168297-84-5

Basic information

• Product Name: (S)-Phenyl superquat
• Synonyms: (S)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE;(S)-(+)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE;(S)-PHENYL SUPERQUAT;(S)-(+)-5,5-DIMETHYL-4-PHENYL-2-OXAZOL-I DINONE, 98% (99% EE/HPLC);2-Oxazolidinone,5,5-dimethyl-4-phenyl-,(4S)-(9CI);(S)-5,5-Dimethyl-4-phenyloxazolidin-2-one;(S)-Phenyl superquat,98%;(S)-(+)-5,5-DiMethyl-4-phenyl-2-oxazolidinone
• CAS NO: 168297-84-5
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• Product Categories: N-BOC;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 168297-84-5.mol

Chemical Properties

• Melting Point: 151-156 °C(lit.)
• Boiling Point: 326.97°C (rough estimate)
• Flash Point: 185.6ºC
• Appearance: /
• Density: 1.1258 (rough estimate)
• Vapor Pressure: 4.47E-06mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (S)-Phenyl superquat(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Phenyl superquat(168297-84-5)
• EPA Substance Registry System: (S)-Phenyl superquat(168297-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 168297-84-5(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C11H13NO2/c1-11(2)9(12-10(13)14-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3,(H,12,13)/t9-/m0/s1

Upstream product

• 723263-00-1 (S)-(2-hydroxy-2-methyl-1-phenylpropyl)carbamic acid tert-butyl ester 
• 204851-68-3 (R)-3-Hydroxy-3-methyl-2-phenyl-butyric acid 
• 110-60-1 1,4-diaminobutane 
• 224430-59-5 (3'S,4S)-3-(3'-methyl-1'-oxodecyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-93-3 (4S,1'R,2'S)-N⁽³⁾-[1'-(m-chlorobenzoyl)-2'-hydroxy-2'-phenyl-ethan-1'-yl]-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-97-7 (4S,1'R,2'S)-N⁽³⁾-(1'-m-chlorobenzoyl-2'-hydroxy-3'-phenyl-prop-1'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 848152-34-1 (4S,αS)-3-α-methylbenzyl-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 33664-93-6 5,5-dimethyl-4-phenyl-oxazolidin-2-one 
• 97-72-3 2-Methylpropionic anhydride 
• 169512-94-1 (+/-)-N-tert-butoxycarbonyl-α-phenylglycine methyl ester 
• 6298-96-0 (S)-1-(4-methoxyphenyl)ethylamine 
• 168297-96-9 (S)-3-(3'-phenylpropionyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-91-1 (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 636580-92-2 (4S,2'R,3'S)-N⁽³⁾-(3'-phenyloxiran-2'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 224430-57-3 (4S)-3-<2'(E)-butenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-94-4 (S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-96-6 (S,E)-N⁽³⁾-(3',3'-dimethyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 636580-91-1 (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 636580-95-5 (S,E)-N⁽³⁾-(3'-methyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-83-7 (S)-3-(hepta-2',6'-dienoyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-73-5 (4S,2'E)-3-(3'-phenylacryloyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 168297-96-9 (S)-3-(3'-phenylpropionyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-76-8 (3'S,4S)-4-phenyl-3-(3'-phenylbutyryl)-5,5-dimethyloxazolidin-2-one 
• 637330-80-4 (3'R,4S)-3-(3'-phenylbutyryl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-78-0 (3'R,4S)-3-(4'-methyl-3'-phenylpentanoyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-77-9 (3'S,4S)-3-(3'-phenylhex-5-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-84-8 (3'R,4S)-3-(3-isopropenylhept-6-enoyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-79-1 (3'S,4S)-3-(3',4'-diphenylbutyryl)-4-phenyl-5,5-dimethyloxazolidin-2-one 

Relevant articles and documents

Stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one

A stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one, SuperQuat [(S)-1], is described. The key step is the diastereoselective reduction of (E)-imine (2), which is synthesized from 2-hydroxy-2-methylpropiophenone (4) and (S)-

HYDROXAMIC ACID DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS

The invention relates to a compound of formula (I): or a pharmaceutically acceptable salt thereof, thereof, wherein: G is a group of formula (II); and pharmaceutically acceptable salts, prodrugs, hydrates, or solvates, thereof, wherein A, B. L1-L4 A, B, R1-R4 and m are as defined herein. The invention also relates to pharmaceutical compositions comprising the compounds of formula (I) and their use in treating a bacterial infection.

