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1896-62-4

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1896-62-4 Usage

Chemical Properties

light yellow low melting crystalline mass or

Uses

trans-4-Phenyl-3-buten-2-one is used in various synthetic preparations.

Definition

ChEBI: The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.

General Description

trans-4-Phenyl-3-buten-2-one forms trans-4-(4-hydroxyphenyl)-3-buten-2-one (4-OH-PBO) as a metabolite when incubated with liver microsomes of untreated rats in the presence of NADPH.

Safety Profile

Mutation data reported. Aflammable liquid. When heated to decomposition it emitsacrid smoke and irritating vapors.

Check Digit Verification of cas no

The CAS Registry Mumber 1896-62-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,9 and 6 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1896-62:
(6*1)+(5*8)+(4*9)+(3*6)+(2*6)+(1*2)=114
114 % 10 = 4
So 1896-62-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+

1896-62-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name trans-benzylideneacetone

1.2 Other means of identification

Product number -
Other names benzylidene-2,4,6-trimethylacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:1896-62-4 SDS

1896-62-4Synthetic route

3-methyl-5-phenyl-4,5-dihydro-1H-pyrazole
939-03-7

3-methyl-5-phenyl-4,5-dihydro-1H-pyrazole

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With benzeneseleninic anhydride In dichloromethane for 4h; Ambient temperature;100%
(E)-2-methyl-2-styryl-1,3-dioxolane
63511-95-5

(E)-2-methyl-2-styryl-1,3-dioxolane

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With Ru(CH3CN)3(triphos)(OTf)2 (triphos = CH3C(CH2PPh2)3); acetone for 48h; Ambient temperature;100%
With hydrogenchloride; water In dimethyl sulfoxide at 20℃; Inert atmosphere;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

N-methoxy-N-methylcinnamamide
80783-99-9, 124931-15-3, 113474-86-5

N-methoxy-N-methylcinnamamide

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;98%
Stage #1: N-methoxy-N-methylcinnamamide With methyl 4-bromocinnamate; triethylsilyl trifluoromethyl sulfonate; triethylphosphine In toluene at 110℃; for 5h; Inert atmosphere;
Stage #2: methylmagnesium bromide In tetrahydrofuran; toluene at -78℃; Inert atmosphere;
Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene for 0.5h; Inert atmosphere;
83%
Diethyl (2-oxopropyl)phosphonate
1067-71-6

Diethyl (2-oxopropyl)phosphonate

benzaldehyde
100-52-7

benzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 15h;100%
With potassium carbonate In water at 20℃; for 18h;100%
With potassium carbonate In water at 20℃; for 18h; other aldehyde;100%
iodobenzene
591-50-4

iodobenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 18h; Heck reaction;100%
With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 48h;98%
With triphenylphosphine on reverse phase silica; triethylamine; Pd(OAc)2 on reverse phase silica In methanol; water Addition; Heck reaction;97%
2-methyl-2-trans-β-styryl-1,3-dithiane
72047-50-8

2-methyl-2-trans-β-styryl-1,3-dithiane

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 0.5h;100%
With [bis(acetoxy)iodo]benzene In water; acetone at 20℃; for 0.0333333h; Ring cleavage;90%
With o-iodoxybenzoic acid monohydrate In dimethyl sulfoxide at 22 - 32℃; for 16h;74%
With Dess-Martin periodane In dichloromethane; water; acetonitrile at 20℃; for 0.5h;
benzaldehyde
100-52-7

