959979-30-7

Basic information

• Product Name: (2S)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]thioxomethyl]amino]-N-3,3-trimethyl-N-(phenylmethyl)butanamide
• Synonyms: (2S)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]thioxomethyl]amino]-N-3,3-trimethyl-N-(phenylmethyl)butanamide;(S)-2-[[3,5-Bis(trifluoromethyl)phenyl]thioureido]-N-benzyl-N,3,3-trimethylbutanamide;(R)-Ru(OAc)2(SEGPHOS(R));ButanaMide, 2-[[[[3,5-bis(trifluoroMethyl)phenyl]aMino]thioxoMethyl]aMino]-N,3,3-triMethyl-N-(phenylMethyl)-, (2S)-;(S)-2-[[3,5-Bis(trifluoromethyl)phenyl]thioureido]-N-benzyl-N,3,3-trimethylbutanamide 97%;(S)-2-[[3,5-Bis(trifluoromethyl)phenyl]thioureido]-Nbenzyl- N,3,3-trimethylbutanamide,99%e.e.;(2S)-N-benzyl-2-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]-N,3,3-trimethylbutanamide
• CAS NO: 959979-30-7
• Molecular Formula: C₂₃H₂₅F₆N₃OS
• Molecular Weight: 505.5195192
• Mol File: 959979-30-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 147-152 °C
• Boiling Point: 497.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.305±0.06 g/cm3(Predicted)
• PKA: 11.41±0.70(Predicted)
• CAS DataBase Reference: (2S)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]thioxomethyl]amino]-N-3,3-trimethyl-N-(phenylmethyl)butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]thioxomethyl]amino]-N-3,3-trimethyl-N-(phenylmethyl)butanamide(959979-30-7)
• EPA Substance Registry System: (2S)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]thioxomethyl]amino]-N-3,3-trimethyl-N-(phenylmethyl)butanamide(959979-30-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 959979-30-7(Hazardous Substances Data)

Usage

Uses

Versatile catalyst for reactions including the Mannich reaction.

General Description

(S)-2-[[3,5-Bis(trifluoromethyl)phenyl]thioureido]-N-benzyl-N,3,3-trimethylbutanamide is a chiral thiourea organocatalyst developed by the Jacobsen′s group for asymmetric organic synthesis.

Upstream product

• 1032509-62-8 tert-butyl (S)-1-(N-benzyl-N-methylcarbamoyl)-2,2-dimethylpropylcarbamate 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 947383-62-2 (S)-t-leucine N-benzyl-N-methyl-amide 
• 103-67-3 benzyl-methyl-amine 
• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 

Relevant articles and documents

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Enantioselective thiourea-catalyzed additions to oxocarbenium ions

Asymmetric, catalytic reactions of oxocarbenium ions are reported. Simple, chiral urea and thiourea derivatives are shown to catalyze the enantioselective substitution of silyl ketene acetals onto 1-chloroisochromans. A mechanism involving anion binding by the chiral catalyst to generate a reactive oxocarbenium ion is invoked. Catalysts bearing tertiary benzylic amide groups afforded highest enantioselectivities, with the optimal structure being derived from enantioenriched 2-arylpyrrolidine derivatives. Copyright