1-Cyclohexene-1-carboxylic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester

Base Information

• Chemical Name: 1-Cyclohexene-1-carboxylic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester
• CAS No.: 93493-95-9
• Molecular Formula: C9H11F3O5S
• Molecular Weight: 288.245
• Mol file: 93493-95-9.mol

Synonyms:methyl 2-(trifluoromethylsulfonyloxy)cyclohex-1-enecarboxylate;2-methylcarboxyl-1-cyclohexenyl triflate;2-Trifluoromethanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester;methyl 2-(trifluoromethanesulfonyloxy)-1-cyclohexenecarboxylate;methyl 2-trifluoromethanesulfonyloxy-1-cyclohexene-1-carboxylate;

Chemical Property of 1-Cyclohexene-1-carboxylic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester

Chemical Property:

• Boiling Point: 311.3±42.0 °C(Predicted)
• PSA: 78.05000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 2.93450

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Cyclohexene-1-carboxylic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester

There total 4 articles about 1-Cyclohexene-1-carboxylic acid, 2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester 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: 100.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-(methoxycarbonyl)cyclohexanone (41302-34-5) → 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-enecarboxylic acid methyl ester (93493-95-9)

Guidance literature:

2-(methoxycarbonyl)cyclohexanone; With sodium hydride; In dichloromethane; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

trifluoromethylsulfonic anhydride; In dichloromethane; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01694

Reference yield: 90.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2-(methoxycarbonyl)cyclohexanone (41302-34-5) → 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-enecarboxylic acid methyl ester (93493-95-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1016/j.bmcl.2011.03.094

Reference yield: 79.0%

2-(methoxycarbonyl)cyclohexanone (41302-34-5) + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-enecarboxylic acid methyl ester (93493-95-9)

Guidance literature:

2-(methoxycarbonyl)cyclohexanone; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1021/jm100022r

upstream raw materials:

trifluoromethylsulfonic anhydride

2-(methoxycarbonyl)cyclohexanone

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

N,N-phenylbistrifluoromethane-sulfonimide

Downstream raw materials:

2-(4-aminomethyl-phenyl)-cyclohex-1-enecarboxylic acid methyl ester

Refernces

• 1、 -. "Novel BCL-2/BCL-XL inhibitor, pharmaceutical composition and application". Paragraph 0045-0048; 0050; 0052-0053. . Retrieved 2020/11/12.
• 2、 Peil, Sebastian,Fürstner, Alois. "Mechanistic Divergence in the Hydrogenative Synthesis of Furans and Butenolides: Ruthenium Carbenes Formed by gem-Hydrogenation or through Carbophilic Activation of Alkynes". supporting information. p. 18476 - 18481. Retrieved 2019/11/14.