Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate

Base Information

• Chemical Name: Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate
• CAS No.: 138616-36-1
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• DSSTox Substance ID: DTXSID20576595
• Nikkaji Number: J1.929.968F
• Wikidata: Q82466384
• Mol file: 138616-36-1.mol

Synonyms:138616-36-1;Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate;DTXSID20576595

Chemical Property of Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 240.115029749
• Heavy Atom Count: 18
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(CCC1)C#CC2=CC=CC=C2

Technology Process of Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate

There total 3 articles about Ethyl 2-(phenylethynyl)cyclopent-1-ene-1-carboxylate 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%

2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6) + phenylacetylene (536-74-3) → ethyl 2-(phenylethynyl)cyclopent-1-enecarboxylate (138616-36-1)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 55 ℃;

DOI:10.1021/jo034308v

Reference yield: 89.0%

tributylstannylethynylbenzene (3757-88-8) + 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6) → ethyl 2-(phenylethynyl)cyclopent-1-enecarboxylate (138616-36-1)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 55 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)93572-X

Reference yield:

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 2-(phenylethynyl)cyclopent-1-enecarboxylate (138616-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH

2: 89 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 55 °C

With sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)93572-X

upstream raw materials:

tributylstannylethynylbenzene

2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester

phenylacetylene

2-ethoxycarbonyl-1-cyclopentanone

Downstream raw materials:

2-(phenylethynyl)-cyclopent-1-ene-1-carboxylic acid

N-phenyl-2-(phenylethynyl)cyclopent-1-ene-1-carboxamide

6-phenyl-5-indanol

2-diazo-1-<2-(phenylethynyl)cyclopentenyl>-1-ethanone