Japonilure

Base Information

• Chemical Name: Japonilure
• CAS No.: 64726-91-6
• Deprecated CAS: 111192-53-1,133494-64-1,77518-55-9,133494-64-1,77518-55-9
• Molecular Formula: C14H24O2
• Molecular Weight: 224.343
• Hs Code.: 2932209090
• European Community (EC) Number: 265-035-8
• UNII: S27IJL8RH3
• DSSTox Substance ID: DTXSID2035308
• Nikkaji Number: J307.285A
• Wikidata: Q27288479
• Mol file: 64726-91-6.mol

Synonyms:5-(dec-1-enyl)oxacyclopentan-2-one;japonilure

Chemical Property of Japonilure

Chemical Property:

• Vapor Pressure: 8.67E-05mmHg at 25°C
• Refractive Index: 1.512
• Boiling Point: 340.3 °C at 760 mmHg
• Flash Point: 141.3 °C
• PSA: 26.30000
• Density: 0.985 g/cm³
• LogP: 3.99880
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 224.177630004
• Heavy Atom Count: 16
• Complexity: 221

Purity/Quality:

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

JAPONILURE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CC1CCC(=O)O1
• Isomeric SMILES: CCCCCCCC/C=C\[C@H]1CCC(=O)O1

Technology Process of Japonilure

There total 66 articles about Japonilure 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: 94.0%

(R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one (72151-69-0) → japonilure (64726-91-6)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In pentane; at 0 ℃; for 4h;

DOI:10.1021/ol016986e

Reference yield: 80.0%

(R,Z)-methyl 4-hydroxytetradec-5-enoate → japonilure (64726-91-6)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.09.008

Reference yield:

1-decyne (764-93-2) → japonilure (64726-91-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.25 h / -78 °C

1.2: 97 percent / tetrahydrofuran / 18 h / 20 - 25 °C

2.1: 89 percent / hydrogen peroxide; aq. sodium hydroxide / diethyl ether / 2 h / 25 °C

3.1: 69 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / 100 °C

4.1: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr

With sodium hydroxide; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0022-328X(00)00595-7

upstream raw materials:

(R)-tetrahydro-5-oxo-2-furancarbaldehyde

(S)-5-<(Z)-dec-1-enyl>dihydrofuran-2(3H)-one

methyl 4-oxo-5-tetradecyonate

4-Hydroxy-tetradec-5-ynoic acid

Refernces

• 1、 Fukusaki, Eiichiro,Senda, Shuji,Nakazono, Yutaka,Omata, Tetsuo. "LIPASE-CATALYZED KINETIC RESOLUTION OF METHYL 4-HYDROXY-5-TETRADECYNOATE AND ITS APPLICATION TO A FACILE SYNTHESIS OF JAPANESE BEETLE PHEROMONE". . p. 6223 - 6230. Retrieved 1991.
• 2、 Xu, Hao,Li, Shuo-Ning,Yang, Yan-Qing,Zhou, Yun,Yang, Qian-Zhen,Bian, Qing-Hua,Zhong, Jiang-Chun,Wang, Min. "Catalytic asymmetric synthesis of Japonilure and its enantiomer". . p. 1372 - 1375. Retrieved 2015/01/16.
• 3、 Papillon, Julien P. N.,Taylor, Richard J. K.. "The preparation of nonracemic secondary α-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols". . p. 119 - 122. Retrieved 2007/10/03.