquinone (cas 130-15-4) derivative09/26/2019

The antiplatelet and antithrombotic activities of a newly synthesized CP201, 2-(3,5-di-tert-butyl-4-hydroxyl)-3-chloro-1,4-naphthoquinone on human platelet aggregation in vitro and murine pulmonary thrombosis in vivo were examined. In addition, the antiplatelet activity of CP201 involved in calc...detailed

Pharmacological and biological evaluation of a series of substituted 1,4-Naphthoquinone (cas 130-15-4) bioreductive drugs09/25/2019

The indolequinone compound EO9 has good pharmacodynamic properties in terms of bioreductive activation and selectivity for either NAD(P)H:quinone oxidoreductase-1 (NQO1)-rich aerobic or NQO1-deficient hypoxic cells. However, its pharmacokinetic properties are poor and this fact is believed to be...detailed

130-15-4Relevant articles and documents

The Formation of 1,4-Quinones by Oxovanadium(IV)-Complexes Catalyzed Aerobic Oxygenation of Fused Aromatic Compounds

Takai, Toshihiro,Hata, Eiichiro,Mukaiyama, Teruaki

, p. 885 - 888 (1994)

In the presence of a catalytic amount of oxovanadium(IV) complexes coordinated with 1,3-diketone ligands, fused aromatic compounds such as naphthalenes and naphthol derivatives are smoothly oxygenated into the corresponding 1,4-naphthoquinones by combined use of molecular oxygen and crotonaldehyde under an atmospheric pressure.

2-Pyridyldimethylsilyl Group as a Removable Hydrophilic Group in Aqueous Organic Reactions: Formation of Molecular Aggregates and Dramatic Rate Enhancement in Diels-Alder Reactions

Itami, Kenichiro,Nokami, Toshiki,Yoshida, Jun-Ichi

, p. 441 - 451 (2002)

A novel methodology for aqueous organic reactions utilizing a 2-pyridyldimethylsilyl (2-PyMe2Si) group as a removable hydrophilic group has been developed. It was found that 1,3-dienes bearing the 2-PyMe2Si group form molecular aggregates in water when 1.0 equivalent of HCl was added, as evidenced by dynamic light-scattering experiments. The Diels-Alder reaction of 2-PyMe2Si-substituted 1,3-dienes with various dienophiles took place in water at room temperature. The Diels-Alder reaction in organic solvents (Et2O/toluene) under the same reaction temperature and time gave the cycloadduct in much lower yield, indicating the dramatic rate acceleration in water. The removal of the 2-PyMe2Si group was accomplished by desilylation, oxidation, and electrophilic substitution.

Sodium hypochlorite/Dowex 1X8-200: An effective oxidant for the oxidation of aromatic amines to quinones

Hashemi, Mohammed M.,Beni, Yousef A.

, p. 672 - 673 (1999)

Polymer supported hypochlorite ion is a useful oxidant for the oxidation of aromatic amines to the corresponding quinones.

Influence of the sulfinyl group on the chemoselectivity and π-facial selectivity of diels-alder reactions of (S)-2-(p Tolylsulfinyl)-1,4-benzoquinone

Carreno, M. Carmen,Garcia Ruano, José L.,Toledo, Miguel A.,Urbano, Antonio,Remor, Cynthia Z.,Stefani, Valter,Fischer, Jean

, p. 503 - 509 (1996)

Diels-Alder reactions of (S)-2-(p-tolylsulfmyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyelohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C2-C3 versus C5-C6 double bonds) is mainly related to the cyclic (on C5-C6) or acyclic (on C2-C3) structure of the diene. The high π-facial selectivity observed could be controlled by choosing adequate experimental conditions.

Preparation and photocatalytic activity of WO3-MWCNT nanocomposite for degradation of naphthalene under visible light irradiation

Farhadian, Mousa,Sangpour, Parvaneh,Hosseinzadeh, Ghader

, p. 39063 - 39073 (2016)

In this study, a WO3-multiwalled carbon nanotube nanocomposite has been prepared for the first time by in situ liquid phase process. The prepared nanocomposite was used for photodegradation of dilute solution of naphthalene under visible light irradiation. Based on our results, comparing photocatalytic activity of WO3 nanoparticle with WO3-multiwalled carbon nanotube nanocomposite showed that the photodegradation of naphthalene is negligible by using pure WO3 nanoparticles while, composition of WO3 nanoparticles with multi walled carbon nanotubes could improve significantly their photocatalytic activity under visible light. Due to its high electrical conductivity, carbon nanotube can transfer photogenerated electron on its surface and in this way decreases electron-hole recombination rate and increases photocatalytic activity. After the reaction, the irradiated solution has been analyzed by gas chromatography and mass spectrometry techniques for identification of the naphthalene photodegradation intermediates and products. 1-Naphthol, 1,4-naphthalenedione and 1,2-benzendicarboxilic acid have been determined as intermediates and based on these intermediates a suitable mechanism for photodegradation of naphthalene was suggested.

