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41162-19-0

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41162-19-0 Usage

Description

Dimethyl (2-oxo-4-phenylbutyl)phosphonate, also known as Bimatoprost Impurity 12, is a chemical compound derived from Bimatoprost, which is an antiglaucoma agent and a synthetic prostamide structurally related to prostaglandin F2α. It is characterized by its clear yellow liquid appearance.

Uses

Used in Pharmaceutical Industry:
Dimethyl (2-oxo-4-phenylbutyl)phosphonate is used as an impurity in the production of Bimatoprost for the treatment of glaucoma. It plays a role in the synthesis process of Bimatoprost, which is a medication that helps to reduce high pressure inside the eye, thereby preventing optic nerve damage and vision loss.
Used in Research and Development:
Dimethyl (2-oxo-4-phenylbutyl)phosphonate is also utilized in research and development for the study of its chemical properties and potential applications in the pharmaceutical field. This includes understanding its interactions with other compounds and its role in the synthesis of related pharmaceuticals.
Used in Quality Control:
In the context of quality control, Dimethyl (2-oxo-4-phenylbutyl)phosphonate is used to ensure the purity and efficacy of Bimatoprost. By monitoring the levels of this impurity, manufacturers can maintain the quality and safety of the final product, which is crucial for the treatment of glaucoma patients.

Check Digit Verification of cas no

The CAS Registry Mumber 41162-19-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,1,6 and 2 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 41162-19:
(7*4)+(6*1)+(5*1)+(4*6)+(3*2)+(2*1)+(1*9)=80
80 % 10 = 0
So 41162-19-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H17O4P/c1-15-17(14,16-2)10-12(13)9-8-11-6-4-3-5-7-11/h3-7H,8-10H2,1-2H3

41162-19-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Dimethyl (2-oxo-4-phenylbutyl)phosphonate

1.2 Other means of identification

Product number -
Other names 1-dimethoxyphosphoryl-4-phenylbutan-2-one

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:41162-19-0 SDS

41162-19-0Synthetic route

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 3-phenylpropanoic acid methyl ester In tetrahydrofuran at -78℃; for 1h;
98%
With n-butyllithium In tetrahydrofuran at -78 - 0℃; Inert atmosphere;98%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 3-phenylpropanoic acid methyl ester In tetrahydrofuran; hexane at -78 - 0℃;
97%
ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran at 5 - 20℃; Inert atmosphere;95%
With n-butyllithium 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min; Multistep reaction;
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane; water; acetic acid
Stage #1: dimethyl methane phosphonate With n-hexyllithium In tetrahydrofuran; hexane at -80℃; Inert atmosphere;
Stage #2: ethyl dihydrocinnamate In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
Stage #3: With water In tetrahydrofuran; hexane at 20℃;
With n-butyllithium In tetrahydrofuran; hexane
argon

argon

1-iodo-4-phenylbutan-2-one
352276-27-8

1-iodo-4-phenylbutan-2-one

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
With phosphorous acid trimethyl ester In acetonitrile85%
1-iodo-4-phenylbutan-2-one
352276-27-8

1-iodo-4-phenylbutan-2-one

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2.5h; Reflux; Inert atmosphere;60%
dimethyl (2-oxopropyl)phosphonate
4202-14-6

dimethyl (2-oxopropyl)phosphonate

benzyl chloride
100-44-7

benzyl chloride

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
(i) NaH, THF, (ii) nBuLi, hexane, (iii) /BRN= 471308/; Multistep reaction;
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: H2 / 5 percent Pd/C / ethyl acetate
2.1: MeOH
3.1: N-BuLi / tetrahydrofuran / 0 °C
3.2: tetrahydrofuran
View Scheme
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: MeOH
2.1: N-BuLi / tetrahydrofuran / 0 °C
2.2: tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid
2: n-butyllithium / tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1.1: sulfuric acid / 2 h / Reflux
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 2 h / Reflux
2: n-butyllithium / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
View Scheme
4-Phenyl-2-butanone
2550-26-7

4-Phenyl-2-butanone

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine / methanol / 2.83 h / -5 - 20 °C / Inert atmosphere
2: sodium iodide / acetone / 6 h / 20 °C / Inert atmosphere
3: acetonitrile / 2.5 h / 20 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: bromine / methanol / 4 h / 0 - 15 °C
2: sodium iodide / acetone / 12 h
3: acetonitrile / 3 h / 65 °C
View Scheme
Multi-step reaction with 2 steps
1: bromine; acetic acid / methanol / Inert atmosphere
2: acetonitrile / 3 h / 65 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: iodine; copper(II) oxide / methanol; dichloromethane / 15 h / 42 °C / Inert atmosphere
2: acetonitrile / 3 h / 65 °C / Inert atmosphere
View Scheme
1-bromo-4-phenylbutan-2-one
31984-10-8

