Product Name

  • Name

    Dimethyl (2-oxo-4-phenylbutyl)phosphonate

  • EINECS
  • CAS No. 41162-19-0
  • Article Data40
  • CAS DataBase
  • Density 1.152 g/cm3
  • Solubility
  • Melting Point 120-122 (0.5 MMHG)oC
  • Formula C12H17O4P
  • Boiling Point 362.7 °C at 760 mmHg
  • Molecular Weight 256.238
  • Flash Point 186.8 °C
  • Transport Information
  • Appearance clear yellow liquid
  • Safety 24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 41162-19-0 (Dimethyl (2-oxo-4-phenylbutyl)phosphonate)
  • Hazard Symbols IrritantXi
  • Synonyms Phosphonicacid, (2-oxo-4-phenylbutyl)-, dimethyl ester (9CI);(2-Oxo-4-phenylbutyl)phosphonic acid dimethyl ester;Dimethyl(2-oxo-4-phenylbutyl)phosphonate;
  • PSA 62.41000
  • LogP 2.67420

Synthetic 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%
...Expand
[(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%
...Expand
[(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;

Dimethyl (2-oxo-4-phenylbutyl)phosphonate Chemical Properties

Molecule structure of Phosphonic acid,P-(2-oxo-4-phenylbutyl)-, dimethyl ester (CAS NO.41162-19-0):

IUPAC Name: 1-Dimethoxyphosphoryl-4-phenylbutan-2-one
Molecular Weight: 256.234741 [g/mol]
Molecular Formula: C12H17O4P 
Index of Refraction: 1.494
Molar Refractivity: 64.72 cm3
Molar Volume: 222.2 cm3
Surface Tension: 40.1 dyne/cm
Density: 1.152 g/cm3 
Melting Point: 120-122 °C (0.5 mmHg)
Flash Point: 186.8 °C
Enthalpy of Vaporization: 60.87 kJ/mol
Boiling Point: 362.7 °C at 760 mmHg
Vapour Pressure: 1.9E-05 mmHg at 25 °C
XLogP3-AA: 1.1
H-Bond Acceptor: 4
Rotatable Bond Count: 7
Tautomer Count: 3
Exact Mass: 256.086446
MonoIsotopic Mass: 256.086446
Topological Polar Surface Area: 52.6
Heavy Atom Count: 17
Canonical SMILES: COP(=O)(CC(=O)CCC1=CC=CC=C1)OC
InChI: InChI=1S/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
InChIKey: ONYIBVIIOCEBIV-UHFFFAOYSA-N
Product Categories of Phosphonic acid,P-(2-oxo-4-phenylbutyl)-, dimethyl ester (CAS NO.41162-19-0): Phenyls & Phenyl-Het; Phenyls & Phenyl-Het

Dimethyl (2-oxo-4-phenylbutyl)phosphonate Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.

Dimethyl (2-oxo-4-phenylbutyl)phosphonate Specification

 Phosphonic acid,P-(2-oxo-4-phenylbutyl)-, dimethyl ester (CAS NO.41162-19-0) is also called Dimethyl(2-oxo-4-phenylbutyl)phosphonate .

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