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124-13-0

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124-13-0 Usage

Description

May be prepared by oxidation of the corresponding alcohol or reduction of the corresponding acid; also from coconut fatty acids via methyl-n-octanoate.

Chemical Properties

Different sources of media describe the Chemical Properties of 124-13-0 differently. You can refer to the following data:
1. n-Octanal has a fatty, citrus, honey odor on dilution.
2. liquid
3. Octanal occurs in several citrus oils, for example, orange oil. It is a colorless liquid with a pungent odor, which becomes citrus-like on dilution. Octanal is used in perfumery in low concentrations, in eau de cologne, and in artificial citrus oils.

Occurrence

Reported found in the essential oils of sweet orange, bitter orange, mandarin, tangerine, grapefruit, Mexican lime, lemon, Taiwan citronella, rose, lemongrass, Pinus sabiniana, Pinus jefferyi, Xanthoxylum rhetsa, lime petitgrain, clary sage, lavandin, and others. Also reported in over 180 foods and beverages including apple, apricot, many berries, guava, grapes, melon, papaya, celery, peas, potato, potato chips, tomato, ginger, spearmint oil, cheeses, butter, milk, cooked egg, fish and fish oil, meats, hop oil, beer, rum, cider, white wine, cocoa, tea, roasted filberts and peanuts, pecans, oats, coconut products, soybean, avocado, passion fruit, starfruit, beans, mushroom, trassi, macadamia nut, sesame seed, mango, cauliflower, tamarind, fig, calamus, rice, sweet potato, dill, lovage, caraway seed, corn oil, corn tortillas, loquat, shrimp, lobster, oyster, crab, crayfish, clam, maté, angelica root oil and mastic gum oil.

Uses

Octanal is an aromatic aldehyde often found in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry.

Preparation

By oxidation of the corresponding alcohol or reduction of the corresponding acid; also from coconut fatty acids via methyl-n-octoate.

Definition

ChEBI: A fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid).

Aroma threshold values

Detection: 1.4 to 6.4 ppb

Taste threshold values

Taste characteristics at 25 ppm: aldehyde, green with a peely, citrus, orange note.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 3837, 1977 DOI: 10.1021/ja00453a053Journal of Heterocyclic Chemistry, 29, p. 257, 1992 DOI: 10.1002/jhet.5570290148Tetrahedron Letters, 36, p. 2247, 1995 DOI: 10.1016/0040-4039(95)00262-B

General Description

Colorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125°F. Used in making perfumes and flavorings.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

OCTYL ALDEHYDES are aldehydes. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Safety Profile

Mildly toxic by ingestion and skin contact. A skin and eye irritant. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. See also ALDEHYDES.

Metabolism

Aldehydes C-8, C-10, C-12 and C-14 (myristic), the lower unsubstituted aliphatic aldehydes, are readily oxidized in the animal body to the corresponding fatty acids, which normally undergo oxidation and are eventially oxidized to carbon dioxide and water.

Check Digit Verification of cas no

The CAS Registry Mumber 124-13-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 124-13:
(5*1)+(4*2)+(3*4)+(2*1)+(1*3)=30
30 % 10 = 0
So 124-13-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3

124-13-0 Well-known Company Product Price

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  • CAS number
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  • TCI America

  • (O0044)  n-Octanal  >98.0%(GC)

  • 124-13-0

  • 25mL

  • 120.00CNY

  • Detail
  • TCI America

  • (O0044)  n-Octanal  >98.0%(GC)

  • 124-13-0

  • 500mL

  • 670.00CNY

  • Detail
  • Sigma-Aldrich

  • (52466)  Octanal  analytical standard

  • 124-13-0

  • 52466-1ML

  • 458.64CNY

  • Detail
  • Sigma-Aldrich

  • (52466)  Octanal  analytical standard

  • 124-13-0

  • 52466-5ML

  • 1,880.19CNY

  • Detail

124-13-0SDS

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 octanal

1.2 Other means of identification

Product number -
Other names Octanal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
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:124-13-0 SDS

124-13-0Synthetic route

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With methanesulfonic acid; tributylphosphine; copper; zinc In acetonitrile for 1h; Product distribution; Ambient temperature; reactions of other acid chlorides; solvent-effect; effect of var. metals;100%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;96%
With pumice stone; platinum at 195℃; under 80 - 90 Torr; Hydrogenation;
((E)-4-Oct-1-enyl)-morpholine
155127-38-1

((E)-4-Oct-1-enyl)-morpholine

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With aq. acid for 1h; Ambient temperature;100%
2-heptyl-[1,3]dithiane
59092-72-7

