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189028-95-3

Basic Information
CAS No.: 189028-95-3
Name: (4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one
Article Data: 25
Cas Database
Molecular Structure:
Molecular Structure of 189028-95-3 ((4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one)
Formula: C20H20FNO4
Molecular Weight: 357.382
Synonyms: (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE;
EINECS: 606-165-0
Density: 1.297
Melting Point: N/A
Boiling Point: 572.727 °C at 760 mmHg
Flash Point: 300.174 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 66.84000
LogP: 3.68740
Synthetic route
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With TarB-N02 In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With lithium borohydride In tetrahydrofuran for 0.666667h; Reagent/catalyst; enantioselective reaction;
96%
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 4 - 6h;
Stage #2: With sulfuric acid; dihydrogen peroxide In methanol; dichloromethane; water; toluene for 0.25h;
95%
Stage #1: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 0.25h;
Stage #2: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione In dichloromethane; toluene at -5 - 0℃; for 4 - 6h;
95%
108-05-4

vinyl acetate

1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A

1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Lipozyme TL IM In toluene at 20 - 40℃; Product distribution / selectivity;A 68%
B 74%
With Candida rugosa lipase In di-isopropyl ether at 35℃; for 120h; Solvent; Reagent/catalyst; Concentration; Enzymatic reaction;A n/a
B n/a
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

C

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
With borane-THF; boron trifluoride diethyl etherate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 25℃; Product distribution; Further Variations:; Catalysts; Temperatures; acid additives, water content;
With BH3-DEA; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 40℃;
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
With sodium tetrahydroborate; dimethyl sulfate; N,N-diethylaniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;A 13 g
B n/a
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 18 - 20℃; for 1h;
Stage #2: With water; potassium carbonate In tetrahydrofuran; toluene at 20 - 30℃; for 0.5h;
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 24℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-2-[bis(4-trifluorophenyl)hydroxymethyl]pyrrolidine In tetrahydrofuran at 24℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid/triethylamine complex 5:2 In tert-butyl methyl ether at 42℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; stereoselective reaction;A n/a
B n/a
67-63-0

isopropyl alcohol

189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
With magnesium sulfate In triethanolamine(chloride)

C24H26FNO5

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme

C24H26FNO5

A

1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: triethylamine; dmap / dichloromethane / 4 h / 0 °C
3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme

C24H26FNO5

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme

C24H26FNO5

A

1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: triethylamine; dmap / dichloromethane / 4 h / 0 °C
3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme
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  • cas:189028-95-3

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    cas:189028-95-3

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  • (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

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    189028-95-3

    (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

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Specification

The (4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one , with the CAS register number 189028-95-3, is also known to us as 2-Oxazolidinone,3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-,(4S)- .

The physical properties of this kind of chemical are as following: (1)ACD/BCF (pH 5.5):  12  ; (2)ACD/BCF (pH 7.4):  12  ; (3)ACD/KOC (pH 5.5):  202  ; (4)ACD/KOC (pH 7.4):  202  ; (5)#H bond acceptors:  5 ; (6)#H bond donors:  1  ; (7)#Freely Rotating Bonds:  7  ; (8)Polar Surface Area:  66.84  ; (9)Index of Refraction:  1.588  ; (10)Molar Refractivity:  92.704 cm3  ; (11)Molar Volume:  275.439 cm3  ; (12)Polarizability:  36.751× 10-24 cm3  ; (13)Surface Tension:  53.758 dyne/cm  ; (14)Density:  1.297 g/cm ; (15)Flash Point:  300.174 °C  ; (16)Enthalpy of Vaporization:  90.31 kJ/mol  ; (17)Boiling Point:  572.727 °C at 760 mmHg .

In addition, you could obtain the molecular structure by using the following data information:
SMILES:Fc1ccc(cc1)[C@@H](O)CCCC(=O)N3C(=O)OC[C@@H]3c2ccccc2
InChI:InChI=1/C20H20FNO4/c21-16-11-9-15(10-12-16)18(23)7-4-8-19(24)22-17(13-26-20(22)25)14-5-2-1-3-6-14/h1-3,5-6,9-12,17-18,23H,4,7-8,13H2/t17-,18+/m1/s1
InChIKey:AVAZNWOHQJYCEL-MSOLQXFVBC

As for its market informaiton, you could find many suppliers in China, such as Ningbo Hi-Tech Biochemicals Co., Ltd. and Yancheng Henz Chemical Co., Ltd.