Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate

Base Information

• Chemical Name: Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate
• CAS No.: 2630-39-9
• Deprecated CAS: 29852-02-6,80450-69-7
• Molecular Formula: C13H22O3
• Molecular Weight: 226.316
• Hs Code.: 2918300090
• European Community (EC) Number: 220-112-5
• UNII: XM1C2C5MMN
• DSSTox Substance ID: DTXSID80883873
• Nikkaji Number: J192.149E
• Wikidata: Q27889465
• Mol file: 2630-39-9.mol

Synonyms:2630-39-9;trans-(-)-Hedione;Dihydrojasmonic acid methyl ester;Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate;(-)-Methyl dihydrojasmonate;Methyl trans-dihydrojasmonate;(1R,2R)-Methyl dihydrojasmonate;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1R,2R)-;UNII-XM1C2C5MMN;XM1C2C5MMN;methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate;EINECS 220-112-5;Methyl dihydrojasmonate, (-)-trans-;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (-)-;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1R-trans)-;Methyldihydrojasmonate;methyl 2-((1R,2R)-3-oxo-2-pentylcyclopentyl)acetate;Hedion;methyl hydrojasmonate;HEDIONE HC;Methyl (Z)-dihydrojasmonate;Methyl (1R- trans)- 3- oxo- 2- pentylcyclopentaneacetate;Methyldihydro jasmonate (cis);SCHEMBL2120759;CHEBI:89741;FEMA 3408;DTXSID80883873;KVWWIYGFBYDJQC-GHMZBOCLSA-N;trans-(-)-methyl dihydrojasmonate;MFCD00151188;AKOS015903466;METHYL DIHYDROJASMONATE (NATURAL);(-)-TRANS-METHYL DIHYDROJASMONATE;FEMA NO. 3408, (-)-TRANS-;METHYL DIHYDROJASMONATE, TRANS-(-)-;METHYL DIHYDROJASMONATE (-)-(1R,2R)-FORM;Q27889465;METHYL DIHYDROJASMONATE (-)-(1R,2R)-FORM [MI];Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1theta-trans)-;CYCLOPENTANEACETICACID, 3-OXO-2-PENTYL-, METHYL ESTER, (1R,2R)-;29852-02-6

Chemical Property of Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate

Chemical Property:

• Vapor Pressure: 0.00071mmHg at 25°C
• Refractive Index: 1.453
• Boiling Point: 307.755 °C at 760 mmHg
• Flash Point: 130.816 °C
• PSA: 43.37000
• Density: 0.984 g/cm³
• LogP: 2.72510
• 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%, ^*data from raw suppliers

(-)MethylDihydrojasmonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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 Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate

There total 70 articles about Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate 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:

(+/-)-δ-decanolactone (705-86-2) → 5(6)-decenoic acid (85392-03-6) + 5-hexyldihydro-2(3H)-furanone (706-14-9,2825-92-5) + 6-decenoic acid (85392-04-7) + 4-decenoic acid (26303-90-2)

Guidance literature:

With active clay; at 170 ℃; for 5h;

DOI:10.1271/bbb.69.2416

Reference yield:

(+)-methyl (1R,2S,3R)-2,3-epoxy-2-pentyl-1-cyclopentaneacetate (207513-80-2) → <2S*,3R*>-3-methoxycarbonylmethyl-2-pentylcyclopentanone(methyl dihydroepijasmonate) (39647-11-5,128087-96-7) + methyl dihydro jasmonate (2630-39-9,128087-96-7)

Guidance literature:

With aluminium trichloride; In toluene; at 4 - 7 ℃; for 0.25h; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(20000204)39:3<569::AID-ANIE569>3.0.CO;2-8

Reference yield:

(+)-methyl (1R,2S,3R)-2,3-epoxy-2-pentyl-1-cyclopentaneacetate (207513-80-2) → <2S*,3R*>-3-methoxycarbonylmethyl-2-pentylcyclopentanone(methyl dihydroepijasmonate) (39647-11-5,128087-96-7) + methyl dihydro jasmonate (2630-39-9,128087-96-7) + methyl (2E)-2-(2-pentylcyclopent-2-en-1-ylidene)acetate

Guidance literature:

With boron trifluoride diethyl etherate; sodium carbonate; In toluene; at 2 - 5 ℃; for 0.0333333h; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(20000204)39:3<569::AID-ANIE569>3.0.CO;2-8

upstream raw materials:

diazomethane

(-)-9,10-dihydrojasmonic acid

methyl 2-(3-hydroxy-2-pentylcyclopentyl)acetate

(+)-4,5-didehydro methyl epijasmonate

Downstream raw materials:

(+/-)-methyl trans-dihydrojasmonate

dihydro-cis-jasmone

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

Refernces

• 1、 Ito, Nobuhiko,Wada, Shigeru,Yamanaka, Yousuke,Takagaki, Hitoshi,Nakamura, Hironori. "Identification of novel decenoic acids in heated butter". . p. 2416 - 2420. Retrieved 2008/02/03.
• 2、 Krause, Norbert,Ebert, Sophia. "Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation". . p. 3837 - 3841. Retrieved 2007/10/03.