Methyl dihydrojasmonate, (+-)-trans-

Base Information

• Chemical Name: Methyl dihydrojasmonate, (+-)-trans-
• CAS No.: 151716-36-8
• Molecular Formula: C13H22 O3
• Molecular Weight: 226.316
• UNII: 6F0IU8Y5DL,43CCU17TXN
• DSSTox Substance ID: DTXSID40164857
• Nikkaji Number: J1.438.708K
• Wikidata: Q27264763
• Mol file: 151716-36-8.mol

Synonyms:Methyl dihydrojasmonate, (+-)-trans-;UNII-6F0IU8Y5DL;151716-36-8;6F0IU8Y5DL;Methyl (+-)-dihydrojasmonate;FEMA No. 3408, (+-)-trans-;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S,2S)-;Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1S-trans)-;Methyl dihydrojasmonate, trans-(+)-;methyl 2-[(1S,2S)-3-oxo-2-pentylcyclopentyl]acetate;TRANS-HEDIONE;43CCU17TXN;(+)-methyldihydroepijasmonate;(+)-Methyl dihydroepijasmonate;methyl dihydrojasmonate (trans);SCHEMBL17517758;METHYL DL-DIHYDROJASMONATE;DTXSID40164857;KVWWIYGFBYDJQC-QWRGUYRKSA-N;trans-(+)-methyl dihydrojasmonate;METHYL (+)-DIHYDROJASMONATE;(+/-)-METHYL DIHYDROJASMONATE;(+)-trans- Dihydrojasmonic acid methyl;FEMA NO. 3408, (+)-TRANS-;METHYL DIHYDROJASMONATE, TRANS-(+/-)-;(+/-)-DIHYDROJASMONIC ACID METHYL ESTER;METHYL DIHYDROJASMONATE (+)-(1S,2S)-FORM;Q27264763;METHYL DIHYDROJASMONATE (+)-(1S,2S)-FORM [MI];Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1R,2R)-rel-;CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, TRANS-;CYCLOPENTANEACETIC ACID, 3-OXO-2-PENTYL-, METHYL ESTER, TRANS-(+/-)-;2570-03-8

Chemical Property of Methyl dihydrojasmonate, (+-)-trans-

Chemical Property:

• Vapor Pressure: 0.00071mmHg at 25°C
• Refractive Index: 1.453
• Boiling Point: 307.8°C at 760 mmHg
• Flash Point: 130.8°C
• PSA: 43.37000
• Density: 0.984g/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

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
• Uses: Fragrance ingredient in perfumes, toilette and laundry products. Flavor ingredient producing fruit, tea, tobacco, and floral flavors.

Technology Process of Methyl dihydrojasmonate, (+-)-trans-

There total 15 articles about Methyl dihydrojasmonate, (+-)-trans- 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: 98.0%

((1S,2S)-3-Oxo-2-pent-2-ynyl-cyclopentyl)-acetic acid methyl ester → (3S,7S)-methyl jasmonate (78609-06-0) + trans-methyl ((1S,2S)-2-pentyl-3-oxocyclopentyl)acetate (151716-36-8,128087-96-7)

Guidance literature:

With hydrogen; In methanol; at 40 ℃; for 8h; under 760.051 Torr;

DOI:10.1002/anie.201207845

Reference yield:

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate (51806-23-6) → methyl dihydro jasmonate (2630-39-9,128087-96-7) + trans-methyl ((1S,2S)-2-pentyl-3-oxocyclopentyl)acetate (151716-36-8,128087-96-7)

Guidance literature:

With water; In dimethyl sulfoxide; at 190 ℃; for 5h; Title compound not separated from byproducts.;

DOI:10.1021/ol006207e

Reference yield:

methanol (67-56-1) + (2S,3S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-2-pentyl-cyclopentanone → trans-methyl ((1S,2S)-2-pentyl-3-oxocyclopentyl)acetate (151716-36-8,128087-96-7)

Guidance literature:

With sodium hydroxide; ozone; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(01)01437-X

upstream raw materials:

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate

methanol

2-pentyl-2-cyclopenten-1-one

(Z)-methyl 2-(3-oxo-2-pentylidenecyclopentyl)acetate

Refernces

• 1、 Mitsudome, Takato,Takahashi, Yusuke,Ichikawa, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Metal-ligand core-shell nanocomposite catalysts for the selective semihydrogenation of alkynes". supporting information. p. 1481 - 1485. Retrieved 2013/04/10.
• 2、 Hailes, Helen C.,Isaac, Ben,Javaid. "1,4-Addition of chiral 2-propenylphosphonamide anions to α-substituted cyclopentenones: Use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates". . p. 7325 - 7328. Retrieved 2007/10/03.