2-heptyl-[1,3]dithiane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;100%
With silica gel; copper(II) nitrate In tetrachloromethane for 0.416667h; Ambient temperature;98%
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 68h;85%
octanol
111-87-5

octanol

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With chromium (VI) oxide In toluene for 0.416667h; microwave irradiation;99%
With N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; potassium carbonate; 4 A molecular sieve In dichloromethane at 20℃; for 3h;99%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h;99%
octanol
111-87-5

octanol

2,5-dimethoxybenzyl alcohol
33524-31-1

2,5-dimethoxybenzyl alcohol

A

Octanal
124-13-0

Octanal

B

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

Conditions
ConditionsYield
With air; potassium carbonate at 20℃; for 16h;A 2%
B 99%
octanal 1,3-dithiolane
93215-67-9

octanal 1,3-dithiolane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.25h; Ambient temperature;98%
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;96%
With bismuth(III) nitrate; water In benzene at 20℃; for 4h;98 % Chromat.
oct-1-ene
111-66-0

oct-1-ene

carbon monoxide
201230-82-2

carbon monoxide

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With (acetylacetonato)dicarbonylrhodium (l); C43H53O8P; hydrogen In toluene under 37503.8 Torr; for 12h; Catalytic behavior; regioselective reaction;97.1%
With Ca8(PO4)3.5(HPO4)2.5(OH)0.5; hydrogen; Rh2(μ-S-t-Bu)2(CO)2(P(C6H4SO3Na)3)2 In toluene at 80℃; under 3750.38 Torr; for 3h; Product distribution; Further Variations:; Reagents; hydration rate of reagent;93%
octanal oxime
929-55-5

octanal oxime

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 1.66667h; Heating;97%
With ammonium peroxydisulfate; Montmorillonite K10; silver nitrate In hexane at 50℃; for 2.5h;94%
With water; Dess-Martin periodane In dichloromethane at 5℃; for 0.5h;92%
4-methyl-N'-octylidenebenzene-1-sulfonohydrazide
69873-64-9

4-methyl-N'-octylidenebenzene-1-sulfonohydrazide

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 2h; Heating;97%
octanol
111-87-5

octanol

A

Octanal
124-13-0

Octanal

B

octyl octylate
2306-88-9

octyl octylate

Conditions
ConditionsYield
With 5-ethyl-2-methyl-pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate In dichloromethane for 1h; Reagent/catalyst;A 96.6%
B 3.4%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; tert.-butylnitrite; oxygen In 1,2-dichloro-ethane under 1500.15 Torr; for 6h; Autoclave; Heating;A 94%
B 1%
With water; oxygen at 100℃; under 3750.38 Torr; for 18h; Autoclave;A 9%
B 91%
n-octyne
629-05-0

n-octyne

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With sodium dodecyl-sulfate; [Ru(η5-C9H7(Cl(PPh3)2] In water at 60℃; for 24h;95%
With chloro(cyclopentadienyl)[bis(diphenylphosphino)methane]ruthenium; water In isopropyl alcohol at 100℃; for 12h;93%
With borane N,N-diethylaniline complex; dihydrogen peroxide; sodium acetate; benzo[1,3,2]dioxaborole 1.) benzene, 25 deg C, 24 h; Yield given. Multistep reaction;
trimethyl(oct-1-yloxy)silane
14246-16-3

trimethyl(oct-1-yloxy)silane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;95%
With chromium(VI) oxide; HZSM-5 zeolite for 0.025h; microwave irradiation;93%
With chromium(VI) oxide; Hexamethyldisiloxane; silica gel In dichloromethane for 0.333333h; Ambient temperature;89%
n-Octylamine
111-86-4

n-Octylamine

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
Stage #1: n-Octylamine With tungsten(IV) sulfide at 46℃; for 3h;
Stage #2: With isobutyl formate for 1.83333h; Temperature; Reflux;
94%
With potassium hydroxide In ethyl acetate at -78℃; Product distribution;39%
Multi-step reaction with 3 steps
1: 98 percent / Et3N / CH2Cl2 / 1 h / 0 °C
2: N-tert-butylphenylsulfinimidoyl chloride; DBU / CH2Cl2 / 1 h / -78 °C
3: HCl; H2O / diethyl ether; CH2Cl2 / 2 h / 50 °C
View Scheme
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

A

octanol
111-87-5

octanol

B

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With phosphate buffer; D-glucose; Synechococcus sp. PCC 7942; Triton X-100 In water at 25℃; for 72h; pH=7.0; Irradiation;A 94%
B 5%
trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine
122744-71-2

trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine

A

Octanal
124-13-0

Octanal

B

α-Heptyl-N-benzylnitrone
72552-76-2

α-Heptyl-N-benzylnitrone

C

benzoic acid
65-85-0

benzoic acid

D

Benzaldoxime
932-90-1

Benzaldoxime

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 24h; Ambient temperature; other base;A 18%
B 49%
C 93%
D 20%
octylidene diacetate
23162-72-3

octylidene diacetate

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With H6P2W18O62 In toluene at 100℃; for 0.0833333h;93%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 20℃; for 3.5h; chemoselective reaction;86%
Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); trifluorormethanesulfonic acid; carbon monoxide; N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine; hydrogen In dichloromethane at 40℃; under 15001.5 Torr; for 3h; Autoclave; chemoselective reaction;93%
With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; under 15001.5 Torr; for 24h; chemoselective reaction;82%
With dibenzylammonium trifluoroacetate salt In dichloromethane at 20℃; for 24h;82 %Chromat.
With hydrogen; sodium dodecyl-sulfate; palladium diacetate In tetrahydrofuran; water at 20℃; under 750.075 Torr; for 1h; Reagent/catalyst; chemoselective reaction;
octanol
111-87-5

octanol

A

Octanal
124-13-0

Octanal

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 12h; in air;A 92%
B 5.2%
With Succinimide; sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate In ethyl acetate at 0 - 10℃; for 2h;A 86%
B 7%
With potassium chromate; copolyesteramide (from N,N'-bis(4-methoxycarbonylbenzoyl)hexamethylenediamine, 1,6-hexanediol, poly(ethylene glycol)); sulfuric acid In dichloromethane at -5℃; for 0.25h;A 83%
B 2.1%
1,1-dimethoxyoctane
10022-28-3