benzaldehyde

acetone
67-64-1

acetone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With sodium hydroxide In water for 7h;99%
With sodium hydroxide In water at 20℃; for 6h; Claisen-Schmidt Condensation;99%
With propylamine; Bi(S(CH2C6H4)2)(H2O)(1+)*CF3(CF2)6CF2SO3(1-)=[Bi(H2O)(S(CH2C6H4)2)](C8F17SO3) In water at 0 - 20℃; for 3h; Claisen-Schmidt condensation; optical yield given as %de; diastereoselective reaction;96%
ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; tris(2-methylphenyl)bismuth dichloride In toluene at 20℃; for 0.5h;99%
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 16h; in air;99%
With sodium hydroxide; dipotassium peroxodisulfate; nickel(II) sulphate In dichloromethane; water for 24h; Ambient temperature;96%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With [Rh(±)-2,2’-bis(diphenylphosphino)-1,1’-binaphthyl]BF4 In dichloromethane at 80℃; for 1h;99%
[Rh(±)-2,2’-bis(diphenylphosphino)-1,1’-binaphthyl]BF4 In 1,2-dichloro-ethane at 80℃; for 1h;99%
Multi-step reaction with 2 steps
1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C / Darkness; Schlenk technique
2: triphenylphosphine; benzoic acid; water / tetrahydrofuran / 24 h / 65 °C
View Scheme
N-(benzylidene)-p-methylbenzenesulfonamide
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In dimethyl sulfoxide at 100℃; for 12h; Inert atmosphere; optical yield given as %de; stereoselective reaction;99%
(Z)-4-phenylbut-3-en-2-one
937-53-1

(Z)-4-phenylbut-3-en-2-one

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
cuprate induced isomerization;98%
With bis(benzonitrile)palladium(II) dichloride In dichloromethane at 20℃; for 0.333333h;97%
Beim Erhitzen erfolgt Umwandlung;
cadmium(II) sulphide In dichloromethane Product distribution; Irradiation;
benzaldehyde
100-52-7

benzaldehyde

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In toluene Wittig Olefination; Reflux;98%
In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere; Reflux; optical yield given as %de;88%
In water at 20℃; for 1h; Wittig reaction;85%
In tetrahydrofuran at -78 - 20℃; Wittig Olefination; Inert atmosphere; stereoselective reaction;n/a
3,4-dibromo-4-phenylbutan-2-one
6310-44-7

3,4-dibromo-4-phenylbutan-2-one

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With indium; acetic acid; sodium sulfite In methanol at 20℃; for 0.333333h;97.1%
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;84%
With N,N-dimethyl-formamide In hydrogen fluoride at 160℃; for 1h;74%
1-phenylbut-2-yn-1-ol
32398-66-6

1-phenylbut-2-yn-1-ol

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-[bis(trifluoromethanesulfonyl)-imide]gold(I) In water; isopropyl alcohol at 40℃; for 2.5h; Meyer-Schuster Rearrangement;97%
With indium(III) chloride In water at 160℃; for 0.166667h; Meyer-Schuster rearrangement; Microwave irradiation; stereoselective reaction;89%
With methanol; (triphenylphosphine)gold(I) chloride; oxygen; silver(I) triflimide In dichloromethane at 25℃; for 24h;72%
iodobenzene
591-50-4

iodobenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

A

4-Phenyl-2-butanone
2550-26-7

4-Phenyl-2-butanone

B

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 120℃; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Heck Reaction; Overall yield = 100 %;A 3%
B 97%
palladated Kaiser oxime resin In water at 120℃; for 20h; Heck reaction;A 10%
B 82%
With 1-ethyl-3-methyl-1H-imidazol-3-ium methyl phosphonate at 150℃; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Heck Reaction; Overall yield = 100 %;A 80%
B 20%
benzaldehyde
100-52-7

benzaldehyde

chloroacetone
78-95-5

chloroacetone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 50℃; for 36h; Wittig reaction; optical yield given as %de;96%
With 2-propenamide; triphenylphosphine In propan-1-ol at 20 - 90℃; for 5h; Wittig reaction; Inert atmosphere; optical yield given as %de; stereoselective reaction;93%
With cerium(III) triiodide In tetrahydrofuran for 1h; Ambient temperature;80%
4-phenyl-3-butyne-2-one
1817-57-8

