852913-25-8

Basic information

• Product Name: N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]- Thiourea
• Synonyms: N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]- Thiourea;N-[3,5-Bis(trifluoroMethyl)phenyl]-N′-[(9R)-6′-Methoxy-9-cinchonanyl]thiourea;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxy-9-cinchonanyl]thiourea >=90.0%;1-(3,5-Bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinucli;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxyci nchonan-9-yl]thiourea,99%d.e.;1-[3,5-bis(trifluoromethyl)phenyl]-3-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea
• CAS NO: 852913-25-8
• Molecular Formula: C₂₉H₂₈F₆N₄OS
• Molecular Weight: 594.6142392
• Mol File: 852913-25-8.mol

Chemical Properties

• Melting Point: 150 °C (decomp)
• Boiling Point: 598.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.39±0.70(Predicted)
• CAS DataBase Reference: N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]- Thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]- Thiourea(852913-25-8)
• EPA Substance Registry System: N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]- Thiourea(852913-25-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 852913-25-8(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]Thiourea is used as a catalyst for enantioselective Mannich reactions, which are crucial in the synthesis of optically active compounds. This application is particularly important in the pharmaceutical industry, where the production of enantiomerically pure compounds is essential for the development of effective and safe drugs.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]Thiourea is used as a catalyst for the formation of optically active Mannich adducts from stable N-carbamate amido sulfones. This process is vital for the synthesis of chiral compounds, which are often the active ingredients in medications. The use of this catalyst allows for the production of these compounds with high enantioselectivity, ensuring the desired biological activity and minimizing potential side effects.
Used in Chemical Research:
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(9R)-6'-Methoxycinchonan-9-yl]Thiourea is also used in chemical research as a versatile catalyst for various asymmetric reactions. Its unique structure and properties make it a valuable tool for chemists working on the development of new synthetic methods and the synthesis of complex organic molecules with specific stereochemistry. This can be particularly useful in the discovery and optimization of new pharmaceutical agents, agrochemicals, and other specialty chemicals.

Upstream product

• 866140-03-6 (8R,9R)-9-azido-(9-deoxy)epiquinidine 
• 56-54-2 quinidine 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 287979-82-2 9-amino-9-deoxyepiquinidine 

Relevant articles and documents

Organocatalytic Enantio- and Diastereoselective Construction of syn-1,3-Diol Motifs via Dynamic Kinetic Resolution of in Situ Generated Chiral Cyanohydrins

An organocatalytic method for the asymmetric synthesis of syn-1,3-dioxanes as protected 1,3-diols via dynamic kinetic resolution of in situ generated chiral cyanohydrins has been developed. This method involves a reversible cyanohydrin formation/hemiaceta

TRANSFORMATIONS OF MESO-LACTIDE

B/N Lewis pairs have been discovered to catalyze rapid epimerization of meso-lactide (LA) or LA diastereomers quantitatively into rac-LA. The obtained rac-LA can be kinetically polymerized into poly(L-lactide) and optically resolved D-LA, with a high stereoselectivity factor kL/kD of 53 and an ee value of 91% at 50.6% monomer conversion, by a bifunctional chiral catalyst. The epimerization and enantioselective polymerization can be coupled into a one-pot process for transforming meso-LA directly into poly(L-lactide) and D-LA.

Asymmetric Cycloetherification by Bifunctional Organocatalyst

Attempts to obtain enantiomerically enriched tetrahydrofuran derivatives via an intramolecular oxy -Michael addition reaction of ?-hydroxyenone is discussed. Despite previous difficulties associated with the asymmetric induction of this reaction, which can proceed even without a catalyst, a highly efficient asymmetric induction was realized using a bifunctional organocatalyst derived from a cinchona alkaloid. The reaction could be extended to ζ-hydroxyenone to yield an optically active tetrahydropyran derivative with a high ee. In these reactions, it is important for the gentle acidic and basic sites in the bifunctional organocatalyst to be arranged properly within the molecular skeleton of the catalyst. The high performance asymmetric induction relied on the affinity of the catalyst for the substrate, which played an important role. A disubstituted tetrahydropyran synthesis could be effectively performed via kinetic resolution using ζ-hydroxyenone containing a secondary alcohol moiety using a chiral phosphoric acid catalyst.

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

Procedure-controlled enantioselectivity switch in organocatalytic 2-oxazolidinone synthesis

In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.

Asymmetric catalytic cycloetherification mediated by bifunctional organocatalysts

Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalytic cycloetherification of ε-hydroxy-α,β- unsaturated ketones mediated by cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.