1-bromo-4-phenylbutan-2-one

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide / acetone / 6 h / 20 °C / Inert atmosphere
2: acetonitrile / 2.5 h / 20 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sodium iodide / acetone / 12 h
2: acetonitrile / 3 h / 65 °C
View Scheme
trimethyl phosphite
512-56-1

trimethyl phosphite

1-iodo-4-phenylbutan-2-one
352276-27-8

1-iodo-4-phenylbutan-2-one

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
In acetonitrile at 65℃; for 3h;73 g
In acetonitrile at 65℃; for 3h; Inert atmosphere;
trimethyl phosphite
512-56-1

trimethyl phosphite

1-bromo-4-phenylbutan-2-one
31984-10-8

1-bromo-4-phenylbutan-2-one

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
In acetonitrile at 65℃; for 3h; Inert atmosphere;72 g
4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Cooling with ice
2: zinc(II) chloride / toluene / 4 h / 65 - 70 °C / Inert atmosphere
3: Jones reagent / acetone / 5 h / Cooling with ice
View Scheme
(2-hydroxy-4-phenyl-butyl)-phosphonic acid dimethyl ester

(2-hydroxy-4-phenyl-butyl)-phosphonic acid dimethyl ester

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Conditions
ConditionsYield
With Jones reagent In acetone for 5h; Cooling with ice;15.8 g
(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde
64091-14-1

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
1240483-13-9

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde In tetrahydrofuran; mineral oil at 0℃;
93%
With triethylamine; lithium chloride In acetonitrile for 2h; Inert atmosphere;92%
(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde
64091-14-1

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

C24H34O4Si

C24H34O4Si

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde In tetrahydrofuran; mineral oil at 0℃; for 1.5h;
93%
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With potassium carbonate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde In tetrahydrofuran at -20℃; Reagent/catalyst; Inert atmosphere;
86%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(4E)-1,7-diphenylhept-4-en-3-one
79559-59-4

(4E)-1,7-diphenylhept-4-en-3-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With potassium carbonate In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere;
Stage #2: 3-phenyl-propionaldehyde at 40℃; for 12h;
92%
With potassium hexamethylsilazane Multistep reaction;
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

1,7-diphenyl-4-heptene-3-one
79559-59-4

1,7-diphenyl-4-heptene-3-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With potassium carbonate In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere;
Stage #2: 3-phenyl-propionaldehyde In tetrahydrofuran at 40℃; for 12h;
92%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate
38754-71-1

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
41639-72-9

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With potassium carbonate In isopropyl alcohol at 25℃; for 0.5h; Horner-Wadsworth-Emmons Olefination;
Stage #2: (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate In isopropyl alcohol at 25℃; for 5h; Temperature; Horner-Wadsworth-Emmons Olefination;
91%
With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at -15℃;70%
With sodium hydride 1.) THF, 90 min, 2.) THF, 30 min; Multistep reaction;
With sodium hydroxide In dichloromethane; water at 0 - 5℃; for 1.5h; Product distribution / selectivity;
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Corey aldehyde
62961-72-2

Corey aldehyde

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: Corey aldehyde In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;
88%
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: Corey aldehyde In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere;
(S)-1-(2-oxoethyl)but-3-enyl acrylate

(S)-1-(2-oxoethyl)but-3-enyl acrylate

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(4S,6E)-8-oxo-10-phenyldeca-1,6-dien-4-yl prop-2-enoate

(4S,6E)-8-oxo-10-phenyldeca-1,6-dien-4-yl prop-2-enoate

Conditions
ConditionsYield
With sodium hexamethyldisilazane at 0℃; for 12h; Horner-Wadsworth-Emmons olefination;87%
C8H13NO3
1092078-92-6

C8H13NO3

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

C18H23NO3
1092078-93-7

C18H23NO3

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Horner-Wadsworth-Emmons olefination;
Stage #2: C8H13NO3 In tetrahydrofuran at 20℃; for 1h; Horner-Wadsworth-Emmons olefination;
86%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one
39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

(3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
55076-60-3

(3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at -15℃;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In acetonitrile at -15℃; Wittig Reaction;
84.7%
With triethylamine; lithium chloride In tetrahydrofuran; dichloromethane at 0℃; for 2h; Horner-Wadsworth-Emmons Olefination; Cooling with ice;73%
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hexamethyldisilazane In 1,2-dimethoxyethane Metallation;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In 1,2-dimethoxyethane Condensation;
With n-butyllithium In tetrahydrofuran; hexane; dichloromethane; acetic acid
With triethylamine; lithium chloride In dichloromethane at 0℃; for 2h; Horner-Emmons reaction;
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