4-phenyl-3-butyne-2-one

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In water at 80℃; under 3750.38 Torr; for 4h; Autoclave; Schlenk technique; chemoselective reaction;96%
With formic acid; gold nanoparticles on rutile titania; triethylamine In acetone at 60℃; for 1h; stereoselective reaction;89%
With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water for 3h;
bromobenzene
108-86-1

bromobenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl-ammonium chloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Microwave irradiation;96%
With triethylamine In N,N-dimethyl-formamide at 100℃; for 18h; Heck reaction;88%
4-Phenyl-2-butanone
2550-26-7

4-Phenyl-2-butanone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 6h; Sealed tube;96%
With iron(III) chloride; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In chlorobenzene at 120℃; for 48h; Inert atmosphere; Schlenk technique;69%
Multi-step reaction with 2 steps
1: 2,6-dimethylpyridine / tetrahydrofuran / 1 h / 0 °C
2: eosin y; potassium acetate; oxygen / ethanol / 4 °C / Irradiation
View Scheme
With iodine; N,N-dimethyl-formamide; copper(II) oxide at 100℃; for 24h; Inert atmosphere;111 mg
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With hydrogenchloride In methanol at 25℃; for 24h;95%
With cerium(III) chloride; sodium iodide In acetonitrile for 10h; Dehydration; Heating;89%
In diethyl ether for 3h;
With hydrogenchloride In water at 60℃; for 1h;54.8 mg
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

Li(CH3SOCH2CuCH3)

Li(CH3SOCH2CuCH3)

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h;95%
2-methyl-2-trans-β-styryl-1,3-dithiane
72047-50-8

2-methyl-2-trans-β-styryl-1,3-dithiane

A

1.3-propanedithiol
109-80-8

1.3-propanedithiol

B

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With magnesium(II) perchlorate; water; methylene green In acetonitrile Irradiation;A n/a
B 94%
6-(tert-butyl)-12-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine
909413-25-8

6-(tert-butyl)-12-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With palladium dichloride In N,N-dimethyl acetamide at 80℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Heck Reaction;94%
(3-Oxo-1-phenyl-butyl)-triphenyl-phosphonium; perchlorate
43100-94-3

(3-Oxo-1-phenyl-butyl)-triphenyl-phosphonium; perchlorate

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With triethylamine In methanol; chloroform Ambient temperature;93%
ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

A

1-Phenyl-1,2-epoxy-butanol-(3)
4426-63-5

1-Phenyl-1,2-epoxy-butanol-(3)

B

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With oxo(salen)chromium(V)+ PF6- In dichloromethane at 20℃; for 1h; Product distribution; Further Variations:; Reagents; Oxidation; epoxidation;A n/a
B 93%
With CrIII(salen)(TfO) In dichloromethane at 20℃; for 1h; Product distribution; Further Variations:; Reagents; Oxidation; epoxidation;
benzaldehyde
100-52-7

benzaldehyde

acetone
67-64-1

acetone

A

1-hydroxy-1-phenyl-3-butanone
5381-93-1, 86734-67-0, 86734-69-2, 127707-68-0

1-hydroxy-1-phenyl-3-butanone

B

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With pyrrolidine In water for 0.0833333h;A 93%
B 6%
[Choline][Pro] In water at 20℃; for 12h;A 80.4%
B 8%
With sodium hydroxide In water for 7h;A 19%
B 77%
benzaldehyde
100-52-7

benzaldehyde

isopropyl alcohol
67-63-0

isopropyl alcohol

A

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
at 225℃; for 24h;A n/a
B 92%
benzaldehyde
100-52-7

benzaldehyde

A

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With isopropyl alcohol at 225℃; for 24h;A 2%
B 92%
With isopropyl alcohol at 225℃; for 24h;A n/a
B 92%
erythro-3.4-Dibrom-4-phenyl-butan-2-on
6310-44-7, 32147-15-2, 55025-54-2

erythro-3.4-Dibrom-4-phenyl-butan-2-on

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With indium; iron(III) chloride hexahydrate In methanol at 20℃; for 1h; chemoselective reaction;92%
With bismuth(III) chloride; gallium In tetrahydrofuran at 20℃; for 0.5h; stereoselective reaction;91%
With iron In methanol for 0.416667h; Dehalogenation; Heating;90%
benzaldehyde
100-52-7

benzaldehyde

(2-Methoxy-ethylidene)-triphenyl-λ5-phosphane

(2-Methoxy-ethylidene)-triphenyl-λ5-phosphane

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
In tetrahydrofuran for 20h; Wittig olefination; Heating;92%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