1,1-dimethoxyoctane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
indium(III) chloride In methanol; water for 1.16667h; Heating;92%
1,3-di(NCS)-tetrabutyldistannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h; Deprotection of acetal;85%
With titanium tetrachloride; lithium iodide In diethyl ether for 3h; Product distribution; Ambient temperature;85%
Tetrabutyl-1,3-diisothiocyanato-distannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h;85%
2-bromooctanal
35066-22-9

2-bromooctanal

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With DMBI In tetrahydrofuran for 5h; Heating;92%
oct-7-en-1-ol
13175-44-5

oct-7-en-1-ol

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With potassium hydroxide; PS-resin; potassium hexacyanoferrate(III); 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl In water; toluene at 20℃; for 24h;92%
N'-octylidene-N,N-dimethyl-hydrazine
99178-22-0

N'-octylidene-N,N-dimethyl-hydrazine

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With Glyoxilic acid In water at 20℃; for 4h;91%
tin(ll) chloride; palladium dichloride In water for 0.025h; microwave irradiation;88%
2-heptyl-1,3-dioxolane
4359-57-3

2-heptyl-1,3-dioxolane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
indium(III) chloride In methanol; water for 1.33333h; Heating;90%
1,3-di(NCS)-tetrabutyldistannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h; Deprotection of acetal;87%
Tetrabutyl-1,3-diisothiocyanato-distannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h;87%
1-(pyrrolidin-1-yl)nonan-1-one
20308-70-7

1-(pyrrolidin-1-yl)nonan-1-one

A

octanol
111-87-5

octanol

B

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 1h; Ambient temperature; Yield given;A n/a
B 90%
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 1h; Ambient temperature; Yields of byproduct given;A n/a
B 90%
N,N-diethyloctanamide
996-97-4

N,N-diethyloctanamide

A

octanol
111-87-5

octanol

B

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 1h; Ambient temperature; Yields of byproduct given;A n/a
B 90%
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 0.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

3-methylthio-5-octyl-1,4-diphenyl-1,2,4-triazolium iodide
63318-32-1

3-methylthio-5-octyl-1,4-diphenyl-1,2,4-triazolium iodide

A

iodobenzene
591-50-4

iodobenzene

B

Octanal
124-13-0

Octanal

C

1,4-Diphenyl-3-methylmercapto-1,2,4-triazolium iodide
13136-15-7

1,4-Diphenyl-3-methylmercapto-1,2,4-triazolium iodide

Conditions
ConditionsYield
With sulfuric acid; iodine; sodium methylate; potassium iodide 1.) CHCl3, 2.) MeOH, room temp, 15 min; Yield given. Multistep reaction;A 90%
B n/a
C 31%
1-bromo-octane
111-83-1

1-bromo-octane

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With dimethyl sulfoxide for 0.0638889h; Kornblum oxidation; Microwave irradiation;89%
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 0.75h;85%
With sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide at 115℃; for 2h;60%
With silver(I) 4-methylbenzenesulfonate; acetonitrile Erhitzen mit Dimethylsulfoxyd und Natriumhydrogencarbonat auf 150grad;
With 4-(dimethylamino)pyridine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) CH3CN, reflux, 15 min, 2.) CH3CN, reflux, 40 min; Yield given. Multistep reaction;
trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine
122744-71-2

trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine

A

Octanal
124-13-0

Octanal

B

α-Heptyl-N-benzylnitrone
72552-76-2

α-Heptyl-N-benzylnitrone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane for 0.5h; Product distribution; Ambient temperature;A 44%
B 28%
C 89%
((octyloxy)methyl)benzene
54852-64-1

((octyloxy)methyl)benzene

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With tert.-butylhydroperoxide; chromium-pillared montmorillonite In 2,2,4-trimethylpentane; dichloromethane for 18h; Ambient temperature;88%
nitromethane
75-52-5

nitromethane

Octanal
124-13-0

Octanal

2-hydroxy-1-nitrononane
4013-87-0

2-hydroxy-1-nitrononane

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; butan-1-ol at 23℃; Inert atmosphere;100%
With silica gel; triethylamine at 20℃; for 3h; Henry Nitro Aldol Condensation;95%
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 20℃; for 18.5h; Henry reaction;94%
Octanal
124-13-0

