852913-16-7

Basic information

• Product Name: Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl) phenylthiourea
• Synonyms: Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl) phenylthiourea;N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(8α,9S)-6'-Methoxycinchonan-9-yl]- Thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8a,9S)-6'-methoxy-9-cinchonanyl]thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8a,9S)-6'-methoxy-9-cinchonanyl]thiourea 90%; 1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-3-[(S)(6-METHOXY-4-QUINOLINYL)-[(2S,4S,5R)-5-VINYL-1-AZA-BICYCLO[2.2.2]OCT-2-YL]METHYL]THIOUREA;1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl]thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8α,9S)-6'-methox ycinchonan-9-yl]thiourea,99%d.e.;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea
• CAS NO: 852913-16-7
• Molecular Formula: C₂₉H₂₈F₆N₄OS
• Molecular Weight: 594.6142392
• Mol File: 852913-16-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 598.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 11.39±0.70(Predicted)
• CAS DataBase Reference: Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl) phenylthiourea(CAS DataBase Reference)
• NIST Chemistry Reference: Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl) phenylthiourea(852913-16-7)
• EPA Substance Registry System: Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl) phenylthiourea(852913-16-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 852913-16-7(Hazardous Substances Data)

Usage

Description

Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea is a bifunctional cinchona organocatalyst, characterized by its solid chemical properties. It is known for its ability to facilitate various chemical reactions with high stereoselectivity, making it a valuable compound in the field of organic synthesis.

Uses

Used in Pharmaceutical Industry:
Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea is used as a chiral organocatalyst for the enantioselective synthesis of pharmaceutical compounds. Its ability to induce high stereoselectivity in chemical reactions allows for the production of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs.
Used in Chemical Synthesis:
Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea is used as a catalyst in the synthesis of various organic compounds, including:
1. Stereoselective diaryl(nitro)butanone via enantioselective Michael addition of nitromethane to chalcones.
2. Enantioselective β-amino acids via asymmetric Mannich reaction of malonates with aryl and alkyl imines.
3. The synthesis of 3-indolylmethanamines by the reaction of indoles with imines via asymmetric Friedel-Crafts reaction.
4. The enantioselective conjugate addition of active methylene compounds to enones to obtain the corresponding addition products.
These applications highlight the versatility of Epi-N-Quinyl-N’-bis(3,5-trifluoromethyl)phenylthiourea as a catalyst in various organic reactions, contributing to the advancement of chemical synthesis and the development of new compounds with potential applications in various industries.

Upstream product

• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 168778-61-8 (8S,9S)-9-azido-(9-deoxy)epiquinine 
• 130-95-0 Quinine 
• 17356-08-0 thiourea 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 189309-10-2 (8α, 9S)-9-amine-6'-methoxycinchonan 
• 249731-47-3 9-mesylquinine 
• 130-95-0 quinine 
• 1381884-75-8 (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanamine 

Relevant articles and documents

Access to Chiral Polycyclic 1,4-Dihydropyridines via Organocatalytic Formal [3 + 3] Annulation of 2-(1-Alkynyl)-2-alken-1-ones with 3-Aminobenzofurans

A rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst is described, affording biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields (43-82%) with good to excellent enantioselectivities (83-99%). This formal [3 + 3] annulation reaction reveals good practicality when conducted on a gram scale, and the cycloadduct has the capability for further elaborations.

Highly enantioselective aza-henry reaction of ketimines catalyzed by a chiral bifunctional thiourea-tertiary amine derived from quinine

We have developed a highly enantioselective aza-Henry reaction of aryl α-ketoester-derived N-Ts ketimines with a wide range of substrate scope by a simpler bifunctional thiourea-tertiary amine catalyst derived from quinine. A variety of ketimines were investigated and corresponding products were obtained in excellent yields (up to 99% yield) with excellent enatioselectivities (up to 99% ee).

Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids

The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.