4-Phenyl-2-butanone
2550-26-7

4-Phenyl-2-butanone

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride; sodium formate In water; 1,2-dichloro-benzene at 108.9℃; for 0.166667h;100%
With dicobalt octacarbonyl; water In 1,2-dimethoxyethane for 2h; Heating;100%
With 1-ethyl-3-methyl-1H-imidazol-3-ium methyl phosphonate; hydrogen at 30℃; under 15001.5 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique;100%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

Conditions
ConditionsYield
With Zn(BH4)2(Ph3P)2 at 60℃; for 0.16h; Reduction;100%
With sodium tetrahydroborate In methanol for 2h; Cooling with ice;100%
With diisobutylaluminium hydride In hexane; toluene at -78℃; for 3h; or LiAlH(i-Bu)2(n-Bu);99%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(E)-4-phenyl-3-buten-2-one oxime
21613-44-5

(E)-4-phenyl-3-buten-2-one oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 1h;100%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 80℃; for 4h; Inert atmosphere; chemoselective reaction;59%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 5h; Heating;52%
iodobenzene
591-50-4

iodobenzene

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

4,4-diphenylbutan-2-one
5409-60-9

4,4-diphenylbutan-2-one

Conditions
ConditionsYield
With tributyl-amine; tetra-(n-butyl)ammonium iodide; trifluoroacetic acid; bis(triphenylphosphine) palladium (Il) acetate In N,N-dimethyl-formamide at 70℃;100%
With triethylamine; palladium diacetate In carbon dioxide at 80℃; under 75006 Torr; for 60h; Arylation; Hydroarylation;88%
1-(Trimethylsilyloxy)cyclohexene
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(3'-oxo-1'-phenylbutyl)-1-cyclohexanone
221363-48-0

2-(3'-oxo-1'-phenylbutyl)-1-cyclohexanone

Conditions
ConditionsYield
tin(IV) chloride; zinc(II) chloride In dichloromethane at -78℃; for 3h;100%
chloro-trimethyl-silane; tin(ll) chloride In dichloromethane at -78℃; for 13h;93%
With lithium perchlorate In nitromethane for 16h; Ambient temperature;85%
With hydrogenchloride; bismuth(III) chloride 1) CH2Cl2, rt, 6 h, 2) MeOH; Yield given. Multistep reaction;
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(2R,3E)-4-phenyl-3-buten-2-ol
62413-47-2

(2R,3E)-4-phenyl-3-buten-2-ol

Conditions
ConditionsYield
With (S,S)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); hydrogen; potassium carbonate In isopropyl alcohol at 28 - 30℃; under 60800 Torr; for 43h;100%
Stage #1: (E)-benzalacetone With C51H80N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran at 35℃; for 0.5h;
Stage #2: With potassium borohydride In tetrahydrofuran; water at 0℃; for 1.5h; enantioselective reaction;
99%
With benzo[1,3,2]dioxaborole; Oxazaborolidine 2 In toluene at -78℃; for 15h;95%
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(E)-triisopropyl((4-phenylbuta-1,3-dien-2-yl)oxy)silane
163811-53-8

(E)-triisopropyl((4-phenylbuta-1,3-dien-2-yl)oxy)silane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 8h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Schlenk technique;88%
With triethylamine In benzene at 20℃; for 2h;62%
In dichloromethane
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(1R,2R,6S)-2-Hydroxy-4-oxo-2,6-diphenyl-cyclohexanecarboxylic acid ethyl ester

(1R,2R,6S)-2-Hydroxy-4-oxo-2,6-diphenyl-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 50℃;100%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(E)-1,1,1-trifluoro-6-phenylhex-5-ene-2,4-dione
18931-64-1