Octanal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxyoctane
10022-28-3

1,1-dimethoxyoctane

Conditions
ConditionsYield
With lithium tetrafluoroborate In methanol for 0.5h; Heating;100%
With cerium triflate In methanol at 20℃; for 0.0166667h;95%
With Pd(PhCN)2(OTf)2 at 20℃; for 0.333333h; Inert atmosphere;90%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Octanal
124-13-0

Octanal

ethyl (E)-2-decenate
7367-88-6

ethyl (E)-2-decenate

Conditions
ConditionsYield
With n-butyllithium In 1,2-dimethoxyethane; hexane 1.) 0 deg C, 10 min, 2.) 30 min;100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In diethyl ether at 0℃; for 0.0833333h;
Stage #2: Octanal In diethyl ether for 0.25h;
96%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In diethyl ether; mineral oil at 0℃;
Stage #2: Octanal In diethyl ether; mineral oil at 0℃;
96%
Octanal
124-13-0

Octanal

(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

((S)-2-Methoxymethyl-pyrrolidin-1-yl)-oct-(E)-ylidene-amine
72170-92-4

((S)-2-Methoxymethyl-pyrrolidin-1-yl)-oct-(E)-ylidene-amine

Conditions
ConditionsYield
at 20℃; for 16h;100%
Yield given;
Octanal
124-13-0

Octanal

tetraallyl tin
7393-43-3

tetraallyl tin

1-undecen-4-ol
13891-96-8

1-undecen-4-ol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃; for 1h;100%
With C20H23BBiF4N In methanol; water at 20℃; for 1h;95%
With C17H18BiF3O5S In methanol at 20℃; for 1h;92%
Octanal
124-13-0

Octanal

methylamine hydrochloride
593-51-1

methylamine hydrochloride

potassium cyanide
151-50-8

potassium cyanide

2-Methylamino-nonanenitrile
112101-12-9

2-Methylamino-nonanenitrile

Conditions
ConditionsYield
With aluminum oxide In acetonitrile at 50℃; for 22h; ultrasound;100%
Octanal
124-13-0

Octanal

octanol
111-87-5

octanol

Conditions
ConditionsYield
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 13h;100%
With zirconium(IV) tetraisopropoxide 2-propanol; 4 Angstroem MS; 1,1'-bi-2-naphthol In isopropyl alcohol; toluene at 20℃; for 18h;100%
With zirconium(IV) tetraisopropoxide 2-propanol; 1,1'-bi-2-naphthol In toluene at 20℃; for 1h;100%
cyclopent-2-enone
930-30-3

cyclopent-2-enone

Octanal
124-13-0

Octanal

2-(1-hydroxy-octyl)-cyclopent-2-enone

2-(1-hydroxy-octyl)-cyclopent-2-enone

Conditions
ConditionsYield
With tributylphosphine; 1,1'-bi-2-naphthol In tetrahydrofuran at 20℃; for 3h; Baylis-Hillman addition;100%
Octanal
124-13-0

Octanal

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

C14H20N4O4

C14H20N4O4

Conditions
ConditionsYield
100%
Octanal
124-13-0

Octanal

Diethyl maleate
141-05-9

Diethyl maleate

2-Octanoylbutandisaeure-diethylester
73642-72-5

2-Octanoylbutandisaeure-diethylester

Conditions
ConditionsYield
With 4-cyanobenzaldehyde In Petroleum ether at 20℃; for 16h; Reagent/catalyst; Sealed tube; Irradiation;100%
With dibenzoyl peroxide
With dibenzoyl peroxide
1-pentylisonitrile
18971-59-0

1-pentylisonitrile

Octanal
124-13-0

Octanal

C22H43NO3
1032198-35-8

C22H43NO3

Conditions
ConditionsYield
With water; sodium sulfate at 20℃; for 7h; Passerini Condensation;100%
With air; water at 40℃; for 3h;71%
homoalylic alcohol
627-27-0

homoalylic alcohol

Octanal
124-13-0

Octanal

cis-2-heptyl-4-fluorotetrahydro-2H-pyran

cis-2-heptyl-4-fluorotetrahydro-2H-pyran

Conditions
ConditionsYield
With Et4NF*5HF at 20℃; for 0.166667h; Prins reaction; stereoselective reaction;100%
With Et4NF*5HF at 20℃; for 0.166667h; Prins cyclization; stereoselective reaction;
Octanal
124-13-0

Octanal

1-undecen-4-ol
13891-96-8

1-undecen-4-ol

cis-4-fluoro-2,6-diheptyltetrahydropyran
1070331-37-1

cis-4-fluoro-2,6-diheptyltetrahydropyran

Conditions
ConditionsYield
With Et4NF*5HF at 20℃; for 0.166667h; Prins reaction; stereoselective reaction;100%
With Et4NF*5HF at 20℃; for 0.166667h; Prins cyclization; stereoselective reaction;
Octanal
124-13-0

Octanal

2Br(1-)*C26H32NO2P(2+)

2Br(1-)*C26H32NO2P(2+)

ethyl (E)-2-decenate
7367-88-6

ethyl (E)-2-decenate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 40℃; for 24h; Wittig reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;100%
Octanal
124-13-0