-

Arnold,Larson

, p. 250 (1940)

-

Direct photooxidation and xanthene-sensitized oxidation of naphthols: Quantum yields and mechanism

Oelgemoeller, Michael,Mattay, Jochen,Goerner, Helmut

, p. 280 - 285 (2011)

The photoinduced oxidation of 1-naphthol to 1,4-naphthoquinone and of 5-hydroxy-1-naphthol to 5-hydroxy-1,4-naphthoquinone was studied by steady-state and time-resolved techniques. The direct photooxidation of naphthols in methanol or water takes place by reaction of the naphoxyl radical ( ·ONaph) with the superoxide ion radical (O2 ·-), the latter of which results from the reaction of the solvated electron with oxygen after photoionization. The sensitized oxidation takes place by energy transfer from the xanthene triplet state to oxygen. From the two oxygen atoms, which are consumed, one is incorporated into the naphthol molecule giving naphthoquinone and the second gives rise to water. The effects of eosin, erythrosin, and rose bengal in aqueous solution, pH, and the oxygen and naphthol concentrations were studied. The quantum yield of the photosensitized transformation was determined, which increases with the naphthol concentration and is largest at pH > 10. The quantum yield of oxygen uptake is similar. The pathway involving singlet molecular oxygen is suggested to operate for the three sensitizers. The alternative pathway via electron transfer from the naphthol to the xanthene triplet state and subsequent reaction of ·ONaph with O2·-, the latter of which is formed by scavenging of the xanthene radical anion by oxygen, does also contribute.

Polymer incarcerated gold catalyzed aerobic oxidation of hydroquinones and their derivatives

Miyamura, Hiroyuki,Shiramizu, Mika,Matsubara, Ryosuke,Kobayashi, Shu

, p. 360 - 361 (2008)

Polymer-incarcerated gold (PI Au) cluster catalysts mediated aerobic oxidation of hydroquinones and catechols to quinones very efficiently under mild conditions. The characteristic role of water in the reaction system was also observed. Copyright

Oxidation of Methoxy- and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H2O2 in HCOOH

Orita, Hideo,Shimizu, Masao,Hayakawa, Takashi,Takehira, Katsuomi

, p. 1652 - 1657 (1989)

The oxidation of a number of arenes (methoxybenzenes, methylbenzenes, and naphthalenes) to quinones and phenols by H2O2 in HCOOH has been examined.Methoxybenzenes were much more easily oxidized to p-benzoquinones than methylbenzenes (e.g., 1,3,5-trimethoxybenzene was oxidized to 2,6-dimethoxy-p-benzoquinone in a 75percent yield and 1,2,4-trimethylbenzene to 2,3,5-trimethyl-p-benzoquinone in a 16percent yield).Electron-withdrawing substituents, such as nitro, cyano, and chloro groups, lowered the conversion of reactants and changed the product selectivity from quinones to phenols.Methoxybenzonitriles were oxidized to corresponding phenols in a moder ate yield (e.g., 2,6-dimethoxybenzonitrile to 3-hydroxy-2,6-dimethoxybenzonitrile in a 39percent yield and a 64percent selectivity).

-

Periasamy,M.,Bhatt,M.V.

, p. 330 - 332 (1977)

-

Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors

Cui, Jiahua,Jia, Jinping

, (2021)

