170918-42-0

Basic information

• Product Name: (R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE
• Synonyms: (R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE;(R)-PHENYL SUPERQUAT;(R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOL-I DINONE, 98% (99% EE/HPLC);2-Oxazolidinone,5,5-dimethyl-4-phenyl-,(4R)-(9CI);(R)-5,5-Dimethyl-4-phenyloxazolidin-2-one;(R)-Phenyl superquat,98%;(4R)-5,5-Dimethyl-4-phenyl-1,3-oxazolidin-2-one;(R)-(-)-5,5-Dimethyl-4-phenyl-2-oxazolidinone≥ 99.5% (HPLC, Chiral purity)
• CAS NO: 170918-42-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• Product Categories: N-BOC
• Mol File: 170918-42-0.mol

Chemical Properties

• Melting Point: 151-156 °C(lit.)
• Boiling Point: 326.97°C (rough estimate)
• Flash Point: 185.6°C
• 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: (R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE(170918-42-0)
• EPA Substance Registry System: (R)-(-)-5,5-DIMETHYL-4-PHENYL-2-OXAZOLIDINONE(170918-42-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 170918-42-0(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-/m1/s1

Upstream product

• 204851-68-3 (R)-3-Hydroxy-3-methyl-2-phenyl-butyric acid 
• 223906-33-0 ((R)-2-hydroxy-2-methyl-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 110480-87-0 (R)-1-amino-2-methyl-1-phenyl-propan-2-ol 
• 168298-09-7 (3'S,4R)-3-(1'-oxobutyl-3'-phenyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 170918-35-1 N-<(1R)-2-hydroxy-2-methyl-1-phenylpropyl>-2,2,2-trichloroethanamide 
• 170918-36-2 (R)-3-(2',2'-dimethyl-1'-oxopropyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 875-74-1 (R)-phenylglycine 
• 33664-93-6 5,5-dimethyl-4-phenyl-oxazolidin-2-one 
• 1468-39-9 Isovaleric anhydride 
• 141190-94-5 (R)-N-(tert-butoxycarbonyl)phenylglycine methyl ester 
• 168298-07-5 (4R)-3-<2'(E)-butenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 

Downstream Products

• 170918-37-3 (4R)-N-Propionyl-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 170918-36-2 (R)-3-(2',2'-dimethyl-1'-oxopropyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 168298-07-5 (4R)-3-<2'(E)-butenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 762245-32-9 (R)-3-(2-chloroacetyl)-5,5-dimethyl-4-phenyl-oxazolidin-2-one 
• 1059153-44-4 C₁₆H₂₁NO₃ 
• 168298-08-6 (4R)-3-<3'-phenyl-2'(E)-propenoyl>-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 1267475-06-8 diethyl {2-[(4R)-4-Phenyl-2-oxo-1,3-oxazolidin-3-yl]-2-oxoethyl}-phosphonate 
• 1267475-17-1 (R)-3-((R)-3-(3-((E)-3-hydroxyprop-1-en-1-yl)phenyl)hept-6-ynoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 1267475-15-9 (R)-3-((R)-3-(3-((E)-3-((tert-butyldimethylsilyl)oxy)prop-1-en-1-yl)phenyl)-7-(trimethylsilyl)hept-6-ynoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 1267475-14-8 C₂₉H₃₇NO₄Si 
• 1267475-12-6 (4R)-3-((E)-3-(3-(1-hydroxyallyl)phenyl)acryloyl)-5,5-dimethyl-4-phenyloxazolidin-2-one 
• 1267475-10-4 (R,E)-3-(3-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-3-oxoprop-1-en-1-yl)benzaldehyde 
• 1033463-56-7 C₁₃H₁₄BrNO₃ 

Relevant articles and documents

Di[(R)-2-ethylhexyl] phthalate, a bioactive metabolite first isolated from three different bacillus species, and its synthesis

Di(2-ethylhexyl) phthalate (DEHP) is the most common phthalate ester, which has been used as a plasticizer for the production of numerous polymers, particularly polyvinyl chloride (PVC). Many other groups have synthesized meso-DEHP indicating interest in this molecule, but we are the first to synthesize enantiomerically pure di[(R)-2-ethylhexyl] phthalate. We report herein, for the first time, the isolation-from the cultures of Bacillus thuringiensis, B. subtilis, and B. velezensis strains-of di[(R)-2-ethylhexyl] phthalate, enantiomerically pure and in good yields: its biological activity against bacteria and fungi was probed and for the first time its synthesis was done.

Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.

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

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)-

Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones

Studies on the alkylation of enolates derived from a range of N-acyl-5,5-dimethyloxazolidin-2-ones and N-acyl-5,5-diphenyloxazolidin-2-ones reveal that high yields and high diastereoselectivities are best obtained when homochiral 4-isopropyl-5,5-dimethyloxazolidin-2-one is employed as a chiral auxiliary.

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.

Chiral auxiliaries

This invention relates to novel compounds of general formula (I): STR1 wherein the two R1 groups are identical lower alkyl groups or together form a lower alkylene group; R2 and R3 are both different and are selected from hydrogen atoms or organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R2 and R3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form. The compounds are useful chiral auxiliaries to which a wide range of, for example, acyl groups containing prochiral centers may be readily and reversibly coupled to the 3-position amino group.