Methyl (Z)-4-decenoate

Base Information

• Chemical Name: Methyl (Z)-4-decenoate
• CAS No.: 7367-83-1
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• European Community (EC) Number: 230-914-7
• UNII: 0KBW80KW5K
• DSSTox Substance ID: DTXSID60864044
• Nikkaji Number: J212.365G
• Wikidata: Q27236894
• Metabolomics Workbench ID: 4122
• Mol file: 7367-83-1.mol

Synonyms:Methyl (Z)-4-decenoate;7367-83-1;methyl (Z)-dec-4-enoate;Methyl 4-decenoate;Methyl 4-decenoate, (4Z)-;Methyl cis-4-decenoate;UNII-0KBW80KW5K;4-Decenoic acid, methyl ester, (Z)-;0KBW80KW5K;EINECS 230-914-7;4-Decenoic acid, methylester, (4Z)-;4-Decenoic acid, methyl ester, (4Z)-;WE(1:0/10:1(4Z));METHYL-CIS-4-DECENOATE;formyl 4Z-decenoate;Methyl 4Z-decenoate;(4Z)-methyl 4-decenoate;(4Z)-Methyl dec-4-enoate;Methyl (4Z)-4-decenoate #;DTXSID60864044;CRHITZQXHNFRAZ-FPLPWBNLSA-N;(Z)-4-Decenoic acid methyl ester;METHYL 4-DECENOATE, (Z)-;4-Decenoic acid, methyl ester, Z-;LMFA07010477;AKOS006279439;DECENOIC ACID METHYL ESTER, (Z)-4-;Q27236894

Chemical Property of Methyl (Z)-4-decenoate

Chemical Property:

• Vapor Pressure: 0.138mmHg at 25°C
• Refractive Index: 1.442
• Boiling Point: 216.8 °C at 760 mmHg
• Flash Point: 68.9 °C
• PSA: 26.30000
• Density: 0.889 g/cm³
• LogP: 3.07610
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

METHYL (Z)-4-DECENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\CCC(=O)OC

Technology Process of Methyl (Z)-4-decenoate

There total 6 articles about Methyl (Z)-4-decenoate 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: 95.0%

methanol (67-56-1) + (Z)-dec-4-enoic acid (505-90-8) → (Z)-dec-4-enoic acid methyl ester (7367-83-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1021/jacs.5b04289

Reference yield:

(3-(methoxycarbonyl)propyl)triphenylphosphonium bromide (13395-34-1) + hexanal (66-25-1) → (Z)-dec-4-enoic acid methyl ester (7367-83-1)

Guidance literature:

(3-(methoxycarbonyl)propyl)triphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

hexanal; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1039/c9cc07466j

Reference yield:

(Z)-4-decenal (30390-50-2,65405-70-1,21662-09-9) → (Z)-dec-4-enoic acid methyl ester (7367-83-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Oxone / N,N-dimethyl-formamide / 2 h / 20 °C

2: dicyclohexyl-carbodiimide / dichloromethane / 20 °C

With Oxone; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.5b04289

upstream raw materials:

methanol

(Z)-4-decenoic acid ethyl ester

diazomethane

(Z)-dec-4-enoic acid

Downstream raw materials:

(Z)-dec-4-enoic acid

Refernces

• 1、 Zhang, Chun,Santiago, Celine B.,Kou, Lei,Sigman, Matthew S.. "Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems". supporting information. p. 7290 - 7293. Retrieved 2015/06/30.
• 2、 Roach, Braden,Eisner, Thomas,Meinwald, Jerrold. "Defense Mechanisms of Arthropods. 83. α- and β-Necrodol, Novel Terpenes from a Carrion Beetle (Necrodes surinamensis, Silphidae, Coleoptera)". . p. 4047 - 4051. Retrieved 2007/10/02.