SARS-CoV-2 as a positive-sense single-stranded RNA coronavirus caused the global outbreak of COVID-19. The main protease (Mpro) of the virus as the major enzyme processing viral polyproteins contributed to the replication and transcription of SARS-CoV-2 in host cells, and has been characterized as an attractive target in drug discovery. Herein, a set of 1,4-naphthoquinones with juglone skeleton were prepared and evaluated for the inhibitory efficacy against SARS-CoV-2 Mpro. More than half of the tested naphthoquinones could effectively inhibit the target enzyme with an inhibition rate of more than 90% at the concentration of 10 μM. In the structure-activity relationships (SARs) analysis, the characteristics of substituents and their position on juglone core scaffold were recognized as key ingredients for enzyme inhibitory activity. The most active compound, 2-acetyl-8-methoxy-1,4-naphthoquinone (15), which exhibited much higher potency in enzyme inhibitions than shikonin as the positive control, displayed an IC50 value of 72.07 ± 4.84 nM towards Mpro-mediated hydrolysis of the fluorescently labeled peptide. It fit well into the active site cavity of the enzyme by forming hydrogen bonds with adjacent amino acid residues in molecular docking studies. The results from in vitro antiviral activity evaluation demonstrated that the most potent Mpro inhibitor could significantly suppress the replication of SARS-CoV-2 in Vero E6 cells within the low micromolar concentrations, with its EC50 value of about 4.55 μM. It was non-toxic towards the host Vero E6 cells under tested concentrations. The present research work implied that juglone skeleton could be a primary template for the development of potent Mpro inhibitors.

Visible-light induced solvent-free photooxygenations of organic substrates by using [60]fullerene-linked silica gels as heterogeneous catalysts and as solid-phase reaction fields

Hino, Tetsuo,Anzai, Takahiro,Kuramoto, Noriyuki

, p. 1429 - 1432 (2006)

Novel recyclable heterogeneous catalysts generating singlet-oxygen under visible-light irradiation have been prepared by linking [60]fullerene to amino-functionalized silica gels. The catalysts facilitate various types of photooxygenerations including Diels-Alder reaction, ene reaction, and oxidations of phenol and sulfide in a solid-solvent system and even in a solvent-free system.

Convenient Synthesis of 1,4-Naphthoquinones from Polymethoxynaphthalenes. Oxidative Demethylation with Silver-Catalyzed Ammonium Peroxodisulfate

Tanoue, Yasuhiro,Sakata, Kazunori,Hashimoto, Mamoru,Morishita, Shin-ichi,Hamada, Moritsugu

, p. 2593 - 2595 (1994)

The oxidative demethylation of polymethoxynaphthalenes such as 1,4-di, 1,4,5-tri, 1,4,5,8-tetra-, and 1,2,4,5,8-pentamethoxynaphthalenes with silver-catalyzed ammonium peroxodisulfate gave the corresponding 1,4-naphthoquinones in good yield under mild reaction conditions.

Immobilization of a Metal Complex in Y-Zeolite Matrix: Synthesis, X-ray Single-Crystal, and Catalytic Activities of a Copper (Schiff-Base)-Y Zeolite Based Hybrid Catalyst

Saha, Pratap Kumar,Banerjee, Surajit,Saha, Sandip,Mukherjee, Alok Kumar,Sivasanker, Subramanian,Koner, Subratanath

, p. 709 - 714 (2004)

A new zeolite-immobilized copper(II) complex catalyst has been prepared by entrapping [CuL] [LH2 = N,N′ -(1,1-dimethylethylene)bis(salicylaldiimine)] on NaY zeolite matrix. The reaction of Cu-NaY and molten LH2 affords a green mass of crude catalyst that upon a treatment with CH3CN gives a gray-colored hybrid catalyst (CuL-NaY). The prepared catalyst has been characterized by IR and UV-vis spectroscopic and EPR spectrometric measurements, TG-DTA analysis, powder X-ray diffraction, and surface-area measurements. To ascertain the structure of the immobilized complex, a single-crystal X-ray diffraction analysis of [CuL] was performed. Spectroscopic measurements showed that the green crude of CuL-NaY contains a penta- or hexa-coordinated copper(II) moiety, while the CuL-NaY catalyst contains a distorted square-planar [CuL] complex moiety. A remarkable catalytic activity of the prepared hybrid catalyst has been observed in oxidation reactions of 1-naphthol and norbornene.

Strategies for cleaner oxidations using photochemically generated singlet oxygen in supercritical carbon dioxide

Han, Xue,Bourne, Richard A.,Poliakoff, Martyn,George, Michael W.

, p. 1787 - 1792 (2009)

Photochemically generated singlet oxygen, 1O2, has been reacted with four different substrates in supercritical carbon dioxide. By using fluorous surfactants and a co-solvent to solubilise more polar photosensitisers and reactants respectively, the applicability of the system is greatly enhanced. The Royal Society of Chemistry 2009.