(E)-4-oxo-6-phenylhex-2-enoic acid

(E)-4-oxo-6-phenylhex-2-enoic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -20℃; for 2h; Horner-Wadsworth-Emmons Olefination; stereoselective reaction;83%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

2-dibenzylamino-5-oxo-pentanoic acid benzyl ester
850209-99-3

2-dibenzylamino-5-oxo-pentanoic acid benzyl ester

(S,E)-benzyl 2-(dibenzylamino)-7-oxo-9-phenylnon-5-enoate
1379764-51-8

(S,E)-benzyl 2-(dibenzylamino)-7-oxo-9-phenylnon-5-enoate

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at 20℃; Horner-Wadsworth-Emmons olefination; Inert atmosphere;
Stage #2: 2-dibenzylamino-5-oxo-pentanoic acid benzyl ester In acetonitrile at 20℃; Horner-Wadsworth-Emmons olefination; Inert atmosphere;
80%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

ethyl 2-((1R,2S,3R)-3-(dimethyl(phenyl)silyl)-2-formyl-5-oxocyclopentyl)acetate

ethyl 2-((1R,2S,3R)-3-(dimethyl(phenyl)silyl)-2-formyl-5-oxocyclopentyl)acetate

ethyl 2-((1R,2R,3R)-3-(dimethyl(phenyl)silyl)-5-oxo-2-((E)-3-oxo-5-phenylpent-1-en-1-yl)cyclopentyl)acetate

ethyl 2-((1R,2R,3R)-3-(dimethyl(phenyl)silyl)-5-oxo-2-((E)-3-oxo-5-phenylpent-1-en-1-yl)cyclopentyl)acetate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at 20℃; for 6h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;73%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(3aR,4R,5R,6aS)-5-((tert-butyldiphenylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde

(3aR,4R,5R,6aS)-5-((tert-butyldiphenylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde

(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one
1395619-06-3

(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With triethylamine; lithium chloride In tetrahydrofuran at -10℃; for 1.5h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-5-((tert-butyldiphenylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde In tetrahydrofuran at -10℃; for 2.41667h; Inert atmosphere;
72%
C30H34O7

C30H34O7

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

4-[(Z)-7-isopropoxy-7-oxohept-2-enyl]-5-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentane-1,3-diyl dibenzoate

4-[(Z)-7-isopropoxy-7-oxohept-2-enyl]-5-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentane-1,3-diyl dibenzoate

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In 1,2-dimethoxyethane at -5 - 25℃; Inert atmosphere;
Stage #2: C30H34O7 In 1,2-dimethoxyethane at -5 - 25℃; Wittig reaction; Inert atmosphere;
70%
[(S)-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl) acetaldehyde]

[(S)-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl) acetaldehyde]

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

sodium hydride
7646-69-7

sodium hydride

(6R)-(4-oxo-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one

(6R)-(4-oxo-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate; sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: [(S)-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl) acetaldehyde] In tetrahydrofuran; mineral oil at -78℃; for 1h; Inert atmosphere;
66%
[(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde]
163074-98-4

[(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde]

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

C25H26O4

C25H26O4

Conditions
ConditionsYield
With triethylamine; lithium chloride In tetrahydrofuran at -18 - -10℃; for 25h; Horner-Wadsworth-Emmons Olefination;65%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

dimethyl 2-(3-phenylpropanoyl)benzylphosphonate
1170736-73-8

dimethyl 2-(3-phenylpropanoyl)benzylphosphonate

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With cesium fluoride In tetrahydrofuran at 60℃; for 67h; Inert atmosphere;
Stage #2: With silica gel In tetrahydrofuran; ethyl acetate
65%
(Z)-4-formyl-5-(7-isopropoxy-7-oxohept-2-enyl)cyclopentane-1,3-diyl dibenzoate

(Z)-4-formyl-5-(7-isopropoxy-7-oxohept-2-enyl)cyclopentane-1,3-diyl dibenzoate

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

4-[(Z)-7-isopropoxy-7-oxohept-2-enyl]-5-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentane-1,3-diyl dibenzoate

4-[(Z)-7-isopropoxy-7-oxohept-2-enyl]-5-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentane-1,3-diyl dibenzoate

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With sodium hydride In 1,2-dimethoxyethane at -5 - 25℃; for 1.25h; Wittig reaction; Inert atmosphere;
Stage #2: (Z)-4-formyl-5-(7-isopropoxy-7-oxohept-2-enyl)cyclopentane-1,3-diyl dibenzoate In 1,2-dimethoxyethane at -5 - 25℃; for 2h; Wittig reaction; Inert atmosphere;
65%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(1-diazo-2-oxo-4-phenylbutyl)phosphonic acid dimethyl ester.