(E)-1,1,1-trifluoro-6-phenylhex-5-ene-2,4-dione

Conditions
ConditionsYield
With sodium hydride at 40℃; for 3h;100%
With lithium hydride In benzene for 5h; Condensation;65%
phenylhydrazine
100-63-0

phenylhydrazine

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine
358723-67-8

(E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine

Conditions
ConditionsYield
at 20℃; for 0.0833333h;100%
With acetic acid In methanol at 20℃; Inert atmosphere;85%
With acetic acid In methanol for 0.75h; Heating;
With acetic acid In methanol at 20℃;
acetophenone
98-86-2

acetophenone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

A

(S)-1-phenylethanol
1445-91-6

(S)-1-phenylethanol

B

(R)-1-phenylethanol
1517-69-7

(R)-1-phenylethanol

Conditions
ConditionsYield
With Triethoxysilane; (S,S,S,S)-N,N'-di(α-phenylethyl)cyclohexane-1,2-diamine; diethylzinc In toluene at 20℃; for 18h; Title compound not separated from byproducts.;A n/a
B 100%
With polymethylhydrosiloxane; (S,S,S,S)-N,N'-di(α-phenylethyl)cyclohexane-1,2-diamine; diethylzinc In toluene at 20℃; for 24h; Title compound not separated from byproducts.;A n/a
B 90%
2-ethoxycarbonyl-1-tetralone
6742-26-3

2-ethoxycarbonyl-1-tetralone

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

methyl 1-oxo-2-(1-phenyl-3-oxobutyl)indan-2-carboxylate

methyl 1-oxo-2-(1-phenyl-3-oxobutyl)indan-2-carboxylate

Conditions
ConditionsYield
With polymer-micelle incarcerated Sc(OTf)3 In acetonitrile at 20℃; for 6h; Michael reaction;100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-chlorophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-chlorophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
Stage #1: 1H-indene-1,3(2H)-dione; 4-chlorobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation;
Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;
100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

1-naphthaldehyde
66-77-3

1-naphthaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
Stage #1: 1H-indene-1,3(2H)-dione; 1-naphthaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation;
Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;
100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-hydroxyphenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-hydroxyphenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
Stage #1: 1H-indene-1,3(2H)-dione; 4-hydroxy-benzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation;
Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;
100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-cyanophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-cyanophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
Stage #1: 1H-indene-1,3(2H)-dione; 4-cyanobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation;
Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;
100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

2-[4-(methoxycarbonyl)phenyl]-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-[4-(methoxycarbonyl)phenyl]-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
Stage #1: 1H-indene-1,3(2H)-dione; methyl 4-formylbenzoate With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation;
Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;
100%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

4-(4-methoxyphenyl)-4-phenylbutan-2-one
76217-07-7

4-(4-methoxyphenyl)-4-phenylbutan-2-one

Conditions
ConditionsYield
With potassium hydroxide; [{Rh(C2H4)2Cl}2]; (-)-borneol biphenol phosphite In 1,4-dioxane; water at 80℃; for 15h;100%
Rh(dpm)(CO)2; 1,3-bis(2-diphenylphosphinomethylphenyl)benzene In cyclohexane; water at 60℃; for 16h;98%
With potassium phosphate; ferrocenyl-containing palladacycle In toluene at 20℃;93%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; tetrafluoroboric acid; diamminedichloropalladium(II) In water at 80℃; for 24h; pH=1;88%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

(E)-3-methyl-1-phenylhexa-1,5-dien-3-ol
100840-12-8

(E)-3-methyl-1-phenylhexa-1,5-dien-3-ol

Conditions
ConditionsYield
With indium iodide In tetrahydrofuran at 40℃; for 24h;100%
With ethanol; diethylzinc In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;93%
With tricyclohexylphosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran at 65℃; for 12h;
ethyl bromozincacetate;THF

