Dimethyl (3-phenoxy-2-oxopropyl)phosphonate supplier

Name
DIMETHYL(3-PHENOXY-2-OXOPROPYL)PHOSPHONATE
EINECS
CAS No. 40665-68-7
Article Data28
CAS DataBase
Density 1.21 g/cm³
Solubility
Melting Point
Formula C₁₁H₁₅O₅P
Boiling Point 369.8 °C at 760 mmHg
Molecular Weight 258.211
Flash Point 191.1 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Phosphonicacid, (2-oxo-3-phenoxypropyl)-, dimethyl ester (9CI);(2-Oxo-3-phenoxypropyl)phosphonic acid dimethyl ester;Dimethyl(2-oxo-3-phenoxypropyl)phosphonate;Dimethyl (3-phenoxyacetonyl)phosphonate;Dimethyl 3-phenoxy-2-oxopropylphosphonate;
PSA 71.64000
LogP 2.12040

Synthetic route

: 2065-23-8
methyl 2-phenoxyacetate

: 756-79-6
dimethyl methane phosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl 2-phenoxyacetate In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere;	83%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: methyl 2-phenoxyacetate In tetrahydrofuran at 25℃;	25%
With n-butyllithium 1.) THF, hexane, -78 deg C, 5 min, 2.) -78 deg C, 2 h; Yield given. Multistep reaction;
With n-butyllithium In tetrahydrofuran; hexane; water

: 2065-23-8
methyl 2-phenoxyacetate

: 34939-91-8, 58648-56-9
dimethyl lithiomethylphosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃;

: 709-84-2
bis-tetrahydropyran-2-yl ether

: 109-72-8, 29786-93-4
n-butyllithium

: 701-99-5
Phenoxyacetyl chloride

: 756-79-6
dimethyl methane phosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
In tetrahydrofuran; hexane; water

...Expand

: 2555-49-9
phenoxyacetic acid ethyl ester

: 756-79-6
dimethyl methane phosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane
With n-butyllithium In tetrahydrofuran; hexane

: 701-99-5
Phenoxyacetyl chloride

: 756-79-6
dimethyl methane phosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
In tetrahydrofuran; hexane
In tetrahydrofuran; hexane

methyl 9α-acetoxy-11α-(2-tetrahydropyranyloxy)-15α-hdroxy-16-phenoxy-17,18,19,20-tetranorprosta-cis-5,trans-13-dienoate: methyl 9α-acetoxy-11α-(2-tetrahydropyranyloxy)-15α-hdroxy-16-phenoxy-17,18,19,20-tetranorprosta-cis-5,trans-13-dienoate

: 2555-49-9
phenoxyacetic acid ethyl ester

: 756-79-6
dimethyl methane phosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane

...Expand

: 108-95-2
phenol

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 16 h / 25 - 56 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2.5 h / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.67 h / 25 °C 1.2: 16 h / 30 - 35 °C 2.1: zinc(II) chloride / toluene / 6 h / 65 - 70 °C / Inert atmosphere 3.1: Jones reagent / acetone / 7 h / Cooling with ice View Scheme

: 122-60-1
Phenyl glycidyl ether

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride / toluene / 6 h / 65 - 70 °C / Inert atmosphere 2: Jones reagent / acetone / 7 h / Cooling with ice View Scheme

: 2-hydroxy-3-phenoxypropyldimethylphosphonate

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions

Conditions	Yield
With Jones reagent In acetone for 7h; Cooling with ice;	92.8 g

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

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

: 51638-91-6
(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Conditions

Conditions	Yield
With sodium hydride Horner-Emmons reaction;	90%
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 25 - 35℃; for 0.416667h; Inert atmosphere; Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran; dichloromethane; mineral oil at 25 - 40℃; for 2.08333h; Inert atmosphere;	61%
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With sodium hydroxide; zinc(II) chloride In tetrahydrofuran at 27℃; Inert atmosphere; Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran at 27℃; for 15h; Inert atmosphere;	50%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: isopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate

: isopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate

Conditions

Conditions	Yield
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With n-butyllithium; tetrabutylammomium bromide In dichloromethane at 20 - 30℃; for 1h; Horner-Wadsworth-Emmons Olefination; Stage #2: isopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate In dichloromethane at 20℃; for 15h; Reagent/catalyst; Solvent; Temperature; Horner-Wadsworth-Emmons Olefination;	85.4%

