Ethyl (Z)-4-decenoate

Base Information

• Chemical Name: Ethyl (Z)-4-decenoate
• CAS No.: 7367-84-2
• Molecular Formula: C12H22O2
• Molecular Weight: 198.305
• European Community (EC) Number: 230-915-2
• DSSTox Substance ID: DTXSID801314844
• Nikkaji Number: J212.366E
• Mol file: 7367-84-2.mol

Synonyms:Ethyl (Z)-4-decenoate;7367-84-2;ethyl (Z)-dec-4-enoate;4-Decenoic acid, ethyl ester, (Z)-;Ethyl cis-4-decenoate;Ethyl (4Z)-4-decenoate;EINECS 230-915-2;ETHYL (CIS)-4-DECENOATE;(Z)-4-Decenoic acid ethyl ester;AWNIQMQADACLCJ-HJWRWDBZSA-N;DTXSID801314844;AKOS006229459

Chemical Property of Ethyl (Z)-4-decenoate

Chemical Property:

• Vapor Pressure: 0.0465mmHg at 25°C
• Boiling Point: 236.8°Cat760mmHg
• Flash Point: 73.1°C
• Density: 0.886g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

ETHYL (4Z)-DEC-4-ENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl (Z)-4-decenoate

There total 11 articles about Ethyl (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%

ethanol (64-17-5) + (Z)-dec-4-enoic acid (505-90-8) → (Z)-4-decenoic acid ethyl ester (7367-84-2)

Guidance literature:

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

DOI:10.1021/jacs.5b04289

Reference yield: 80.0%

diethyl 2(Z)-octenyl-malonate (77899-12-8) → (Z)-4-decenoic acid ethyl ester (7367-84-2)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; at 140 - 145 ℃; for 8h;

Reference yield:

2-octyn-1-ol (20739-58-6) → (Z)-4-decenoic acid ethyl ester (7367-84-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / Lindlar's catalyst/quinoline / hexane

2: 90 percent / PBr₃, pyridine / diethyl ether / cooled, 30 min, then standing overnight, then reflux, 2 h

3: 70 percent / benzene; dimethylformamide / 16 h / Heating

4: 80 percent / NaCl / H₂O; dimethylsulfoxide / 8 h / 140 - 145 °C

With pyridine; hydrogen; phosphorus tribromide; sodium chloride; quinoline; Lindlar's catalyst; In diethyl ether; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(Z)-1-bromo-1-heptene

ethyl acrylate

diethyl 2(Z)-octenyl-malonate

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide

Downstream raw materials:

(Z)-4-decenal

(Z)-6-heneicosen-11-one

(Z)-4-decen-1-ol

(Z)-dec-4-enoic acid methyl ester

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". . p. 7290 - 7293. Retrieved 2015/06/30.
• 2、 Vig, O. P.,Sharma, M. L.,Verma, N. K.,Malik, Neera. "A New Synthesis of (Z)-Heneicos-6-en-11-one, Sex Pheromone of Douglas Fir Lepidoptera Orgyia pseudotsugata". . p. 950 - 951. Retrieved 2007/10/02.