Octanal

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

C20H39NO3
944882-97-7

C20H39NO3

Conditions
ConditionsYield
In methanol for 3h; Reflux;100%
Octanal
124-13-0

Octanal

ethyl isocyano formate

ethyl isocyano formate

C21H39NO5
1032198-30-3

C21H39NO5

Conditions
ConditionsYield
With water; sodium sulfate at 20℃; for 7h; Passerini Condensation;100%
2-oxoindole
59-48-3

2-oxoindole

Octanal
124-13-0

Octanal

C16H21NO

C16H21NO

Conditions
ConditionsYield
Reagent/catalyst; Aldol Condensation; Inert atmosphere;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 5%

acetylated chitosan, degree of acetylation 5%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 5%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 5%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Microwave irradiation;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 5%

acetylated chitosan, degree of acetylation 5%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 10%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 10%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Temperature; Time; Microwave irradiation;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 5%

acetylated chitosan, degree of acetylation 5%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 20%

methylated acetylated chitosan, degree of acetylation 5%, alkylation 20%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Temperature; Time; Microwave irradiation;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 25%

acetylated chitosan, degree of acetylation 25%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 5%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 5%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Microwave irradiation;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 25%

acetylated chitosan, degree of acetylation 25%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 10%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 10%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Temperature; Time; Microwave irradiation;100%
Octanal
124-13-0

Octanal

acetylated chitosan, degree of acetylation 25%

acetylated chitosan, degree of acetylation 25%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 20%

methylated acetylated chitosan, degree of acetylation 25%, alkylation 20%

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol; water; acetic acid at 40℃; for 1h; Temperature; Time; Microwave irradiation;100%
Octanal
124-13-0

Octanal

(1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol
1354483-32-1

(1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol

C37H49NO3

C37H49NO3

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In ethanol at 20℃; for 6h;100%
methanesulfonic acid
75-75-2

methanesulfonic acid

Octanal
124-13-0

Octanal

C9H17O3S(1-)*Na(1+)

C9H17O3S(1-)*Na(1+)

Conditions
ConditionsYield
With sodium butanolate In butan-1-ol Reflux;100%
Octanal
124-13-0

Octanal

1,1-diacetoxy-1-(2-chlorophenyl)methane
13086-95-8

1,1-diacetoxy-1-(2-chlorophenyl)methane

1-(2-chlorophenyl)-2-oxononyl acetate

1-(2-chlorophenyl)-2-oxononyl acetate

Conditions
ConditionsYield
With 2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux;100%
Octanal
124-13-0

Octanal

[2-methyl-2-phenyl-1,3-oxazolidin-4-yl]methanol
944883-07-2

[2-methyl-2-phenyl-1,3-oxazolidin-4-yl]methanol

1-aza-3,7-dioxa-2-phenylacetyl-8-octylbicyclo[3.3.0]octane

1-aza-3,7-dioxa-2-phenylacetyl-8-octylbicyclo[3.3.0]octane

Conditions
ConditionsYield
99.9%

124-13-0Relevant articles and documents

Rhodium thiolate hydroformylation complexes tethered to delamellated γ-zirconium phosphate

Rojas,Murcia-Mascaros,Terreros,Garcia Fierro

, p. 1430 - 1437 (2001)

Rhodium thiolate complexes intercalated in crystalline γ-zirconium phosphate or tethered to SiO2-modified γ-zirconium phosphate have been synthesised. It was observed that the addition of a solution of organic silicates to a colloidal suspension of γ-zirconium phosphate yielded amorphous substrates, which displayed very high specific areas (160-650 m2 g-1). Incorporation of a mercaptocarbonyl rhodium complex resulted in a highly selective and active catalyst precursor for the hydroformylation of 1-heptene in the liquid phase. Elemental analysis and photoelectron spectroscopy of the fresh and used samples revealed that some metal leaching occurs during the reaction, this being mainly confined to the outer layers of the solid particles. This observation, together with the high selectivity towards linear aldehydes, makes SiO2-modified γ-zirconium phosphate a good support candidate for immobilised Rh catalysts. Spectroscopic data obtained from the crystalline precursor and also from the amorphous catalyst showed that the interaction between the rhodium complex and the acid support was achieved via hydrogen bonds, forming NH groups.

Heterogeneous selective oxidation of fatty alcohols: Oxidation of 1-tetradecanol as a model substrate

Corberán, Vicente Cortés,Gómez-Avilés, Almudena,Martínez-González, Susana,Ivanova, Svetlana,Domínguez, María I.,González-Pérez, María Elena

, p. 49 - 53 (2014)

s Selective oxidation of fatty alcohols, i.e., linear long-chain alkanols, has been scarcely investigated to date, despite its potential application in high value chemical's production. We report for the first time the liquid phase heterogeneous oxidation of 1-tetradecanol, used as a model molecule for fatty alcohols, according to green chemistry principles by using a Au/CeO2-Al2O3 catalyst and O2 as oxidant at normal pressure. High selectivity to tetradecanal (ca. 80%) or to tetradecanoic acid (60-70%) are reached at medium conversion (up to 38%), depending on the reaction conditions used. Comparison with similar tests of 1-octanol oxidation shows that the increase of the carbon chain length decreases the alcohol conversion and the formation of ester, probably due to a greater steric effect.