Yield

Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With n-butyllithium; tetrabutylammomium bromide In dichloromethane at 20 - 30℃; for 1h; Horner-Wadsworth-Emmons Olefination;
Stage #2: isopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate In dichloromethane at 20℃; for 15h; Reagent/catalyst; Solvent; Temperature; Horner-Wadsworth-Emmons Olefination;

85.4%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 38698-56-5, 61659-10-7, 62769-46-4
2α-(6-methoxycarbonylhexyl)-3β-formyloxycyclopent-1-one

: 122437-70-1, 129444-27-5
methyl 9,15-dioxo-16-phenoxy-13-trans-17,18,19,20-tetranorprostenoate

Conditions

Conditions	Yield
With potassium hydroxide In dichloromethane for 1h; Ambient temperature;	68%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

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

: 4-((Z)-7-isopropoxy-7-oxohept-2-enyl)-5-((E)-3-oxo-4-phenoxybut-1-enyl)cyclopentane-1,3-diyl dibenzoate

Conditions

Conditions	Yield
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With sodium hydride In 1,2-dimethoxyethane at -5 - 25℃; for 1.25h; Horner-Wadsworth-Emmons olefination; 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; Horner-Wadsworth-Emmons olefination; Inert atmosphere;	60%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: C21H29NO6S

: isopropyl 2-[(2R,4aR,5R,6R,7aS)-5-[(1E)-3-oxo-4-phenoxy-1-buten-1-yl]-6-(tetrahydro-2H-pyran-2-yloxy)octahydrocyclopenta[b]pyran-2-yl]-1,3-thiazole-4-carboxylate

Conditions

Conditions	Yield
With triethylamine; lithium chloride In tetrahydrofuran at 20℃; for 16h;	52%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 129367-74-4
11-((1S,2R)-2-Formyl-5-oxo-cyclopentyl)-undecanoic acid methyl ester

: 129367-85-7
11-[(1S,5S)-2-Oxo-5-((E)-3-oxo-4-phenoxy-but-1-enyl)-cyclopentyl]-undecanoic acid methyl ester

Conditions

Conditions	Yield
With potassium hydroxide In dichloromethane for 1h; Ambient temperature;	50%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 78845-62-2, 111900-95-9
Biphenyl-4-carboxylic acid (3aS,5S,6aR)-4-formyl-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

: 111803-58-8
Biphenyl-4-carboxylic acid (3aS,5S,6aR)-2-oxo-4-((E)-3-oxo-4-phenoxy-but-1-enyl)-octahydro-cyclopenta[b]pyrrol-5-yl ester

Conditions

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane Ambient temperature; 1.) 0.5 h 2.) 3 h;	19%

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 62961-72-2
Corey aldehyde

: 871669-32-8
7α-hydroxy-6β-(3'-oxo-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 5h; Yield given;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 122517-79-7
7α-trimethylsilyloxy-6β-formyl-2-oxabicyclo<3.3.0>octan-3-one

: 871669-30-6
7α-trimethylsilyloxy-6β-(3'-oxo-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one

Conditions

Conditions	Yield
With potassium hydroxide In dichloromethane for 0.333333h; Ambient temperature; Yield given;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

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

: 87929-54-2
(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

Conditions

Conditions	Yield
With sodium hydride 1.) DME, 2.) 23 deg C; Multistep reaction;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 88736-15-6
2α-(7-methoxycarbonyl-4Z-heptenyl)-3β-formylcyclopentanone

: 131846-19-0
methyl 1-homo-3,4-cis-didehydro-9,15-diketo-16-phenoxy-17,18,19,20-tetranorprostenoate

Conditions

Conditions	Yield
With sodium hydride 1.) THF, RT, 1.5 h, 2.) THF, RT, 30 min; Yield given. Multistep reaction;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 78932-40-8
7-(4-Formyl-furan-3-yl)-heptanoic acid methyl ester

: 7-[4-((E)-3-Oxo-4-phenoxy-but-1-enyl)-furan-3-yl]-heptanoic acid methyl ester

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 61218-06-2
methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

: 62561-47-1
16-phenoxy-17,18,19,20-tetranor-15-dehydroprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

Conditions

Conditions	Yield
With sodium hydride 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h; Yield given. Multistep reaction;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 141242-63-9
C64H110O17Si3

