N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8A,9S)-6'-methoxy-9-cinchonanyl]thiourea

Base Information

• Chemical Name: N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8A,9S)-6'-methoxy-9-cinchonanyl]thiourea
• CAS No.: 852913-16-7
• Molecular Formula: C29H28F6N4OS
• Molecular Weight: 594.624
• Hs Code.: 29339900
• European Community (EC) Number: 635-380-2
• ChEMBL ID: CHEMBL3746148
• DSSTox Substance ID: DTXSID20469776
• Nikkaji Number: J2.950.383D,J2.178.290D
• Mol file: 852913-16-7.mol

Synonyms:852913-16-7;N-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-N'-[(8A,9S)-6'-METHOXY-9-CINCHONANYL]THIOUREA;1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea;9-(3-(3,5-Bis(trifluoromethyl)phenyl)thioureido)-(epi-quinine);1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8|A,9S)-6'-methoxycinchonan-9-yl]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;MFCD16875670;AMY883;CHEMBL3746148;SCHEMBL15544103;DTXSID20469776;IQMKPBFOEWWDIQ-FRSFCCSCSA-N;CJB91316;AKOS030527512;AS-53275;CS-0028351;P16273;A904227;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8,9S)-6'-methoxycinchonan-9-yl]thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8a,9S)-6'-methoxy-9-cinchonanyl]thiourea, 90%;N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8alpha,9S)-6'-methoxy-9-cinchonanyl]thiourea;N-[3,5-Bis(trifluoromethyl)phenyl]-N(2)-[(8a,9S)-6(2)-methoxy-9-cinchonanyl]thiourea

Chemical Property of N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8A,9S)-6'-methoxy-9-cinchonanyl]thiourea

Chemical Property:

• Boiling Point: 598.2±60.0 °C(Predicted)
• PKA: 11.39±0.70(Predicted)
• PSA: 88.55000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 7.75440
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 594.18880168
• Heavy Atom Count: 41
• Complexity: 912

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-6′-methoxy-9-cinchonanyl]thiourea 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)NC(=S)NC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F
• Isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)NC(=S)NC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F
• Uses: N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-6′-methoxy-9-cinchonanyl]thiourea is a bifunctional cinchona organocatalyst, which can be used to synthesize: Stereoselective diaryl(nitro)butanone via enantioselective Michael addition of nitromethane to chalcones. Enantioselective β-amino acids via asymmetric Mannich reaction of malonates with aryl and alkyl imines. The synthesis of 3-indolylmethanamines by the reaction of indoles with imines via asymmetric Friedel-Crafts reaction. The enantioselective conjugate addition of active methylene compounds to enones to obtain the corresponding addition products.

Technology Process of N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8A,9S)-6'-methoxy-9-cinchonanyl]thiourea

There total 8 articles about N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8A,9S)-6'-methoxy-9-cinchonanyl]thiourea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) + 9-amino-9-deoxy-epiquinine → 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea (852913-16-7)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.1c02211

Reference yield: 91.0%

3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) + (8α, 9S)-9-amine-6'-methoxycinchonan (189309-10-2) → 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea (852913-16-7)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01962

Reference yield: 32.0%

(S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanamine (1381884-75-8,168960-95-0) + 3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) → C29H28F6N4OS (852913-16-7)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

DOI:10.3998/ark.5550190.0012.930

upstream raw materials:

3,5-bistrifluoromethylphenylisothiocyanate

(8S,9S)-9-azido-(9-deoxy)epiquinine

Quinine

thiourea

Refernces

• 1、 Sakai, Naoki,Kawashima, Kyohei,Kajitani, Masashi,Mori, Seiji,Oriyama, Takeshi. "Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid". supporting information. p. 5714 - 5718. Retrieved 2021/08/01.
• 2、 Asano, Keisuke,Matsubara, Seijiro. "Asymmetric Cycloetherification by Bifunctional Organocatalyst". supporting information. p. 4243 - 4253. Retrieved 2018/07/03.