1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)

Base Information

• Chemical Name: 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)
• CAS No.: 620960-26-1
• Molecular Formula: C₁₇H₂₁F₆N₃S
• Molecular Weight: 413.43
• Mol file: 620960-26-1.mol

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]-

Chemical Property of 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)

Chemical Property:

• Melting Point: 87-88°C
• Boiling Point: 380.8±52.0 °C(Predicted)
• PKA: 11.76±0.70(Predicted)
• PSA: 59.39000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 5.34730

Purity/Quality:

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

^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC)

There total 8 articles about 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-(-)-2-(dimethylamino)cyclohexyl]thiourea(R,R-TUC) 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: 93.0%

1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea (860994-58-7) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea (620960-26-1)

Guidance literature:

1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; formaldehyd; In 1,2-dichloro-ethane; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 6h; Inert atmosphere;

With sodium hydrogencarbonate; In water; 1,2-dichloro-ethane; for 0.25h;

DOI:10.1002/adsc.201200558

Reference yield: 84.0%

(1R,2R)-N,N-dimethylcyclohexane-1,2-diamine (320778-92-5) + 3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) → 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea (620960-26-1)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1039/b607574f

Reference yield: 75.0%

(1S,2S)-N,N-dimethylcyclohexane-1,2-diamine (894493-95-9) + 3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) → 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea (620960-26-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b605871j

upstream raw materials:

(1R,2R)-N,N-dimethylcyclohexane-1,2-diamine

3,5-bistrifluoromethylphenylisothiocyanate

carbon disulfide

(±)-N,N-dimethyl-trans-1,2-diaminocyclohexane

Refernces

• 1、 Jiang, Lin,Zheng, Hong-Ting,Liu, Tian-Yu,Yue, Lei,Chen, Ying-Chun. "Asymmetric direct vinylogous carbon-carbon bond formation catalyzed by bifunctional organocatalysts". . p. 5123 - 5128. Retrieved 2007.
• 2、 Blom, Jakob,Vidal-Albalat, Andreu,J?rgensen, Julie,Barl?se, Casper L.,Jessen, Kamilla S.,Iversen, Marc V.,J?rgensen, Karl Anker. "Directing the Activation of Donor–Acceptor Cyclopropanes Towards Stereoselective 1,3-Dipolar Cycloaddition Reactions by Br?nsted Base Catalysis". . p. 11831 - 11835. Retrieved 2017/09/20.
• 3、 Massolo, Elisabetta,Benaglia, Maurizio,Genoni, Andrea,Annunziata, Rita,Celentano, Giuseppe,Gaggero, Nicoletta. "Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent". supporting information. p. 5591 - 5596. Retrieved 2015/05/27.