ethyl bromozincacetate;THF

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

ethyl (4E)-3-hydroxy-3-methyl-5-phenylpent-4-enoate

ethyl (4E)-3-hydroxy-3-methyl-5-phenylpent-4-enoate

Conditions
ConditionsYield
Stage #1: ethyl bromozincacetate;THF; (E)-benzalacetone In tetrahydrofuran at 0 - 25℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;
100%
methylamine
74-89-5

methylamine

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

C11H13N
1261161-43-6

C11H13N

Conditions
ConditionsYield
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

ethylhydrazine carboxylate
4114-31-2

ethylhydrazine carboxylate

Benzylideneacetone (ethoxycarbonyl)hydrazone

Benzylideneacetone (ethoxycarbonyl)hydrazone

Conditions
ConditionsYield
With acetic acid In ethanol for 24h; Ambient temperature;99%
(E)-benzalacetone
1896-62-4

(E)-benzalacetone

1-phenyl-3-butanol
2344-70-9

1-phenyl-3-butanol

Conditions
ConditionsYield
(HN(iPr2PC2H4)2)IrH3 In isopropyl alcohol at 25℃; for 1 - 2h; Conversion of starting material;99%
With potassium tert-butylate; IrH2Cl[(iPr2PC2H4)2NH] In isopropyl alcohol at 25℃; for 1 - 2h; Conversion of starting material;99%
With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex; (bis[(2-dicyclohexylphosphino)ethyl]amine)cobalt(II)(CH2SiMe3); isopropyl alcohol In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;98%

1896-62-4Relevant articles and documents

Stereospecific alkyne reduction: Novel activity of old yellow enzymes

Mueller, Andre,Stuermer, Rainer,Hauer, Bernhard,Rosche, Bettina

, p. 3316 - 3318 (2007)

Old enzyme, new trick: An environmentally sustainable alternative for the regio-and stereoselective reduction of the alkyne bond is the biotransformation by "Old Yellow Enzyme" (OYE). This "old" enzyme, first isolated in 1932, catalyzes the trans-selective hydrogenation of the carbon-carbon triple bond under mild conditions. (Chemical Equation Presented).

Tuning the hydrogen donor/acceptor behavior of ionic liquids in Pd-catalyzed multi-step reactions

López-Vinasco, Angela M.,Guerrero-Ríos, Itzel,Favier, Isabelle,Pradel, Christian,Teuma, Emmanuelle,Gómez, Montserrat,Martin, Erika

, p. 56 - 61 (2015)

Palladium nanoparticles stabilized by thioether-phosphine ligands (1-3) were used as catalytic precursors in Heck-Mizoroki cross-coupling and CC reduction reactions in ionic liquids. The ionic liquid [EMI][MeHPO3] (A) exhibited an important hydrogen donor/acceptor behavior depending on the reaction conditions. Tandem or parallel pathways for C-C coupling and H-transfer reactions were observed, leading to the coupled product trans-4-phenyl-3-buten-2-one (I) and the corresponding reduced partner 4-phenylbutan-2-one (II) pointing to a molecular-like catalytic reactivity of the process. When the reaction was carried out under hydrogen pressure and low temperature, the reduction to II was inhibited by the presence of thioether-phosphine ligands.

Metal-Controlled Selective [3+2] Cyclization Reactions of Alkenyl Fischer Carbene Complexes and Allenes

Barluenga, Jose,Vicente, Ruben,Barrio, Pablo,Lopez, Luis A.,Tomas, Miguel

, p. 5974 - 5975 (2004)

Chromium alkenyl Fischer carbene complexes undergo selective [3+2] cyclization reactions to allenes in the presence of nickel(0) or rhodium(I) catalysts. Interestingly, the chemo- and regioselectivity of the process are entirely dependent on the nature of the metal. Copyright

Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes

Chan, Wing-Kei,Wong, Man-Kin,Che, Chi-Ming

, p. 4226 - 4232 (2005)

By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H 2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals.

Stereospecific synthesis of phosphono-(1Z,3E)-dienyl compounds from β-phenyltelluro-vinylphosphonates and -vinylphosphine oxides

Braga, Antonio L.,Rhoden, Cristiano R.B.,Zeni, Gilson,Silveira, Claudio C.,Andrade, Leandro H.