Coprecipitated gold-trieobalt tetraoxide catalyst for heterogeneous hydroformylation of oleflns

Liu, Xiaohao,Haruta, Masatake,Tokunaga, Makoto

, p. 1290 - 1291 (2008)

The combination of gold (Au0) and tricobalt tetraoxide (CO 3O4) prepared by coprecipitation gives high-performance heterogeneous catalysts for hydroformylation reaction with selectivity above 85% in desired aldehydes, alth

Synthesis of two new Mo(II) organometallic catalysts immobilized on POSS for application in olefin oxidation reactions

Vieira, Eduardo Guimar?es,Dal-Bó, Alexandre Gon?alves,Frizon, Tiago Elias Allievi,Dias Filho, Newton Luiz

, p. 73 - 82 (2017)

The purpose of this work was the preparation and characterization of two new catalysts POSS-ATZAc-[Mo(η3-C3H5)Br(CO)2] (POSS-Mo-I) and POSS-ATZAc-[Mo(CO)3Br2] (POSS-Mo-II). The new heterogeneous catalysts were characterized by several techniques and used as catalysts for the epoxidation of olefins, presenting high catalytic activity. To study and optimize the syntheses of the heterogeneous catalysts, immobilization experiments of the [Mo(η3-C3H5)Br(CO)2(NCMe)2] and [Mo(CO)3Br2(NCMe)2] organometallic complexes on the modified polyhedral oligomeric silsesquioxane were performed. The sorption properties of the modified silsesquioxane showed to be dependent of the contact time, concentration and temperature. Catalysts were tested in the epoxidation of six olefins and compared with homogeneous species [Mo(η3-C3H5)Br(CO)2(ATZAc)] (Mo-I) and [Mo(CO)3Br2(ATZAc)] (Mo-II). To the best of our knowledge, this paper is the first that has reported the preparation and characterization of two new heterogeneous catalysts, as well as the comparison with homogeneous species for catalytic epoxidation of olefins.

Readily Accessible 12-I-5 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones

Dess, D. B.,Martin, J. C.

, p. 4155 - 4156 (1983)

Periodinane 2 is a mild, selective reagent for the oxidation of primary and secondary alcohols to aldehydes and ketones.

REDOX REACTIONS IN MICELLAR SYSTEMS. COMMUNICATION 1. REDUCTION OF METHYL VIOLOGEN BY KETYL RADICAL

Burbo, E.M.,Gasanova, L.V.,Dzhabiev, T.S.

, p. 2246 - 2251 (1984)

-

Au/TiO2 catalysts promoted with Fe and Mg for n-octanol oxidation under mild conditions

Kotolevich,Kolobova,Mamontov,Khramov,Cabrera Ortega,Tiznado,Farías,Bogdanchikova,Zubavichus, Ya.,Mota-Morales,Cortés Corberán,Zanella,Pestryakov

, p. 104 - 112 (2016)

This work aims to further the understanding of gold-based catalytic oxidation of n-octanol in liquid phase. Modification of catalysts with metal oxides additives (Fe or Mg) was used as a tool for transforming and stabilizing gold species. Structural, electronic and catalytic properties of gold catalysts were systematically investigated by means of DRS, H2, CO FTIR, SBET, EDS and SEM, HRTEM, SR-XRD, XANES, XPS and liquid phase n-octanol oxidation. Addition of modifiers affects Au electronic properties, but not the structural ones. Characterization results allow excluding Au3+ ions as candidates for active sites in n-octanol oxidation. In Au/Mg/TiO2, gold exhibited more reduced states while in Au/Fe/TiO2 gold was more oxidized; Au/TiO2 for intermediate oxidized states was found. The proper balance of oxidation states in the gold surface of Au/Mg/TiO2 can be responsible for its higher activity compared with Au/Fe/TiO2 and Au/TiO2 towards n-octanol oxidation. Finally our approach shed light on the nature of active sites for n-octanol oxidation on gold and furthers the development of green base-free catalytic oxidation of alcohols.

Room temperature liquid salts of Cr and Mo as self-supported oxidants

Noguera, Gladys,Mostany, Jorge,Agrifoglio, Giuseppe,Dorta, Romano

, p. 231 - 234 (2005)

Room temperature liquid salts of Cr and Mo were synthesized and fully characterized including cyclic voltammetry of the neat Mo salt. These liquid salts were used as self-supported reagents for the oxidation of alcohols (under solvent-free and biphasic conditions) and their potential for biphasic self-supported catalytic applications was demonstrated.

ACTIVATION AND SYNTHETIC APPLICATIONS OF THIOSTANNANES. CHEMICAL MODIFICATION OF HYDROXY FUNCTION UNDER PROTECTION

Sato, Tsuneo,Tada, Tatsushi,Otera, Junzo,Nozaki, Hitosi

, p. 1665 - 1668 (1989)

Tetrahydropyranyl ethers are converted in one-pot into benzyl and α-methoxyethoxymethyl ethers, benzoates, tosylates, and aldehydes on treatment with thiostannanes in the presence of BF3*OEt2 followed by exposure of the resulting alkoxystannanes to electrophiles or PCC.