(1-diazo-2-oxo-4-phenylbutyl)phosphonic acid dimethyl ester.

Conditions
ConditionsYield
With 4-toluenesulfonyl azide; potassium carbonate63%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one
128948-10-7

(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one

C24H34O4Si

C24H34O4Si

Conditions
ConditionsYield
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With triethylamine; lithium chloride In tetrahydrofuran at -15 - -5℃;
Stage #2: (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one In tetrahydrofuran for 1h;
51%
Stage #1: dimethyl(2-oxo-4-phenylbutyl)phosphonate With lithium hydroxide monohydrate In tert-butyl methyl ether at 20℃; for 1h;
Stage #2: (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one In tert-butyl methyl ether; water at 5℃; for 0.916667h; Wittig-Horner Reaction;
27.5 g
With lithium hydroxide monohydrate In tert-butyl methyl ether at 5℃; for 0.75h; Wittig-Horner Reaction; Inert atmosphere;
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

A

(E)-6,6,6-trifluoro-1,5-diphenylhex-4-en-3-one

(E)-6,6,6-trifluoro-1,5-diphenylhex-4-en-3-one

B

(Z)-6,6,6-trifluoro-1,5-diphenylhex-4-en-3-one

(Z)-6,6,6-trifluoro-1,5-diphenylhex-4-en-3-one

Conditions
ConditionsYield
Stage #1: ethyl trifluoroacetate,; phenylmagnesium bromide In diethyl ether; water at -80 - 0℃; for 2h; Inert atmosphere;
Stage #2: dimethyl(2-oxo-4-phenylbutyl)phosphonate With triethylamine; lithium bromide In tetrahydrofuran; diethyl ether; water at 0 - 40℃; for 5.16h; Inert atmosphere;
A 51%
B 4%
[(S)-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl) acetaldehyde]

[(S)-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl) acetaldehyde]

dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(6R)-(4-oxo-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one

(6R)-(4-oxo-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Horner-Wadsworth-Emmons reaction;20%
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
104596-33-0

methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-5-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-5-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

Conditions
ConditionsYield
With sodium hydride 1.) DME, 2.) 23 deg C; Multistep reaction;
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

<1α,2β(5Z),3β,4α>-7-<5,6-exo-epoxy-3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid methyl ester

<1α,2β(5Z),3β,4α>-7-<5,6-exo-epoxy-3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid methyl ester

(Z)-7-[(1S,2S,4R,5R,6R,7S)-7-((E)-3-Oxo-5-phenyl-pent-1-enyl)-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-yl]-hept-5-enoic acid methyl ester

(Z)-7-[(1S,2S,4R,5R,6R,7S)-7-((E)-3-Oxo-5-phenyl-pent-1-enyl)-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-yl]-hept-5-enoic acid methyl ester

Conditions
ConditionsYield
With triethylamine; lithium bromide 1.) CH2Cl2, 25 deg C, 15 min, 2.) 25 deg C, overnight; Multistep reaction;
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester
177616-22-7

(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-77-7

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
With aluminium trichloride; 3 A molecular sieve; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; phenylboronic acid Yield given. Multistep reaction;

41162-19-0Downstream Products

41162-19-0Relevant articles and documents

Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

Sivák, Ivan,Toběrny, Michal,Kyselicová, Andrea,Caletková, Ol'Ga,Berke?, Du?an,Jakubec, Pavol,Kolarovi?, Andrej

, p. 15541 - 15548 (2018)

Crystallization-induced diastereomer transformation (CIDT) represents a highly appealing and convenient synthetic tool. Despite its numerous advantages, it remains rather rarely used due to its uncertain predictability to occur. Herein, we describe CIDT based on aza-Michael reactions of diversely functionalized (E)-3-acylacrylic acids. This method provides direct access to a broad variety of α-amino acid derivatives in excellent stereochemical purities.

Unsaturated ketone compound as well as preparation method and application thereof

-

, (2020/10/30)

The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.

A new synthetic approach to prostaglandin analogues: Synthesis of bimatoprost via lipase enzymatic catalysis

Kamidi, Vijendhar,Kale, Pooja,Boodida, Sathyanarayana

, p. 2767 - 2770 (2017/11/10)

A simple, convenient and efficient synthetic approach for the synthesis of (15S) bimatoprost (4) via lipase enzyme mediated stereo selective reduction from chiral precursor Corey lactone diol as substrate was described. Swern oxidation, lipase enzymatic reduction and Wittig reaction conditions are used as key steps for the synthesis of bimatoprost. This method was found to be an efficient with considerable yield, cost effective and minimized the synthetic steps compared to reported procedures.

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