157904-67-1

Basic information

• Product Name: (4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyl-Oxazole
• Synonyms: (4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyl-Oxazole;(4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene 95%;(4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyloxazole],99%e.e.;(4R,4μR,5S,5μS)-2,2μ-(1-Methylethylidene;2,2-Bis[2-(4R,5S-diphenyl-1,3-oxazolinyl)]propane, 95%
• CAS NO: 157904-67-1
• Molecular Formula: C33H30N2O2
• Molecular Weight: 486.6035
• Mol File: 157904-67-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 164-169°C
• Boiling Point: 606.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.33±0.70(Predicted)
• CAS DataBase Reference: (4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyl-Oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyl-Oxazole(157904-67-1)
• EPA Substance Registry System: (4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyl-Oxazole(157904-67-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 157904-67-1(Hazardous Substances Data)

Usage

Uses

(4R,4′R,5S,5′S)-2,2′-(1-Methylethylidene) or (4S,5R)-Bis-Phbox) can be used as a ligand:To prepare selective exo-catalysts for enantioselective 1,3-dipolar cycloaddition reactions. In the asymmetric aminooxygenation of alkenes in the presence of tetramethylaminopyridyl radical (TEMPO) as an oxidant and copper(II) triflate as a catalyst.In asymmetric aminofluorination of olefins using an iron catalyst.This chiral Box ligand was most recently shown to mediate an asymmetric aminofluorination of olefins utlizing Xtalfuor-E (719439) and TREAT-HF (344648). The resulting cyclic carbamates can be readily converted into their concomitant beta-fluoro amino acids.

Upstream product

• 595-46-0 2,2-dimethylmalonic acid 
• 5659-93-8 2,2-Dimethylmalonyl chloride 
• 183866-68-4 N,N'-Bis-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2,2-dimethyl-malonamide 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 

Relevant articles and documents

SYNTHESIS OF SMALL MOLECULES INSPIRED BY PHOMOXANTHONE A

Methods, compositions, and kits are provided for synthesizing bioactive chromane, the method including: constructing a tertiary ether stereocenter enantioselectively by catalyzed alkynylation of a substituted chromenone to obtain a chromanone; reducing alkyne and ketone in the chromanone to obtain a chroman; and converting ester to methyl group thereby obtaining chromane.

Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes

The enantioselective hydroarylation of vinylarenes catalyzed by a chiral, non-racemic nickel catalyst is presented as a facile method to generate chiral 1,1-diarylethanes. These reactions proceed via formation of a chiral, non-racemic nickel benzyl intermediate. Transmetalation with arylboron nucleophiles and subsequent reductive elimination enable the formation of a variety of chiral 1,1-diarylethanes. The 1,1-diarylethane products from reactions of arylboronic acids containing electron-donating substituents are formed with typically greater than 90% ee, while the 1,1-diarylethanes generated from reactions of arylboronic acids containing electron-withdrawing groups are generated with typically less than 80% ee. These results are consistent with the rate of transmetalation with an arylboron nucleophile playing a key role in the enantioselectivity of these hydroarylation reactions. This mechanistic insight has led to the development of reactions of neo-pentylglycolate esters of arylboronic acids with vinylarenes that occur with higher enantioselectivities based on increased rates of transmetalation.