The effect of support properties on n-octanol oxidation performed on gold – silver catalysts supported on MgO, ZnO and Nb2O5

Kaskow, Iveta,Sobczak, Izabela,Ziolek, Maria,Corberán, Vicente Cortés

, (2020)

Catalytic behaviour of supported nanometal catalysts for alcohols selective oxidation depends on the nature of the support and its surface. To identify the main feature that could explain these effects, supported mono- (Au) and bimetallic (AuAg) catalysts were prepared by using pure MgO, ZnO and Nb2O5, representative of three different types of oxides (basic, amphoteric and acidic, respectively), to get homogeneous metal-support interaction for each catalyst. The catalysts were characterized by XRD, N2 physisorption, TEM, UV–vis, XPS and 2-propanol decomposition as test reaction. It was found that the catalytic activity is influenced by the electron mobility between the gold nanoparticles and the support, which in turns depends on the intermediate electronegativity of the support. Selectivity in n-octanol oxidation was determined by redox properties of the gold species, the acid-base properties of the supports and the catalyst pretreatment. Silver addition modified the acid-base properties of the catalytic system, thus influencing the selectivity in n-octanol oxidation. Pretreatment of the catalyst (drying in air or thermal treatment in hydrogen flow) had a significant impact on its activity and selectivity.

Hydroformylation of 1-hexene over rhodium supported on active carbon catalyst

Li, Baitao,Li, Xiaohong,Asami, Kenji,Fujimoto, Kaoru

, p. 378 - 379 (2003)

Hydroformylation of 1-hexene on rhodium catalyst was studied under mild reaction conditions (P = 3.0 MPa, CO/H2 = 1/1, T = 403 K). Its hydroformylation performances were investigated in a variety of solvent. It was found that the excellent activity for the heterogeneous catalyst was showed in the n-octane solvent, while poor activity in the alcoholic and H2O solvent.

Pyridinium chlorochromate: An improved method for its synthesis and use of anhydrous acetic acid as catalyst for oxidation reactions

Agarwal, Seema,Tiwari,Sharma

, p. 4417 - 4420 (1990)

An improved procedure for the preparation of Corey's reagent - Pyridinium chlorochromate has been described. The method is less hazardous and gives better yield. Synthetic utility of the reagent has been shown to increase in the presence of anhydrous acetic acid, used for the first time as catalyst, for the oxidation of alcohols.

Not as easy as π: An insertional residue does not explain the π-helix gain-of-function in two-component FMN reductases

McFarlane, Jeffrey S.,Hagen, Richard A.,Chilton, Annemarie S.,Forbes, Dianna L.,Lamb, Audrey L.,Ellis, Holly R.

, p. 123 - 134 (2019)

The π-helix located at the tetramer interface of two-component FMN-dependent reductases contributes to the structural divergence from canonical FMN-bound reductases within the NADPH:FMN reductase family. The π-helix in the SsuE FMN-dependent reductase of the alkanesulfonate monooxygenase system has been proposed to be generated by the insertion of a Tyr residue in the conserved α4-helix. Variants of Tyr118 were generated, and their X-ray crystal structures determined, to evaluate how these alterations affect the structural integrity of the π-helix. The structure of the Y118A SsuE π-helix was converted to an α-helix, similar to the FMN-bound members of the NADPH:FMN reductase family. Although the π-helix was altered, the FMN binding region remained unchanged. Conversely, deletion of Tyr118 disrupted the secondary structural properties of the π-helix, generating a random coil region in the middle of helix 4. Both the Y118A and Δ118 SsuE SsuE variants crystallize as a dimer. The MsuE FMN reductase involved in the desulfonation of methanesulfonates is structurally similar to SsuE, but the π-helix contains a His insertional residue. Exchanging the π-helix insertional residue of each enzyme did not result in equivalent kinetic properties. Structure-based sequence analysis further demonstrated the presence of a similar Tyr residue in an FMN-bound reductase in the NADPH:FMN reductase family that is not sufficient to generate a π-helix. Results from the structural and functional studies of the FMN-dependent reductases suggest that the insertional residue alone is not solely responsible for generating the π-helix, and additional structural adaptions occur to provide the altered gain of function.

Triruthenium dodecacarbonyl/triphenylphosphine catalyzed dehydrogenation of primary and secondary alcohols

Meijer,Ligthart,Meuldijk,Vekemans,Hulshof,Mills,Kooijman,Spek

, p. 1065 - 1072 (2004)

Dehydrogenation of alcohols into aldehydes and ketones by Ru 3(CO)12/PPh3 based homogeneous catalysis has been investigated as an alternative for the classical Oppenauer oxidation. Several catalytic systems have been screened in the Oppenauer-like oxidation of alcohols. A systematic study of various combinations of Ru3(CO) 12, mono- and bidentate ligands and hydride acceptors was performed to enable dehydrogenation of primary alcohols to stop at the aldehyde stage. Among many H-acceptors screened, diphenylacetylene (tolane) proved the most suitable judged from its smooth reduction. Electron rich and deficient analogues of tolane have been synthesized and, based on competition experiments between these H-acceptors, a tentative catalytic cycle for the Ru 3(CO)12/PPh3-catalyzed dehydrogenations has been proposed.