Molecular growth of PAH-like systems induced by oxygen species: Experimental and theoretical study of the reaction of naphthalene with HO (2Π3/2), O (3P), and O2 (3Σ - G)

Scapinello, Marco,Martini, Luca Matteo,Tosi, Paolo,Maranzana, Andrea,Tonachini, Glauco

, p. 38581 - 38590 (2015)

To assess if reactions with oxygen species can induce a mass increase of polycyclic aromatic hydrocarbons, we exposed naphthalene molecules to an oxidative gas flow containing the radicals H and HO (2Π3/2) and the diradicals O (3P) and O2 (3Σ-g). We observed the formation of 1- and 2-naphtol, 1,4-naphthoquinone, naphthalene-derived cyclic ethers, an ester from ring opening, and ether adducts containing two naphthalene units. We investigated the possible reaction pathways as a function of temperature by density functional calculations. We found that the reactivity is characterized by HO, O and H addition to naphthalene, or by H abstraction from it, with roles depending on temperature. In conclusion, oxygen species can promote, under the experimental conditions, mainly naphthalene oxidation and, to a lesser extent, substantial molecular growth, with an efficiency that the calculations indicate to depend on the system temperature. Future experiments should try to quantify key species to allow defining the relative importance of the various reaction mechanisms uncovered by ab initio calculations.

2-Geranyl-1,4-naphthoquinone, a possible intermediate of anthraquinones in a Sesamum indicum hairy root culture

Furumoto, Toshio,Ohara, Tomoko,Kubo, Tetsuya,Kawanami, Yasuhiro,Fukui, Hiroshi

, p. 2600 - 2602 (2007)

2-Geranyl-1,4-naphthoquinone was isolated from the hairy root culture of Sesamum indicum. The structure was determined to be 2-[(E)-3,7-dimethylocta-2,6- dienyl]-1,4-naphthoquinone on the basis of spectroscopic evidence and chemical synthesis. The production of anthrasesamones A, B and C by the hairy root culture was also confirmed for the first time.

Copper-mediated addition of ethanolamine affording 2-hydroxymethyl naphtho[2,1-d]oxazoles from 2-naphthols

Wang, Xiuzhen,Yang, Baoyun,Li, Rui

, p. 846 - 849 (2014)

A new and mild synthetic approach was presented for the synthesis of naphtho[2,1-d]oxazoles. In the presence of copper (II)-ethanolamine, 2-hydroxymethyl naphtho[2,1-d]oxazoles were one-pot synthesized in moderate to good yields through copper-mediated oxidation of 2-naphthols followed with the addition of ethanolamine in acetonitrile.

Anodic oxidation of 4-methoxy-1-naphthol

El-Seedi, Hesham R.,Yamamura, Shosuke,Nishiyama, Shigeru

, p. 3301 - 3304 (2002)

Anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles provided the corresponding products 8-12 and the dimers 13 and 17 were also produced. The reaction mechanism of the oxidation reaction including the [3+2] cycloaddition was investigated.

Thermolysis of 2-Benzylidenebenzocyclobutenols

Bradley, Jean-Claude,Durst, Tony,Williams, A. J.

, p. 6575 - 6579 (1992)

The thermolysis of a series of 2-benzylidenebenzocyclobuten-1-ols has been studied.Whenever comparisons can be made, the rate of opening of the benzocyclobutene ring was slower for these compounds than the corresponding 2-ones.The intermediate vinylallenes underwent a variety of electrocyclization reactions which depended on the nature of the additional substituent at C-1. 10-Benzylideneanthrone and 4-benzylidene-1-tetralones, respectively, were obtained when this substituent was phenyl or vinyl. 1-(Alkynylphenyl)-2-benzylidenebenzocylobuten-1-ols were converted to mixtures of 4-benzylidene-1,4-naphthoquinonemethides, 2,3-dibenzylidene-1-indanones, and 10-phenylbenzofluorenone.

Photooxygenations of 1-naphthols: An environmentally friendly access to 1,4-naphthoquinones

Suchard, Oliver,Kane, Ronan,Roe, Bernard J.,Zimmermann, Elmar,Jung, Christian,Waske, Prashant A.,Mattay, Jochen,Oelgem?ller, Michael

, p. 1467 - 1473 (2006)

Dye sensitized photooxygenations of 1-naphthols were investigated with soluble and solid-supported sensitizers and moderate to excellent yields of the corresponding 1,4-naphthoquinones were achieved in relatively short irradiation times. The mild and environmentally friendly reaction conditions made this application particularly attractive for 'Green Photochemistry'. Consequently, the photooxygenation of 1,5-dihydroxynaphthalene was studied with non-concentrated and moderately concentrated sunlight and 5-hydroxy-1,4- naphthoquinone (Juglone) was obtained in yields up to 71%.

