Methyl hex-4-enoate

Base Information

• Chemical Name: Methyl hex-4-enoate
• CAS No.: 2396-79-4
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• DSSTox Substance ID: DTXSID60930258
• Mol file: 2396-79-4.mol

Synonyms:13894-60-5;METHYL HEX-4-ENOATE;DTXSID60930258

Chemical Property of Methyl hex-4-enoate

Chemical Property:

• PSA: 26.30000
• LogP: 1.51570
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CCCC(=O)OC

Technology Process of Methyl hex-4-enoate

There total 4 articles about Methyl hex-4-enoate 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: 77.0%

hex-4-enoic acid (35194-36-6) + methyl iodide (74-88-4) → E,Z-4-hexenecarboxylic acid methyl ester (2396-79-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/chem.200601685

Reference yield: 72.0%

bis(methylacrylate)(pyridine)nickel(0) (126031-41-2) + 1-bromo-1-propene (590-14-7) → E,Z-4-hexenecarboxylic acid methyl ester (2396-79-4)

Guidance literature:

With water; In tetrahydrofuran; water; byproducts: Ni(OH)Br, CH2CHCOOCH3, C5H5N; addn. of degassed water to a soln. of Ni-complex; stirring vigorously at room temp.; addn. of propene-compound; centrifugation; distn. of residual soln.; addn. of NiCl2*2H2O to remove pyridine; sublimation (vac.);

DOI:10.1016/0022-328X(89)85119-8

Reference yield:

methyl 3-hexenoate (2396-78-3) → methyl 2-hexenoate (2396-77-2) + E,Z-4-hexenecarboxylic acid methyl ester (2396-79-4)

Guidance literature:

With acetylacetonatodicarbonylrhodium(l); carbon monoxide; hydrogen; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); In toluene; at 90 ℃; for 16h; under 11251.1 Torr; Autoclave;

DOI:10.1021/acscatal.7b00249

upstream raw materials:

hex-4-enoic acid

methyl iodide

bis(methylacrylate)(pyridine)nickel⁽⁰⁾

1-bromo-1-propene

Downstream raw materials:

N-phenylhex-4-enamide

hex-4-enoic acid

Refernces

• 1、 Brentzel, Zachary J.,Ball, Madelyn R.,Dumesic, James A.. "Selective Production of Terminally Unsaturated Methyl Esters from Lactones Over Metal Oxide Catalysts". . p. 3072 - 3081. Retrieved 2018/08/22.
• 2、 Aldegunde, Maria J.,Garcia-Fandino, Rebeca,Castedo, Luis,Granja, Juan R.. "Dienyne ring-closing metathesis approach for the construction of taxosteroids". . p. 5135 - 5150. Retrieved 2008/02/11.