168297-85-6

Basic information

• Product Name: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone
• Synonyms: (S)-(-)-4-BENZYL-5,5-DIMETHYL-2-OXAZOLIDINONE;(S)-(+)-4-BENZYL-5,5-DIMETHYL-2-OXAZOLIDINONE;(S)-4-BENZYL-5,5-DIMETHYL-OXAZOLIDIN-2-ONE;(S)-(-)-4-BENZYL-5,5-DIMETHYL-2-OXA- ZOLIDINONE, 98% (99% EE/HPLC);2-Oxazolidinone,5,5-dimethyl-4-(phenylmethyl)-,(4S)-(9CI);(S)-4-Benzyl-5,5-dimethyl-2-oxazolidinone,99%e.e.
• CAS NO: 168297-85-6
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• Product Categories: N-BOC;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 168297-85-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 65-68 °C(lit.)
• Boiling Point: 385ºC at 760 mmHg
• Flash Point: 186.7ºC
• Appearance: /
• Density: 1.085 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.519
• PKA: 12.86±0.60(Predicted)
• CAS DataBase Reference: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(168297-85-6)
• EPA Substance Registry System: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(168297-85-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 168297-85-6(Hazardous Substances Data)

Usage

General Description

(S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is a chemical compound that belongs to the oxazolidinone family. It is a chiral molecule, meaning it has a non-superimposable mirror image, and it is commonly used as a chiral auxiliary in asymmetric synthesis. (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone can be used to control the stereochemistry of reactions, making it a valuable tool in organic chemistry. It is known for its ability to facilitate the formation of new carbon-carbon and carbon-heteroatom bonds, making it important in the development of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and chiral nature make it a versatile and important compound for chemical synthesis and drug development.

InChI:InChI=1/C12H15NO2/c1-12(2)10(13-11(14)15-12)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,13,14)/t10-/m0/s1

Upstream product

• 1169842-90-3 (S)-4-benzyl-3-((2S,3S)-3-hydroxy-2-methyl-4-methylenehexanoyl)-5,5-dimethyloxazolidin-2-one 
• 168297-81-2 N-<(S)-1-benzyl-2-hydroxy-2-methylpropyl>-2,2,2-trichloroethanamide 
• 530-62-1 1,1'-carbonyldiimidazole 
• 63-91-2 L-phenylalanine 
• 75-16-1 methylmagnesium bromide 
• 75-36-5 acetyl chloride 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 1527484-91-8 C₁₈H₂₅NO₄ 
• 1527484-89-4 C₂₂H₂₅NO₅ 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 1373038-24-4 C₂₁H₂₄F₇NO₃ 
• 1373037-98-9 C₂₁H₂₆F₃NO₃ 
• 1373037-72-9 (S)-4-benzyl-3-(2-cyclohexylacetyl)-5,5-dimethyloxazolidin-2-one 
• 1207362-36-4 (S)-4-benzyl-3-hexanoyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 250280-59-2 (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one 
• 320606-12-0 (S)-4-benzyl-N-butanoyl-5,5-dimethyl-1,3-oxazolidin-2-one 
• 618436-90-1 (S)-3-((E)-but-2-enoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 168297-89-0 (S)-3-(2',2'-dimethyl-1'-oxopropyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 1190324-37-8 (S)-4-benzyl-3-(2-chloroacetyl)-5,5-dimethyloxazolidin-2-one 
• 234768-80-0 4S-benzyl-3-(2-butyl-acryloyl)-5,5-dimethyl-oxazolidin-2-one 
• 1169843-03-1 (3S,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3,5-dimethyl-dihydrofuran-2(3H)-one 
• 1169842-90-3 (S)-4-benzyl-3-((2S,3S)-3-hydroxy-2-methyl-4-methylenehexanoyl)-5,5-dimethyloxazolidin-2-one 
• 1169842-97-0 (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-2,4-dimethylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one 
• 1350524-13-8 (S)-4-benzyl-3-((2S,3S)-3-hydroxy-4-methyl-2-phenylpent-4-enoyl)-5,5-dimethyloxazolidin-2-one 

Relevant articles and documents

Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.

Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives

The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction (IMSNAr) of a linear tripeptide to construct a 14-membered paracyclophane ring, resulting in confirmation of its structure and absolute configuration. The structure-activity relationship study of 1 and its derivatives demonstrated that some derivatives possessed cytotoxicity toward human cancer cell lines A549, HT29, and HCT116.

Stereoselective aminoxylation of biradical titanium enolates with TEMPO

A highly efficient and straightforward aminoxylation of titanium(IV) enolates from (S)-N-acyl-4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-ones with TEMPO has been developed. A wide array of functional groups on the acyl moiety, including alkyl and aryl substituents, olefins, esters, or α-cyclopropyl, as well as α-trifluoromethyl groups, are well tolerated. This transformation can therefore produce the α-aminoxylated adducts in excellent yields with high diastereomeric ratios (d.r.). In turn, parallel additions to the α,β-unsaturated N-acyl counterparts give the corresponding γ-adducts with complete regioselectivity in moderate to good yields. Removal of the piperidinyl moiety or the chiral auxiliary converts the resultant adducts into enantiomerically pure α-hydroxy carboxyl derivatives, alcohols, or esters in high yields under mild conditions. Finally, a new mechanistic model based on the biradical character of the titanium(IV) enolates has been proposed.