Homogeneous oxidation of aromatics in nucleus with peracetic acid catalyzed by iron and manganese phthalocyanine complexes

Barkanova, Svetlana V.,Derkacheva, Valentina M.,Dolotova, Olga V.,Li, Vladimir D.,Negrimovsky, Vladimir M.,Kaliya, Oleg L.,Luk'yanets, Eugene A.

, p. 1637 - 1640 (1996)

The reaction of naphthalene and methylnaphthalenes with peracetic acid catalyzed by Mn(III) (1) or Fe(II) (2) octanitrophthalocyanines in CH3CN at 20°C produces 1,4-naphthoquinones with 35-62% yields. The corresponding 2,3-epoxide-1,4-endoperoxides are proposed as intermediate in reaction catalyzed by 1.

μ-oxo-bridged hypervalent iodine(III) compound as an extreme oxidant for aqueous oxidations

Dohi, Toshifumi,Nakae, Tomofumi,Takenaga, Naoko,Uchiyama, Teruyoshi,Fukushima, Kei-Ichiro,Fujioka, Hiromichi,Kita, Yasuyuki

, p. 1183 - 1189 (2012)

We have found that in aqueous oxidations the -oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF]} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. -Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble -oxo oxidant 1, which has promise for -oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate). Georg Thieme Verlag Stuttgart New York.

Efficient oxidative ipso-fluorination of para-substituted phenols using pyridinium polyhydrogen fluoride in combination with hypervalent iodine(III) reagents

Karam, Omar,Martin-Mingot, Agnès,Jouannetaud, Marie-Paule,Jacquesy, Jean-Claude,Cousson, Alain

, p. 6629 - 6638 (2004)

Diacetoxyiodobenzene (PIDA) and bis(trifluoroacetoxy)iodobenzene (PIFA) in the presence of pyridinium polyhydrogen fluoride (PPHF) are effective for the fluorination of para-substituted phenols to give a variety of 4-fluorocyclohexa-2,5-dienones in a good yield. (R,S)-1,1′-Bi-5,6,7,8- tetrahydro-2-naphthol (and its monoacetate) yields atropoisomeric fluorocyclohexadienones. The 4-substituted carbamate open-chain phenols were readily converted to fluorohydroindolenone and fluorohydroquinolenone derivatives by intramolecular conjugate addition.

Synthesis, properties and singlet oxygen generation of thiazolidinone double bond linked porphyrin at meso and β-position

Ahmad, Sohail,Yadav, Kumar Karitkey,Narang, Uma,Bhattacharya, Soumee,Singh, Sarangthem Joychandra,Chauhan

, p. 36090 - 36095 (2016)

Meso and β-substituted free base and zinc metallated thiazolidinone-porphyrin conjugates were synthesized by one pot four component Knoevenagel condensation by utilizing substituted amines, carbon disulfide, ethyl chloroacetate and porphyrin aldehydes. These newly synthesized conjugates were characterized by IR, 1H NMR, 13C NMR, UV-Vis, fluorescence and HRMS spectroscopy. The singlet oxygen generation behaviors of these porphyrin conjugates were studied and it was observed that these porphyrin conjugates followed type II singlet oxygen. Fluorescence and singlet oxygen quantum yields among meso-substituted (mono-, di, tetra) and β-substituted conjugates were examined. The photocatalytic photooxidation of naphthols and furan by using these new organic photocatalysts were further analysed and it was observed that meso-tetra substituted (Zn3a) and β-substituted (Zn6a) porphyrins are much efficient for generation of singlet oxygen and for photocatalytic photooxidation.

PHOTOOXIDATION OF PHENOLIC COMPOUNDS

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Page/Page column 18, (2021/11/26)

The present invention relates to the photooxidation of phenolic compounds to the respective quinoid compounds using methylene blue as photosensitizer in a solvent mixture of water and alcohols using light of the high wavelength range of the visible spectrum.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

Hu, Rong-Bin,Lam, Ying-Pong,Ng, Wing-Hin,Wong, Chun-Yuen,Yeung, Ying-Yeung

, p. 3498 - 3506 (2021/04/07)

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

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