: 141242-73-1
C73H118O18Si3

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile Ambient temperature; Yield given;

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

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

: 79171-99-6
Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions

Conditions	Yield
With sodium hydride 1.) THF, 90 min, 2.) THF, 30 min; Yield given. Multistep reaction;
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate; (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate With water; lithium hydroxide In dichloromethane at 5 - 22℃; for 19.5h; Stage #2: With citric acid In dichloromethane at 22℃; pH=1-2; Reagent/catalyst;	8.7 g

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 51638-93-8, 60761-96-8, 63324-34-5, 103616-92-8, 127760-07-0
7α-hydroxy-6β-(3'-hydroxy-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 871669-32-8
7α-hydroxy-6β-(3'-oxo-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 127718-28-9
7α-trimethylsilyloxy-6β-(3'α-trimethylsilyloxy-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C View Scheme
Multi-step reaction with 5 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C 5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 127702-12-9
7α-trimethylsilyloxy-6β-(3'α-trimethylsilyloxy-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C View Scheme
Multi-step reaction with 4 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 79172-00-2
N-(methanesulfonyl)-16-phenox-ω-tetranor-PGF2α-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min View Scheme
Multi-step reaction with 6 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C 5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min View Scheme
Multi-step reaction with 7 steps 1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min 2: 25 percent / lithium triethylborohydride / tetrahydrofuran / 0.5 h 3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h 4: 95 percent / p-toluenesulfonic acid / CH2Cl2 / 0.5 h 5: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h 6: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h 7: 40 percent / 65percent aq. acetic acid / 14 h View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-((E)-(R)-4-phenoxy-3-trimethylsilanyloxy-but-1-enyl)-3-trimethylsilanyloxy-cyclopentyl]-hept-5-enoyl}-methanesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 6: 90 percent / acetone / 1.5 h / -45 °C 7: CrO3/pyridine / CH2Cl2 View Scheme
Multi-step reaction with 8 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C 5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 7: 90 percent / acetone / 1.5 h / -45 °C 8: CrO3/pyridine / CH2Cl2 View Scheme

Yield

Multi-step reaction with 7 steps
1: K2CO3 / 5 h / 20 °C
2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C
3: 85 percent / pyridine / 2 h / 5 °C
4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C
5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min
6: 90 percent / acetone / 1.5 h / -45 °C
7: CrO3/pyridine / CH2Cl2
View Scheme

Multi-step reaction with 8 steps
1: KOH / CH2Cl2 / 0.33 h / Ambient temperature
2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C
3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C
4: 85 percent / pyridine / 2 h / 5 °C
5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C
6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min
7: 90 percent / acetone / 1.5 h / -45 °C
8: CrO3/pyridine / CH2Cl2
View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 127718-29-0
N-{(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-((E)-(R)-4-phenoxy-3-trimethylsilanyloxy-but-1-enyl)-3-trimethylsilanyloxy-cyclopentyl]-hept-5-enoyl}-methanesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 6: 90 percent / acetone / 1.5 h / -45 °C View Scheme
Multi-step reaction with 7 steps 1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C 5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 7: 90 percent / acetone / 1.5 h / -45 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: K2CO3 / 5 h / 20 °C
2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C
3: 85 percent / pyridine / 2 h / 5 °C
4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C
5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min
6: 90 percent / acetone / 1.5 h / -45 °C
View Scheme

Multi-step reaction with 7 steps
1: KOH / CH2Cl2 / 0.33 h / Ambient temperature
2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C
3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C
4: 85 percent / pyridine / 2 h / 5 °C
5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C
6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min
7: 90 percent / acetone / 1.5 h / -45 °C
View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 209861-01-8
(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 90 percent / NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C 3: potassium carbonate / methanol / 1.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium hydroxide; water / dichloromethane / 19.5 h / 5 - 22 °C 1.2: 22 °C / pH 1-2 2.1: diethylamino-sulfur trifluoride / dichloromethane / 94 h / 5 - 30 °C / Inert atmosphere 3.1: potassium carbonate / methanol / 2 h / 20 °C 3.2: 1 h / 0 °C / Acidic conditions View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 209861-02-9
(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C View Scheme
Multi-step reaction with 4 steps 1: 90 percent / NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride; zinc(II) chloride / mineral oil; tetrahydrofuran / 0.42 h / 25 - 35 °C / Inert atmosphere 1.2: 2.08 h / 25 - 40 °C / Inert atmosphere 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 0 - 35 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 3.25 h / -65 - -61 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C 3: potassium carbonate / methanol / 1.5 h / 20 °C 4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -70 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 209861-00-7
(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybutan-1-en-1-yl)-hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride; zinc(II) chloride / mineral oil; tetrahydrofuran / 0.42 h / 25 - 35 °C / Inert atmosphere 1.2: 2.08 h / 25 - 40 °C / Inert atmosphere 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 0 - 35 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 209860-88-8
AFP-172