, p. 35 - 40 (2003)

Phosphono-1,3-dienyl compounds 2 can be prepared by palladium cross-coupling reaction of β-phenyltelluro-vinylphosphonates or -vinylphosphine oxides with alkenes in the presence of a catalytic amount of PdCl2 and AcOAg as reoxidant agent at room temperature. The coupling reaction is stereospecific and the compounds 2 were obtained in good yields with total retention of configuration.

Highly dispersed nickel and palladium nanoparticle silica aerogels: Sol-gel processing of tethered metal complexes and application as catalysts in the Mizoroki-Heck reaction

Martinez, Sandra,Moreno-Manas, Marcial,Vallribera, Adelina,Schubert, Ulrich,Roig, Anna,Molins, Elies

, p. 1093 - 1097 (2006)

Highly dispersed Ni and Pd silica aerogels were prepared through sol-gel processes. They have been synthesized by tethering the metal to the silica matrix with the use of the complexing silanes AEAPTS [N-(aminoethyl)aminopropyl] trimethoxysilane or TRIAMIN [N-((aminoethyl)aminoethyl)aminopropyl] trimethoxysilane. The gels were dried with scCO2 to afford the aerogels. High metal dispersion and small particle sizes were observed through HRTEM and XRD measurements. The organic groups were removed by oxidation and/or pyrolysis. The Pd reduced aerogels containing 15-17% of palladium are good recoverable catalysts in the Mizoroki-Heck reaction. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

-

Ksander,McMurry

, p. 4691 (1976)

-

An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones

Pan, Gao-Fei,Wang, Zhe,Chang, Yi-Yuan,Hao, Yue,Wang, Yi-Chen,Xing, Rui-Guang

supporting information, (2021/12/30)

An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.

Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption

Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Mor?o, Luana G.,Sardi, Janaína C.O.,Campos, Débora L.,Silva, Isabel C.,Cavalca, Lúcia B.,Scheffers, Dirk-Jan,Rosalen, Pedro L.,Pavan, Fernando R.,Ferreira, Henrique,Regasini, Luis O.

, (2021/02/22)

Curcumin (CUR) is a symmetrical dicarbonyl compound with antibacterial activity. On the other hand, pharmacokinetic and chemical stability limitations hinder its therapeutic application. Monocarbonyl analogs of curcumin (MACs) have been shown to overcome these barriers. We synthesized and investigated the antibacterial activity of a series of unsymmetrical MACs derived from acetone against Mycobacterium tuberculosis and Gram-negative and Gram-positive species. Phenolic MACs 4, 6 and 8 showed a broad spectrum and potent activity, mainly against M. tuberculosis, Acinetobacter baumannii and methicillin-resistant Staphylococcus aureus (MRSA), with MIC (minimum inhibitory concentration) values ranging from 0.9 to 15.6 μg/mL. The investigation regarding toxicity on human lung cells (MRC-5 and A549 lines) revealed MAC 4 was more selective than MACs 6 and 8, with SI (selectivity index) values ranging from 5.4 to 15.6. In addition, MAC 4 did not demonstrate genotoxic effects on A549 cells and it was more stable than CUR in phosphate buffer (pH 7.4) for 24 h at 37 °C. Fluorescence and phase contrast microscopies indicated that MAC 4 has the ability to disrupt the divisome of Bacillus subtilis without damaging its cytoplasmic membrane. However, biochemical investigations demonstrated that MAC 4 did not affect the GTPase activity of B. subtilis FtsZ, which is the main constituent of the bacterial divisome. These results corroborated that MAC 4 is a promising antitubercular and antibacterial agent.

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

He, Wenfei,Wang, Jingsong,Jin, Qiling,Zhang, Jiafeng,Liu, Yugang,Jin, Zewu,Wang, Hua,Hu, Linya,Zhu, Lu,Shen, Mengya,Huang, Lili,Huang, Shengwei,Li, Wulan,Zhuge, Qichuan,Wu, Jianzhang

, (2021/07/06)

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

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