2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester

Base Information

• Chemical Name: 2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester
• CAS No.: 13058-12-3
• Molecular Formula: C12H20 O2
• Molecular Weight: 196.29
• Nikkaji Number: J354.769H
• Mol file: 13058-12-3.mol

Synonyms:Ethyl nerate;2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester;ZPKNTCZTABQJPS-LUAWRHEFSA-N;(Z)-ETHYL 3,7-DIMETHYL-2,6-OCTADIENOATE;(Z)-3,7-Dimethyl-2,6-octadienoic acid ethyl ester

Chemical Property of 2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester

Chemical Property:

• Vapor Pressure: 0.00881mmHg at 25°C
• Boiling Point: 266.1°Cat760mmHg
• Flash Point: 119.8°C
• PSA: 26.30000
• Density: 0.904g/cm³
• LogP: 3.24220
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

ETHYL GERANATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)CCC=C(C)C
• Isomeric SMILES: CCOC(=O)/C=C(/C)\CCC=C(C)C

Technology Process of 2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester

There total 20 articles about 2,6-Octadienoic acid, 3,7-dimethyl-, ethyl ester 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: 88.0%

α-sulfinyl citronellate (79858-00-7) → ethyl 3,7-dimethyl-2,6-octadienoate (13058-12-3)

Guidance literature:

With calcium carbonate; In toluene; for 7h; Heating;

DOI:10.1246/cl.1981.1159

Reference yield: 85.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) → ethyl 3,7-dimethyl-2,6-octadienoate (13058-12-3)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In 1,2-dimethoxyethane; at 0 ℃; for 0.25h;

6-Methyl-hept-5-en-2-on; In 1,2-dimethoxyethane; for 4h; Heating;

DOI:10.1081/SCC-120017196

Reference yield: 50.0%

(E)-3,7-Dimethyl-6-phenylsulfanyl-octa-2,7-dienoic acid ethyl ester (112157-80-9) → ethyl 3,7-dimethyl-2,6-octadienoate (13058-12-3)

Guidance literature:

With hexacarbonyl molybdenum; water; In 1,4-dioxane; for 3h;

DOI:10.1246/bcsj.62.2913

upstream raw materials:

1-Ethoxy-3,7-dimethyloct-6-en-1-yn-3-ol

diethoxyphosphoryl-acetic acid ethyl ester

6-Methyl-hept-5-en-2-on

ethyl 4-bromo-3-methylcrotonate

Downstream raw materials:

geraniol

Nerol

Geraniol

(E/Z)-3,7-dimethyl-2,6-octadienal

Refernces

• 1、 Tanaka,K. et al.. "-". . p. 471 - 474. Retrieved 1977.
• 2、 Cabré, Albert,Gar?on, Martí,Gallen, Albert,Grisoni, Lorenzo,Grabulosa, Arnald,Verdaguer, Xavier,Riera, Antoni. "Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols Using MaxPHOX Ligands: Experimental and Theoretical Study". . p. 4112 - 4120. Retrieved 2020/07/04.
• 3、 Rabe, Patrick,Barra, Lena,Rinkel, Jan,Riclea, Ramona,Citron, Christian A.,Klapschinski, Tim A.,Janusko, Aron,Dickschat, Jeroen S.. "Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by 13C-Labeling Experiments". supporting information. p. 13448 - 13451. Retrieved 2015/11/09.