(+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid

Base Information

• Chemical Name: (+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid
• CAS No.: 131488-83-0
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.289
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID60403639
• Wikidata: Q82207361
• Mol file: 131488-83-0.mol

Synonyms:(+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid;131488-83-0;2-(3-hydroxy-2-pent-2-enylcyclopentyl)acetic acid;DTXSID60403639;FT-0640516

Chemical Property of (+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid

Chemical Property:

• Refractive Index: 1.517
• PSA: 57.53000
• LogP: 2.20450
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 212.14124450
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

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

(±)-Cucurbicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1C(CCC1O)CC(=O)O

Technology Process of (+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid

There total 43 articles about (+/-)-3-Hydroxy-2-(2-pentenyl)cyclopentaneacetic Acid 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:

(1S,5S,8R)-8-<(2'Z)-pent-2'-enyl>-2-oxybicyclo<3.2.1>octan-3-on (128820-28-0,807630-26-8) → [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid (34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4)

Guidance literature:

With potassium hydroxide; water; In methanol; at 20 ℃; for 2h;

DOI:10.1080/00397919708004999

Reference yield:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid (34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / benzene / 0.5 h / 20 °C

2: 71 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

3: 90 percent / H₂ / Rh-Al₂O₃ / ethanol / 760 Torr

4: 98 percent / NaOH; water / methanol / 3 h / 20 °C

5: 70 percent / iodobenzene diacetate; iodine / benzene / 12.75 h / Heating; two 100W tungsten filament lamps

6: NaIO₄ / RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 12 h

7: 426 mg / benzene; methanol; hexane / 0.5 h / 20 °C

8: 410 mg / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

9: 240 mg / KN(TMS)2 / tetrahydrofuran / -78 - 0 °C

10: KOH; water / methanol / 2 h / 20 °C

With potassium hydroxide; sodium hydroxide; sodium periodate; [bis(acetoxy)iodo]benzene; water; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; ruthenium trichloride; rhodium on alumina; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; water; acetonitrile; benzene; 1: Wittig reaction / 2: Elimination / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: oxidative decarboxylation / 6: Catalytic oxidation / 7: Methylation / 8: Reduction / 9: Wittig reaction / 10: Hydrolysis;

DOI:10.1080/00397919708004999

Reference yield:

(1S,5R)-6-(2'-iodoethyl)-2-oxabicyclo[3.3.0]-oct-3-one (194141-90-7) → [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid (34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1: NaIO₄ / RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 12 h

2: 426 mg / benzene; methanol; hexane / 0.5 h / 20 °C

3: 410 mg / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

4: 240 mg / KN(TMS)2 / tetrahydrofuran / -78 - 0 °C

5: KOH; water / methanol / 2 h / 20 °C

With potassium hydroxide; sodium periodate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; hexane; water; acetonitrile; benzene; 1: Catalytic oxidation / 2: Methylation / 3: Reduction / 4: Wittig reaction / 5: Hydrolysis;

DOI:10.1080/00397919708004999

upstream raw materials:

n-propyltriphenylphosphonium bromide

((3aR,4S,6aS)-2-Hydroxy-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid

<1R*,2S*,3R*>-1-Hydroxy-2-<(3Z)-pentenyl>-3-cyanomethylcyclopentane

[(1R,2S,3S)-3-Acetoxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid methyl ester

Downstream raw materials:

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

(+/-)-Cucurbic acid

(+/-)-methyl trans-dihydrojasmonate

(+/-)-methyl dihydroepijasmonate

Refernces

• 1、 Kitahara, Takeshi,Warita, Yasuhiro,Abe, Masaki,Seya, Motohide,Takagi, Yoshikazu,Mori, Kenji. "Stereoselective Synthesis of Methyl Epijasmonate". . p. 1013 - 1017. Retrieved 2007/10/02.
• 2、 Seto, Hideharu,Yoshioka, Hirosuke. "An Efficient and Stereocontrolled Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Cucurbic Acid". . p. 1797 - 1800. Retrieved 2007/10/02.