Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)-

Base Information

• Chemical Name: Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)-
• CAS No.: 93452-03-0
• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.316
• European Community (EC) Number: 810-495-2
• UNII: 09QT06BTKM,9MCB9AC6FY
• DSSTox Substance ID: DTXSID80164856
• Nikkaji Number: J1.632.397G
• Wikidata: Q27236499
• Mol file: 93452-03-0.mol

Synonyms:Methyl epi-dihydrojasmonate;(-)-cis-Methyl dihydrojasmonate;UNII-09QT06BTKM;Methyl dihydrojasmonate, (-)-cis-;09QT06BTKM;FEMA No. 3408, (-)-cis-;151716-35-7;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S,2R)-;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)-;methyl dihydroepijasmonate;9MCB9AC6FY;methyl dihydrojasmonate (cis);SCHEMBL7941061;cis-(-)-methyl dihydrojasmonate;DTXSID80164856;Methyl dihydrojasmonate, cis-(+/-)-;METHYL DIHYDROJASMONATE, CIS-(-)-;methyl (+)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate;methyl (+/-)cis-3-oxo-2-pentyl-1-cyclopentaneacetate;Q27236499;methyl (+/-)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate;methyl (-)-(1S)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate;2beta-Pentyl-3-oxocyclopentane-1beta-acetic acid methyl ester;CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, CIS-;CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, (1R,2S)-REL-;CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, CIS-(+/-)-;93452-03-0

Chemical Property of Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)-

Chemical Property:

• Boiling Point: 292-293℃ at 97.1-101.3kPa
• Density: 1.007 at 20℃
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 226.15689456
• Heavy Atom Count: 16
• Complexity: 248

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1C(CCC1=O)CC(=O)OC
• Isomeric SMILES: CCCCC[C@@H]1[C@@H](CCC1=O)CC(=O)OC

Technology Process of Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)-

There total 44 articles about Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-cis)- 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%

(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 hydrogen; palladium on activated charcoal; In methanol; for 24h; under 760 Torr; Ambient temperature;

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

Reference yield: 93.0%

((1R,2S,3R)-3-Hydroxy-2-pentyl-cyclopentyl)-acetic acid methyl ester (54562-27-5,84893-69-6,108102-95-0,109008-64-2,109361-58-2,109361-60-6,119009-18-6,119009-19-7,136845-16-4,143292-36-8,146143-16-0) → (+/-)-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 dipyridinium dichromate; In dichloromethane; for 44h;

Reference yield:

2-pentyl-2-cyclopenten-1-one (25564-22-1) → (+/-)-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:

Multi-step reaction with 4 steps

1.1: LiCl; CuI / diethyl ether; tetrahydrofuran / 0.08 h / -80 °C

1.2: diethyl ether; tetrahydrofuran / 1 h / -80 - -30 °C

1.3: 70 percent / 2-(methyliminomethyl)phenol / diethyl ether; tetrahydrofuran / -80 - 20 °C

2.1: O₃ / CH₂Cl₂ / 0.25 h / -80 °C

2.2: 70 percent / Me₂S / CH₂Cl₂ / -80 - 20 °C

3.1: NaH₂PO₄*H₂O; 30percent H₂O₂; NaClO₂ / H₂O; acetonitrile / 24 h / 20 °C

4.1: diethyl ether; methanol / 0.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; ozone; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1002/1099-0690(200110)2001:20<3837::AID-EJOC3837>3.0.CO;2-3

upstream raw materials:

(3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester

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

((1R,2S,3R)-3-Hydroxy-2-pentyl-cyclopentyl)-acetic acid methyl ester

3-methoxycarbonylmethyl-2-(1-phenylthiopentyl)cyclopentanone

Downstream raw materials:

(+)-9,10-dihydro-7-iso-jasmonic acid

(+/-)-methyl trans-dihydrojasmonate