184346-45-0

Basic information

• Product Name: (S)-(-)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE
• Synonyms: (S)-(-)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE;5,5-DIPHENYL-4-ISOPROPYLOXAZOLIDINE-2-ONE;(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one;(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one;(S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone, ee: 99%;(S)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone,99%e.e.;(S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone, 98%, ee: 99%;(4S)-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS NO: 184346-45-0
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.35
• Product Categories: Intermediates of Sertraline;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 184346-45-0.mol

Chemical Properties

• Melting Point: 252-255 °C(lit.)
• Boiling Point: 475.684 °C at 760 mmHg
• Flash Point: 241.486 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.74±0.60(Predicted)
• CAS DataBase Reference: (S)-(-)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(184346-45-0)
• EPA Substance Registry System: (S)-(-)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(184346-45-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 184346-45-0(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white crystal to power solid

InChI:InChI=1/C18H19NO2/c1-13(2)16-18(21-17(20)19-16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-13,16H,1-2H3,(H,19,20)/t16-/m0/s1

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 78603-95-9 1,1-diphenyl-L-valinol 
• 213887-92-4 (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one 
• 213887-88-8 (S)-4-(1-methylethyl)-3-<(S)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one 
• 100-51-6 benzyl alcohol 
• 13734-41-3 t-Boc-L-valine 
• 108-86-1 bromobenzene 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 67-56-1 methanol 
• 916830-67-6 (S)-4-isopropyl-3-[(S)-4-nitro-3-(2-trifluoromethylphenyl)butyryl]-5,5-diphenyloxazolidin-2-one 
• 124-41-4 sodium methylate 
• 100-39-0 benzyl bromide 
• 100-58-3 phenylmagnesium bromide 
• 213887-84-4 (S)-4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyloxazolidin-2-one 

Downstream Products

• 218800-38-5 (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one 
• 218800-35-2 (S)-4-(1-methylethyl)-3-<(E)-2-oxobut-2-enyl>-5,5-diphenyloxazolidin-2-one 
• 218800-36-3 (S)-4-(1-methylethyl)-3-<(E)-1-oxo-3-phenylprop-2-enyl>-5,5-diphenyloxazolidin-2-one 
• 218800-34-1 (S)-4-(1-methylethyl)-3-(3-methyl-1-oxobutyl)-5,5-diphenyloxazolidin-2-one 
• 345904-70-3 (S)-4-isopropyl-5,5-diphenyl-3-phenylsulfanylmethyl-oxazolidin-2-one 
• 464201-36-3 (S)-4-(1-methylethyl)-5,5-diphenyl-3-[(E)-3-phenylprop-2-enyl]oxazolidin-2-one 
• 468721-46-2 (S)-3-(3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 921937-48-6 (S)-3-[(E)-3-(diethoxyphosphinoyl)prop-2-enoyl]-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one 
• 944472-89-3 (4S)-3-(2-bromopropanoyl)-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one 
• 1032199-08-8 (S)-4-isopropyl-5,5-diphenyl-3-[(E)-3-(2-trifluoromethylphenyl)-acryloyl]-oxazolidin-2-one 
• 878194-06-0 (R)-pentafluorophenyl 2-phenylpropionate 
• 1257306-43-6 C₂₇H₂₇NO₃ 
• 345904-96-3 N-[(1S,2S)-2-((S)-4-isopropyl-2-oxo-5,5-diphenyl-oxazolidin-3-yl)-2-methylsulfanyl-1-phenyl-ethyl]-2,4,6-trimethylbenzenesulfonamide 

Relevant articles and documents

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PROCESS FOR THE PREPARATION OF A FLUOROLACTON DERIVATIVE

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METHOD FOR PRODUCING PYRROLIDINE COMPOUND

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Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents

The Ni(acac)2 catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of

Conjugate addition of lithiated (S)-4-isopropyl-3-[(methylthio)methyl]-5,5-diphenyloxazolidin-2-one to cinnamoyl derivatives: Preparation of enantiomerically pure 1,4-diols

The Li derivative of (S)-4-isopropyl-3-[(methylthlio)methyl]-5,5-diphenyloxazolidin-2-one (Li-2; synthetically equivalent to a chiral formyl anion) adds to enones and enoates in a 1,4-fashion. Best results are obtained with 1,3-diarylpropenones (chalcones

Highly effective and recyclable chiral auxiliaries: A study of the synthesis and use of three 4-isopropyl-5,5-diaryloxazolidin-2-ones

A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been synthesised. Studies on the benzylation of the lithium enolates of N-acyl derivatives reveal that the yields obtained were sensitive to the method of quenching the reaction. This was particularly acute for the 5,5-diphenyl system where effective yields (69%) and high diastereoselectivities (dr 98 : 2) are only observed when the reactions were quenched into aqueous buffer. Methylation studies on the N-acyl derivatives showed that the most advantageous results (58-69%, dr ≥ 91 : 9) were only observed using the sodium enolates. The 5,5-ditolyl-4-isopropyloxazolidin-2-one proved to be more efficacious in terms of efficiency and diastereoselectivity (dr ≥ 97 : 3). Subsequent, simple alkaline hydrolyses of the alkylation products allowed for the high recovery and recyclability of the 5,5-diaryl substituted oxazolidin-2-ones without any deleterious endocyclic cleavage. In addition, the acyl portions were recovered in high yield from the alkaline hydrolyses without any evidence of racemisation.

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