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190595-65-4

Basic Information
CAS No.: 190595-65-4
Name: (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Article Data: 28
Cas Database
Molecular Structure:
Molecular Structure of 190595-65-4 ((3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one)
Formula: C31H25F2NO3
Molecular Weight: 497.541
Synonyms: Ezetimibe Intermediates
EINECS: 1308068-626-2
Density: 1.264 g/cm3
Melting Point: N/A
Boiling Point: 706.794 °C at 760 mmHg
Flash Point: 381.255 °C
Solubility: N/A
Appearance: WHITE
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 46.61000
LogP: 6.97600
Synthetic route
954109-22-9

(3R,4S)-4-(4-benzyloxyphenyl)-1-(4-fluoro phenyl)-3-{2-[2-(4-fluorophenyl)-[1,3]-dioxolan-2-yl]ethyl}azetidin-2-one

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid In acetone at 20℃; for 6h; Product distribution / selectivity; Reflux;99%

(S)-ethyl 2-((4-(benzyloxy)phenyl)(4-fluorophenylamino)methyl)-5-(4-fluorophenyl)-5-oxopentanoate

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
at 20℃; for 0.166667h; Temperature;91.6%
953805-24-8

(3R,4S)-4-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-3-{2-[2-(4-fluorophenyl)-5,5-dimethyl-[1,3]dioxan-2-yl]-ethyl}azetidin-2-one

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With formic acid In dichloromethane for 12h; Reflux;90%
With sulfuric acid In water; isopropyl alcohol at 20 - 25℃; for 1h; Product distribution / selectivity;87.9%
With acetic acid at 20 - 25℃; for 1h; Product distribution / selectivity;85.3%
190595-64-3

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl)allyl)azetidin-2-one

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With perchloric acid; palladium diacetate; p-benzoquinone In water; acetonitrile for 16h;90%
942485-56-5

(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In toluene at 60℃;88.94%
1206694-77-0

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(Z)-3-(4-fluorophenyl)allyl]azetidin-2-one

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With perchloric acid; p-benzoquinone; palladium diacetate In water; acetonitrile for 48h; Inert atmosphere;86%
With perchloric acid; water; palladium diacetate; p-benzoquinone In acetonitrile Wacker-Tsuji oxidation; Inert atmosphere;86%

C33H31F2NO4

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.666667h;77%
With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.666667h;77%
934245-14-4

3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide

352-13-6

4-flourophenylmagnesium bromide

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 30 - 32℃; for 2.5h; Solvent; Temperature;75.7%
221349-60-6

(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With Wilkinson's catalyst; hydrogen In dichloromethane under 3102.89 Torr; for 18h; Hydrogenation;71%
352-13-6

4-flourophenylmagnesium bromide

204589-84-4

3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
Stage #1: 4-flourophenylmagnesium bromide With zinc(II) chloride In tetrahydrofuran at 4℃;
Stage #2: 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0℃; for 4.5h;
37%
With zinc(II) chloride; palladium diacetate In toluene at 0 - 20℃; for 2h;
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  • (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

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    (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

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    (3R,4S)-4-[4-(BENZYLOXY)PHENYL]-1-(4-FLUOROPHENYL)-3-[3-(4-FLUOROPHENYL)-3-OXOPROPYL]AZETIDIN-2-ONE

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Specification

The (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one , with the CAS register number 190595-65-4, has other names as E6:synthesis of trans-1-(4-fluorophenyl)-3-[3-oxo-3-(4-fluorophenyl)propyl .

The physical properties of this kind of chemical are as the following: (1)ACD/BCF (pH 5.5):  25455  ; (2)ACD/BCF (pH 7.4):  25455  ; (3)ACD/KOC (pH 5.5):  49573  ; (4)ACD/KOC (pH 7.4):  49573  ; (5)#H bond acceptors:  4  ; (6)#Freely Rotating Bonds:  9  ; (7)Polar Surface Area:  46.61  ; (8)Index of Refraction:  1.61  ; (9)Molar Refractivity:  136.5 cm3  ; (10)Molar Volume:  393.523 cm ; (11)Polarizability:  54.113×10-24 cm ; (12)Surface Tension:  49.155 dyne/cm  ; (13)Density:  1.264 g/cm3  ; (14)Flash Point:  381.255 °C  ; (15)Enthalpy of Vaporization:  103.394 kJ/mol  ; (16)Boiling Point:  706.794 °C at 760 mmHg.

This is a kind of white crystal and it is widely used in the pharmaceutic intermediates. And  its product category are various, for example, the ezetimibe intermediates.

In addition, you could refer to the following data to get the molecular structure:
SMILES:c1ccc(cc1)COc2ccc(cc2)C3C(C(=O)N3c4ccc(cc4)F)CCC(=O)c5ccc(cc5)F
InChI:InChI=1/C31H25F2NO3/c32-24-10-6-22(7-11-24)29(35)19-18-28-30(34(31(28)36)26-14-12-25(33)13-15-26)23-8-16-27(17-9-23)37-20-21-4-2-1-3-5-21/h1-17,28,30H,18-20H2/t28-,30-/m1/s1 
InChIKey:BVYNXBNCXPJQCW-PQHLKRTFBD

As for its market information, there are many suppliers in China, such as Ningbo Hi-Tech Biochemicals Co., Ltd. and Yancheng Henz Chemical Co., Ltd.