1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

Base Information

• Chemical Name: 1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester
• CAS No.: 24863-70-5
• Molecular Formula: C13H20O3
• Molecular Weight: 224.3
• European Community (EC) Number: 431-410-1,607-449-7
• DSSTox Substance ID: DTXSID10179574
• Nikkaji Number: J144.669J
• Wikidata: Q83050108
• Mol file: 24863-70-5.mol

Synonyms:24863-70-5;1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester;methyl 2-(3-oxo-2-pentylcyclopent-1-en-1-yl)acetate;EC 607-449-7;methyl 2-(3-oxo-2-pentylcyclopenten-1-yl)acetate;SCHEMBL2142693;DTXSID10179574;methyl 3-oxo-2-pentyl-1-cyclopentene-acetate;methyl-3-oxo-2-pentyl-1-cyclopentene-acetate;EC 431-410-1;methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate;methyl(2-pentyl-3-keto-1-cyclopentenyl-)acetate;methyl (2-pentyl-3-keto-1-cyclopentenyl-)acetate;methyl (3-oxo-2-pentylcyclopent-1-en-1-yl)acetate;methyl2-(3-oxo-2-pentylcyclopent-1-en-1-yl)acetate;2-Pentyl-3-oxo-1-cyclopentene-1-acetic acid methyl ester

Chemical Property of 1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

Chemical Property:

• Vapor Pressure: 0.000202mmHg at 25°C
• Refractive Index: 1.475
• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 141.6 °C
• PSA: 43.37000
• Density: 1.023 g/cm³
• LogP: 2.78930
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 224.14124450
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(CCC1=O)CC(=O)OC

Technology Process of 1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester

There total 3 articles about 1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, 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:

(+/-)-Methyl t-3-acetoxy-c-2,3-epoxy-2-pentyl-r-1-cyclopentaneacetate → dihydro-cis-jasmone (1128-08-1) + (3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester (24863-70-5) + (+/-)-cis-1-Pentyl-2-oxabicyclo[3.3.0]octane-3,8-dione

Guidance literature:

With methanesulfonic acid; In methanol; for 2h; Heating;

DOI:10.1055/s-2001-15149

Reference yield:

3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester (128893-61-8) → (3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester (24863-70-5) + (+/-)-methyl dihydroepijasmonate (2570-03-8,2630-39-9,24851-98-7,39647-11-5,93452-03-0,133163-97-0,133163-98-1,128087-96-7)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) iPrOH, 65 deg C, electrolysis, 2.) MeOH, room temp., 24h;

DOI:10.1016/S0040-4039(00)88791-2

Reference yield:

methanol (67-56-1) + 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester (128893-61-8) → (3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester (24863-70-5) + (+/-)-methyl trans-dihydrojasmonate (2570-03-8,128087-96-7)

Guidance literature:

With hydrogenchloride; tetraethylammonium tosylate; Yield given. Multistep reaction. Yields of byproduct given; 1) isopropanol, 65 deg C, electroreduction (Sn-cathode), 2) r. t., 12 h;

DOI:10.1021/jo00052a036

upstream raw materials:

methanol

3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester

Downstream raw materials:

methyl dihydro jasmonate

(-)-cis-Methyl dihydrojasmonate

trans-methyl ((1S,2S)-2-pentyl-3-oxocyclopentyl)acetate

cis methyl dehydrojasmonate

Refernces

• 1、 Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Tominaga, Naoto,Morita, Hiroshi. "Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles". . p. 7175 - 7187. Retrieved 2007/10/02.