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 90 percent / NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride; zinc(II) chloride / mineral oil; tetrahydrofuran / 0.42 h / 25 - 35 °C / Inert atmosphere 1.2: 2.08 h / 25 - 40 °C / Inert atmosphere 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 0 - 35 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 3.25 h / -65 - -61 °C / Inert atmosphere 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 5 °C / Inert atmosphere 4.2: 2 h / 0 - 3 °C View Scheme
Multi-step reaction with 5 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C 3: potassium carbonate / methanol / 1.5 h / 20 °C 4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -70 °C 5: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / 0 - 10 °C View Scheme

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: tafluprost

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 16 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 16 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydride; zinc(II) chloride / mineral oil; tetrahydrofuran / 0.42 h / 25 - 35 °C / Inert atmosphere 1.2: 2.08 h / 25 - 40 °C / Inert atmosphere 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / 0 - 35 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 3.25 h / -65 - -61 °C / Inert atmosphere 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 5 °C / Inert atmosphere 4.2: 2 h / 0 - 3 °C 5.1: acetone / 20 °C 6.1: sulfuric acid / ethyl acetate 6.2: 20 h / 30 °C View Scheme

Dimethyl (3-phenoxy-2-oxopropyl)phosphonate Specification

The Dimethyl (3-phenoxy-2-oxopropyl)phosphonate with the CAS number 40665-68-7 is also called Phosphonic acid,P-(2-oxo-3-phenoxypropyl)-, dimethyl ester. Its systematic name is 1-dimethoxyphosphoryl-3-phenoxypropan-2-one. Its molecular formula is C₁₁H₁₅O₅P.

The properties of the Dimethyl (3-phenoxy-2-oxopropyl)phosphonate are: (1)ACD/LogP: 1.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.07; (4)ACD/LogD (pH 7.4): 1.07; (5)ACD/BCF (pH 5.5): 3.86; (6)ACD/BCF (pH 7.4): 3.86; (7)ACD/KOC (pH 5.5): 91.52; (8)ACD/KOC (pH 7.4): 91.52; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 71.64 Å²; (13)Index of Refraction: 1.491; (14)Molar Refractivity: 61.85 cm³; (15)Molar Volume: 213.4 cm³; (16)Polarizability: 24.52×10^-24cm³; (17)Surface Tension: 40.8 dyne/cm; (18)Enthalpy of Vaporization: 61.66 kJ/mol; (19)Vapour Pressure: 1.16×10^-5 mmHg at 25°C.

Uses: Dimethyl (3-phenoxy-2-oxopropyl)phosphonate can react with 11-(2-formyl-5-oxo-cyclopentyl)-undecanoic acid methyl ester to prepare 11-[2-oxo-5-(3-oxo-4-phenoxy-but-1-enyl)-cyclopentyl]-undecanoic acid methyl ester. This reaction needs reagent KOH and solvent CH₂Cl₂ at Ambient temperature. The reaction time is 1.0 hour. The yield is 50%.

While using Dimethyl (3-phenoxy-2-oxopropyl)phosphonate, you should be very cautious. This chemical is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OC)(OC)CC(=O)COc1ccccc1;
(2)InChI: InChI=1/C11H15O5P/c1-14-17(13,15-2)9-10(12)8-16-11-6-4-3-5-7-11/h3-7H,8-9H2,1-2H3;
(3)InChIKey: NQTSTBMCCAVWOS-UHFFFAOYAM;

Product Name

DIMETHYL(3-PHENOXY-2-OXOPROPYL)PHOSPHONATE

Synthetic route

Dimethyl (3-phenoxy-2-oxopropyl)phosphonate Specification

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