Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-

Base Information

• Chemical Name: Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-
• CAS No.: 221682-41-3
• Molecular Formula: C12H18O3
• Molecular Weight: 210.26952
• Hs Code.: 2918300090
• Mol file: 221682-41-3.mol

Synonyms:Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-;JasMonic Acid (Mixture of isoMers)

Chemical Property of Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-

Chemical Property:

• Refractive Index: 1.49
• Boiling Point: 358.1±15.0 °C(Predicted)
• PKA: 4.52±0.10(Predicted)
• PSA: 54.37000
• Density: 1.061±0.06 g/cm3(Predicted)
• LogP: 2.41270

Purity/Quality:

98%,99%, ^*data from raw suppliers

JasmonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Jasmonic Acid can be used as pesticides.

Technology Process of Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-

There total 16 articles about Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)- 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:

dicyclohexylamine (Z)-2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate → (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid (221682-41-3)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 0 - 0.15 ℃;

Reference yield:

methyl jasmonate (1101843-02-0) → (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid (221682-41-3)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 3h;

Reference yield:

(Z)-4-heptenoic acid (41653-95-6) → (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid (221682-41-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / SOCl₂, pyridine / diethyl ether / 2 h / Ambient temperature

2: tetrahydrofuran / 2 h / -78 - 20 °C

3: 68 percent / oxalic acid / H₂O / 3 h / Heating

4: 69 percent / NaOH / H₂O; dioxane / 1.5 h / Heating

5: 92 percent / NaH / methanol / 3 h / -10 - -5 °C

6: 1.) 10percent aq. NaOH, 2.) 3percent aq. H₂SO₄ / 1.) overnight, 2.) reflux, 5 h

With pyridine; sodium hydroxide; thionyl chloride; sulfuric acid; oxalic acid; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water;

DOI:10.1246/bcsj.54.505

upstream raw materials:

methyl jasmonate

3--2-(cis-2-pentenyl)cyclopentenone

(Z)-4-heptenoic acid

(Z)-2-(2-pentenyl)-2-cyclopenten-1-one

Downstream raw materials:

methyl jasmonate

Refernces

• 1、 -. "METHODS FOR PREPARATION OF JASMONATE COMPOUNDS". Paragraph 048. . Retrieved 2019/07/20.
• 2、 Sato, Toshio,Kawara, Tatsuo,Sakata, Kazumi,Fujisawa, Tamotsu. "Jasmonoid Synthesis from cis-4-Heptenoic Acid". . p. 505 - 508. Retrieved 2007/10/02.