Asymmetric synthesis of (-)-acaterin

Kandula, Subba Rao V.,Kumar, Pradeep

, p. 6149 - 6151 (2003)

The asymmetric synthesis of (-)-acaterin, an inhibitor of acyl-CoA cholesterol acyl transferase has been achieved starting from the commercially available starting materials, octan-1-ol and methyl (R)-lactate. The key steps are a Sharpless asymmetric dihydroxylation and a Wittig olefination.

One-Pot Bioelectrocatalytic Conversion of Chemically Inert Hydrocarbons to Imines

Chen, Hui,Tang, Tianhua,Malapit, Christian A.,Lee, Yoo Seok,Prater, Matthew B.,Weliwatte, N. Samali,Minteer, Shelley D.

, p. 4047 - 4056 (2022/02/10)

Petroleum hydrocarbons are our major energy source and an important feedstock for the chemical industry. With the exception of combustion, the deep conversion of chemically inert hydrocarbons to more valuable chemicals is of considerable interest. However, two challenges hinder this conversion. One is the regioselective activation of inert carbon-hydrogen (C-H) bonds. The other is designing a pathway to realize this complicated conversion. In response to the two challenges, a multistep bioelectrocatalytic system was developed to realize the one-pot deep conversion from heptane to N-heptylhepan-1-imine under mild conditions. First, in this enzymatic cascade, a bioelectrocatalytic C-H bond oxyfunctionalization step based on alkane hydroxylase (alkB) was applied to regioselectively convert heptane to 1-heptanol. By integrating subsequent alcohol oxidation and bioelectrocatalytic reductive amination steps based on an engineered choline oxidase (AcCO6) and a reductive aminase (NfRedAm), the generated 1-heptanol was successfully converted to N-heptylhepan-1-imine. The electrochemical architecture provided sufficient electrons to drive the bioelectrocatalytic C-H bond oxyfunctionalization and reductive amination steps with neutral red (NR) as electron mediator. The highest concentration of N-heptylhepan-1-imine achieved was 0.67 mM with a Faradaic efficiency of 45% for C-H bond oxyfunctionalization and 70% for reductive amination. Hexane, octane, and ethylbenzene were also successfully converted to the corresponding imines. Via regioselective C-H bond oxyfunctionalization, intermediate oxidation, and reductive amination, the bioelectrocatalytic hydrocarbon deep conversion system successfully realized the challenging conversion from inert hydrocarbons to imines that would have been impossible by using organic synthesis methods and provided a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.

Expanding the Biocatalytic Toolbox with a New Type of ene/yne-Reductase from Cyclocybe aegerita

Karrer, Dominik,Gand, Martin,Rühl, Martin

, p. 2191 - 2199 (2021/02/26)

This study introduces a new type of ene/yne-reductase from Cyclocybe aegerita with a broad substrate scope including aliphatic and aromatic alkenes/alkynes from which aliphatic C8-alkenones, C8-alkenals and aromatic nitroalkenes were the preferred substrates. By comparing alkenes and alkynes, a ~2-fold lower conversion towards alkynes was observed. Furthermore, it could be shown that the alkyne reduction proceeds via a slow reduction of the alkyne to the alkene followed by a rapid reduction to the corresponding alkane. An accumulation of the alkene was not observed. Moreover, a regioselective reduction of the double bond in α,β-position of α,β,γ,δ-unsaturated alkenals took place. This as well as the first biocatalytic reduction of different aliphatic and aromatic alkynes to alkanes underlines the novelty of this biocatalyst. Thus with this study on the new ene-reductase CaeEnR1, a promising substrate scope is disclosed that describes conceivably a broad occurrence of such reactions within the chemical landscape.

Visible light-induced photodeoxygenation of polycyclic selenophene Se-oxides

Chintala, Satyanarayana M.,Throgmorton, John C.,Maness, Peter F.,McCulla, Ryan D.

, (2020/10/02)

Photodeoxygenation of dibenzothiophene S-oxide (DBTO) is believed to produce ground-state atomic oxygen [O(3P)] in solution. Compared with other reactive oxygen species (ROS), O(3P) is a unique oxidant as it is potent and selective. Derivatives of DBTO have been used as O(3P)-precursors to oxidize variety of molecules, including plasmid DNA, proteins, lipids, thiols, and other small organic molecules. Unfortunately, the photodeoxygenation of DBTO requires ultraviolet irradiation, which is not an ideal wavelength range for biological systems, and has a low quantum yield of approximately 0.003. In this work, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide, and perylo[1,12-b,c,d]selenophene Se-oxide were synthesized, and their ability to utilize visible light for generating O(3P) was interrogated. Benzo[b]naphtho[1,2-d]selenophene Se-oxide produces O(3P) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, and dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide produce O(3P) when irradiated with UVA light and have quantum yields of photodeoxygenation ranging from 0.009 to 0.33. This work increases the utility of photodeoxygenation by extending the range of wavelengths that can be used to generate O(3P) in solution.

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