620960-26-1

Basic information

• Product Name: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)
• Synonyms: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC);1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea (R,R-TUC);1-[3,5-Bis(trifluoroMethyl)phenyl]-3-[(1R,2R) -2-(diMethylaMino)cyclohexyl]thiourea;Thiourea, N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(1R,2R)-2-(diMethylaMino)cyclohexyl]-;1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2- (dimethylamino)cyclohexyl]thiourea,99%e.e.
• CAS NO: 620960-26-1
• Molecular Formula: C17H21F6N3S
• Molecular Weight: 413.428
• Product Categories: organic amine
• Mol File: 620960-26-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 87-88°C
• Boiling Point: 380.8±52.0 °C(Predicted)
• Appearance: white/Powder
• Density: 1.33±0.1 g/cm3(Predicted)
• PKA: 11.76±0.70(Predicted)
• CAS DataBase Reference: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)(620960-26-1)
• EPA Substance Registry System: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)(620960-26-1)

Safety Data

• Hazardous Substances Data: 620960-26-1(Hazardous Substances Data)

Usage

Reaction

Thiourea catalyst used in the enantio and diastereoselective Michael addition of malonates and ketoesters to nitroolefins. Catalyst used in the enantioselective hydrazination of 1,3-dicarbonyl compounds. Catalyst used for the dynamic resolution of azalactones. Catalyst used in Michael-Aldol reaction of 2-mercaptobenzaldehyde with α,β-unsaturated oxazolidinone. Catalyst for enantioselective synthesis of flavanones and chromanones. Catalyst for the asymmetric Neber Reaction. Catalyst for the three component synthesis of 2,6-diazabicyclo[2.2.2]octanones.

Upstream product

• 320778-92-5 (1R,2R)-N,N-dimethylcyclohexane-1,2-diamine 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 75-15-0 carbon disulfide 
• 67198-21-4 (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 860994-58-7 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea 
• 50-00-0 formaldehyd 
• 894493-95-9 (1S,2S)-N,N-dimethylcyclohexane-1,2-diamine 
• 67-66-3 chloroform 

Relevant articles and documents

Enantioselective construction of quaternary carbon centre catalysed by bifunctional organocatalyst

A highly efficient organocatalytic method for the asymmetric Michael addition of α-substituted cyanoacetates to vinyl sulfones was investigated. It was observed that this reaction was synergistically promoted by readily available bifunctional thiourea-ter

A simplified synthesis of Takemoto's catalyst

A facile two-step procedure for the preparation of Takemoto's catalyst is reported. The thiourea moiety was obtained by condensation of 3,5-bis(trifluoromethyl)aniline with phenyl chlorothioformate and in situ substitution of phenol by trans-1,2-diaminocy

Directing the Activation of Donor–Acceptor Cyclopropanes Towards Stereoselective 1,3-Dipolar Cycloaddition Reactions by Br?nsted Base Catalysis

The first stereoselective organocatalyzed [3+2] cycloaddition reaction of donor-acceptor cyclopropanes is presented. It is demonstrated that by applying an optically active bifunctional Br?nsted base catalyst, racemic di-cyano cyclopropylketones can be activated to undergo a stereoselective 1,3-dipolar reaction with mono- and polysubstituted nitroolefins. The reaction affords functionalized cyclopentanes with three consecutive stereocenters in high yield and stereoselectivity. Based on the stereochemical outcome, a mechanism in which the organocatalyst activates both the donor-acceptor cyclopropane and nitroolefin is proposed. Finally, chemoselective transformations of the cycloaddition products are demonstrated.

Asymmetric isomerization of ω-hydroxy-α,β-unsaturated thioesters into β-mercaptolactones by a bifunctional aminothiourea catalyst

We present a novel methodology for the asymmetric synthesis of β-mercaptolactones via isomerization of ω-hydroxy-α,β- unsaturated thioesters by means of a bifunctional aminothiourea catalyst. The catalyst interacts with the substrate through the cooperati