Stereoselective functionalisation of SuperQuat enamides: asymmetric synthesis of homochiral 1,2-diols and α-benzyloxy carbonyl compounds

Homochiral (E)- and (Z)-enamides derived from SuperQuat (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane. Subsequent epoxide opening with meta-chlorobenzoic acid proceeds via a stereoselective SN1-type process, with retention of configuration, to give the corresponding 1′-m-chlorobenzoyl-2′-hydroxy derivatives. Treatment of the SuperQuat enamides with mCPBA effects this two-step transformation in one pot. Reductive cleavage of the isolated 1′-m-chlorobenzoyl-2′-hydroxy derivatives (≥96% de) generates homochiral 1,2-diols in ≥96% ee. Alternatively, regioselective lithiation of the enamide at C(1′) with tBuLi followed by reaction with an aromatic aldehyde and in situ O-benzylation generates a 1′-(benzyloxy-aryl-methyl) substituted enamide with high diastereoselectivity. Subsequent oxidative cleavage of the enamide C{double bond, long}C bond with NaIO4/RuCl3 followed by methanolysis of the resultant N-acyl fragment furnishes an O-benzyl protected α-hydroxy methyl ester in high ee.

Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation

Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright

Oxidative functionalisation of superquat enamides: Asymmetric synthesis of homochiral 1,2 diols

Homochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ SN1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive cleavage of the isolated 1′-acyloxy-2′-hydroxy derivatives generates 1,2-diols in high yields and in high ee.

SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes

The proclivity of α-branched N-2′-benzyl-3′-phenylpropionyl derivatives of (S)-4-benzyl-5,5-dimethyl-, (S)-4-phenyl-5,5-dimethyl-, (S)-4-isopropyl-5,5-dimethyl-, (S)-4-benzyl- and (S)-4-benzyl-5,5-diphenyl-oxazolidin-2-ones to generate directly 2-benzyl-3-phenylpropionaldehyde upon hydride reduction with DIBAL is investigated. The (S)-4-benzyl-5,5-dimethyl-derivative proved optimal for inhibition of endocyclic nucleophilic attack, giving 2-benzyl-3-phenylpropionaldehyde in good yield upon reduction. Application of this methodology for the asymmetric synthesis of chiral aldehydes via diastereoselective enolate alkylation of a range of (S)-N-acyl-4-benzyl-5,5-dimethyloxazolidin-2-ones to afford an array of α-substituted-N-acyl-5,5-dimethyloxazolidin-2-ones (85-94% de) and subsequent reduction with DIBAL afforded directly non-racemic α-substituted aldehydes without loss of stereochemical integrity (87-94% ee). The extension of this protocol for the asymmetric synthesis of β-substituted aldehydes is demonstrated, via the diastereoselective conjugate addition of a range of organocuprates to (S)-N-acyl-4-phenyl-5,5-dimethyloxazolidin-2-ones which proceeds with high diastereoselectivity (generally >95% de). Reduction of the conjugate addition products with DIBAL gives non-racemic β-substituted aldehydes in high yields and in high ee (generally >95% ee). This methodology is exemplified by the asymmetric synthesis of (R)-3-isopropenylhept-6-enal, which has previously been used in the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromones of the California red scale.

The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B.

(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D- phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (-)-Aplysillamide B.

A practical procedure for the multigram synthesis of the SuperQuat chiral auxiliaries

An efficient and simple synthesis of oxazolidin-2-one SuperQuat chiral auxiliaries is described which provides rapid access to multigram quantities of the auxiliaries.

4-Substituted-5,5-Dimethyl Oxazolidin-2-ones as Effective Chiral Auxiliaries for Enolate Alkylations and Michael Additions

4-(Methyl, phenyl, benzyl, and i-propyl)-5,5-dimethyl-oxazolidin-2-ones, readily available from α-amino acids, are shown to be effective chiral auxiliaries for stereoselective enolate alkylations and conjugate additions of attached N-acyl moieties.