cis-7,8-Epoxy-2-methyloctadecane

Base Information

• Chemical Name: cis-7,8-Epoxy-2-methyloctadecane
• CAS No.: 29804-22-6
• Deprecated CAS: 57457-72-4,99130-43-5,99130-43-5
• Molecular Formula: C₁₉H₃₈O
• Molecular Weight: 282.51
• European Community (EC) Number: 249-861-6,260-747-5
• UNII: E5FWS893X3,1FU18G2315
• DSSTox Substance ID: DTXSID4035548
• Nikkaji Number: J57.956D
• Wikipedia: Disparlure
• Wikidata: Q1229127
• Metabolomics Workbench ID: 5649
• Mol file: 29804-22-6.mol

Synonyms:2-methyl-7,8-epoxyoctadecane;disparlure;disparlure, (2R)-(cis)-isomer;disparlure, (2R)-(trans)-isomer;disparlure, (2S)-(cis)-isomer;disparlure, (2S)-(trans)-isomer;disparlure, (cis)-(+-)-isomer;disparlure, (cis)-isomer;disparlure, (trans)-isomer

Chemical Property of cis-7,8-Epoxy-2-methyloctadecane

Chemical Property:

• Vapor Pressure: 0.000168mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 340.6°Cat760mmHg
• Flash Point: 139.7°C
• PSA: 12.53000
• Density: 0.844g/cm³
• LogP: 6.50100
• Storage Temp.: 2-8°C
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 282.292265831
• Heavy Atom Count: 20
• Complexity: 212

Purity/Quality:

99%, ^*data from raw suppliers

(±)-Disparlure ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC1C(O1)CCCCC(C)C
• Isomeric SMILES: CCCCCCCCCC[C@@H]1[C@@H](O1)CCCCC(C)C
• Uses: (±)-Disparlure can be utilized in agricultural use and biological study for pheromone preparations containing disparlure and monachalure for control of Lymantria insect pests in forest tree cultures.

Technology Process of cis-7,8-Epoxy-2-methyloctadecane

There total 40 articles about cis-7,8-Epoxy-2-methyloctadecane 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: 91.0%

cis-2-Methyl-7-octadecen (35354-39-3) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1055/s-1983-30302

Reference yield:

trans-7,8-epoxy-2-methyloctadecane (51050-50-1) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4) + trans-7,8-epoxy-2-methyloctadecane (42991-03-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Title compound not separated from byproducts;

DOI:10.1016/0022-328X(85)87361-7

Reference yield:

2-methyloctadec-7-yne (35354-38-2) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Lindlar / ethanol / Ambient temperature

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

With hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In ethanol; dichloromethane;

upstream raw materials:

cis-2-Methyl-7-octadecen

4-methylpentyllithium

(3-decyloxiran-2-yl)methyl 4-methylbenzenesulfonate

trans-7,8-epoxy-2-methyloctadecane

Refernces

• 1、 -. "SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES". Paragraph 0212; 0213. . Retrieved 2013/09/12.
• 2、 Bykov,Goletiani,Butenko,Finkel'shtein. "Stereoselective cometathesis of 1,5-cyclooctadiene with ethylene as an efficient pathway to Z-ene biologically active natural products". . p. 163 - 166. Retrieved 2007/10/03.