Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate

Base Information

• Chemical Name: Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate
• CAS No.: 109959-42-4
• Deprecated CAS: 53369-26-9
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• DSSTox Substance ID: DTXSID201022118
• Mol file: 109959-42-4.mol

Synonyms:Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate;Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2S)-rel-;Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2S)-rel-;42536-97-0;(e)-methyl jasmonate;SCHEMBL14446250;GEWDNTWNSAZUDX-NNOMMRTBSA-N;DTXSID201022118;Methyl {(1S,2S)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl}acetate;109959-42-4

Chemical Property of Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 224.14124450
• Heavy Atom Count: 16
• Complexity: 281

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC=CCC1C(CCC1=O)CC(=O)OC
• Isomeric SMILES: CC/C=C/C[C@H]1[C@@H](CCC1=O)CC(=O)OC

Technology Process of Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate

There total 151 articles about Methyl (Z)-(cis)-3-oxo-2-(2-pentenyl)cyclopentaneacetate 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%

(2R*,3S*)-3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanone (29119-47-9,114029-37-7,37435-88-4,82423-75-4,83648-24-2,131063-53-1) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With hydrogen; Lindlar's catalyst; In toluene; at 20 ℃; for 3h;

DOI:10.1016/S0022-328X(01)00890-7

Reference yield: 95.0%

Methyl 6-oxo-2(E)-dodecen-9-ynoate (73205-94-4) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In methanol; for 1h; under 3677.5 Torr; Ambient temperature;

Reference yield: 90.0%

trans-2-(cis-2-pentenyl)-3-<(methoxycarbonyl)(trimethylsilyl)methyl>cyclopentane-1-one (72049-88-8) → methyl jasmonate (1211-29-6,20073-13-6,39924-52-2,42536-97-0,53369-26-9,62653-86-5,78609-06-0,93452-02-9,95722-42-2,109959-42-4,136233-36-8)

Guidance literature:

With potassium fluoride; In methanol; water; Ambient temperature;

DOI:10.1021/jo01290a006

upstream raw materials:

2-methoxycarbonyl-3-<(methoxycarbonyl)methyl>-2-<(Z)-2-pentenyl>cyclopentanone

(2R*,3S*)-3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanone

diazomethane

jasmonic acid

Downstream raw materials:

jasmonic acid

methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate

methyl jasmonate

(+/-)-tetrahydrodicranenone

Refernces

• 1、 Torii,S. et al.. "-". . p. 3473 - 3477. Retrieved 1977.
• 2、 Montforts, Franz-Peter,Gesing-Zibulak, Ingrid,Grammenos, Wassilios,Schneider, Manfred,Laumen, Kurt. "Methyl-jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatuerlichen Enantiomer via Palladium(0)-induzierte, enantiodivergente Alkylierung von Cyclopent-2-en-1,3-diol-Derivaten". . p. 1852 - 1859. Retrieved 1989.
• 3、 Busato,Scheffold. "Vitamin-B12-catalyzed C,C-bond formation: Synthesis of jasmonates via sequential radical reaction". . p. 92 - 99. Retrieved 1994.
• 4、 Kerr, William J.,McLaughlin, Mark,Pauson, Peter L.. "Behaviour of monocomplexed 1,4-diynes in the Khand reaction and use of ethylene equivalent techniques in a convenient route to tritium-labelled methyl jasmonate". . p. 118 - 124. Retrieved 2007/10/03.
• 5、 Hailes, Helen C,Isaac, Ben,Hashim Javaid. "Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one". . p. 10329 - 10333. Retrieved 2007/10/03.