Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate

Base Information

• Chemical Name: Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate
• CAS No.: 122539-74-6
• Molecular Formula: C9H11F3O5S
• Molecular Weight: 288.245
• Hs Code.: 2916209090
• European Community (EC) Number: 631-410-3
• DSSTox Substance ID: DTXSID80381586
• Nikkaji Number: J306.026H
• Wikidata: Q72477571
• Mol file: 122539-74-6.mol

Synonyms:122539-74-6;Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate;Ethyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate;Ethyl 2-{[(trifluoromethyl)sulphonyl]oxy}cyclopent-1-ene-1-carboxylate;Ethyl 2-(trifluoromethylsulfonyloxy)cyclopentene-1-carboxylate;ETHYL 2-([(TRIFLUOROMETHYL)SULPHONYL]OXY)CYCLOPENT-1-ENE-1-CARBOXYLATE;Ethyl 2-(((trifluoromethyl)sulfonyl)-oxy)cyclopent-1-enecarboxylate;ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate;SCHEMBL1957632;DTXSID80381586;ethyl 2-(trifluoromethanesulfonyloxy)cyclopent-1-ene-1-carboxylate;MFCD00209586;AKOS015852970;ETHYL 2-(TRIFLUOROMETHYLSULFONYLOXY)-1-CYCLOPENTENE-1-CARBOXYLATE;PS-10673;CS-0206813;A891100;J-004819;ethyl 2-trifluoromethanesulfonyloxycyclopent-1-enecarboxylate;Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclopent-1-ene-1-carboxylate;Ethyl2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate;2-[(Trifluoromethylsulfonyl)oxy]cyclopentene-1-carboxylic acid ethyl ester;2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester;ethyl 2-{[(trifluormethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate;ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate

Chemical Property of Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate

Chemical Property:

• Melting Point: 74 °C/0.5 mmHg(lit.)
• Refractive Index: n20/D 1.428(lit.)
• Boiling Point: 74ºC/0.5 mmHg(lit.)
• Flash Point: 113 °C
• PSA: 78.05000
• Density: 1.35 g/mL at 25 °C(lit.)
• LogP: 2.93450
• Storage Temp.: Refrigerated.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 288.02792911
• Heavy Atom Count: 18
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(CCC1)OS(=O)(=O)C(F)(F)F

Technology Process of Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate

There total 7 articles about Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate 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: 99.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6)

Guidance literature:

With sodium hydride; In diethyl ether;

DOI:10.1002/hlca.200900003

Reference yield: 97.0%

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6)

Guidance literature:

With trifluoromethanesulfonic acid anhydride; triethylamine; In dichloromethane;

Reference yield: 84.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6)

Guidance literature:

2-ethoxycarbonyl-1-cyclopentanone; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; for 0.5h;

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

2-ethoxycarbonyl-1-cyclopentanone

trifluoromethylsulfonic anhydride

trifluoromethanesulfonic acid anhydride

Downstream raw materials:

ethyl 2-(phenylethynyl)cyclopent-1-enecarboxylate

ethyl 2-(4-formylphenylethynyl)cyclopentenecarboxylate

ethyl 2-(2-(2-phenylphenyl)ethynyl)cyclopent-1-enecarboxylate

ethyl 2-(4-phenyl-1-butynyl)-1-cyclopentenecarboxylate

Refernces

• 1、 Minnaard, Adriaan J.,Santiago, Isabel Nu?ez,Uiterweerd, Michiel T.,van Wezel, Gilles P.,van der Heul, Helga. "Iso-maleimycin, a Constitutional Isomer of Maleimycin, from Streptomyces sp. QL37". . . Retrieved 2020.
• 2、 Kizhakkayil Mangadan, Arun Raj,Liu, Ji,Aponick, Aaron. "Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry". supporting information. p. 22224 - 22229. Retrieved 2021/09/09.