(Z)-3-Pentenoic acid, methyl ester

Base Information

• Chemical Name: (Z)-3-Pentenoic acid, methyl ester
• CAS No.: 36781-66-5
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• DSSTox Substance ID: DTXSID201312890
• Nikkaji Number: J746.755I
• Mol file: 36781-66-5.mol

Synonyms:(Z)-3-Pentenoic acid, methyl ester;(Z)-CH3CH=CHCH2C(O)OCH3;36781-66-5;methyl (Z)-pent-3-enoate;methyl cis-3-pentenoate;Methyl (3Z)-3-pentenoate;Methyl (3Z)-3-pentenoate #;SCHEMBL5834646;KJALUUCEMMPKAC-ARJAWSKDSA-N;DTXSID201312890;(Z)-3-Pentenoic acid methyl ester

Chemical Property of (Z)-3-Pentenoic acid, methyl ester

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 94.7

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (Z)-3-Pentenoic acid, methyl ester

There total 45 articles about (Z)-3-Pentenoic acid, methyl 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: 87.6%

π-crotyl palladium chloride (35037-11-7) + Methyl formate (107-31-3) → methyl (E)-pent-3-enoate (818-58-6) + methyl 2-methyl-3-butenoate (51747-33-2) + cis-3-pentenoic acid methyl ester (36781-66-5) + palladium (7440-05-3)

Guidance literature:

With carbon monoxide; sodium butyrate; In neat (no solvent); mixt. of PdCl(C3H5), HCO2Me, Na butyrate (as nucleophile) stirred at room temp. for 30 min, addn. of CO, react. time 2 h; react. mixt. filtered, colourless liquid analysed by GLC;

DOI:10.1016/0304-5102(89)80136-1

Reference yield: 41.3%

methanol (67-56-1) + π-crotyl palladium chloride (35037-11-7) → methyl (E)-pent-3-enoate (818-58-6) + methyl 2-methyl-3-butenoate (51747-33-2) + cis-3-pentenoic acid methyl ester (36781-66-5) + palladium (7440-05-3)

Guidance literature:

With carbon monoxide; sodium butyrate; In neat (no solvent); mixt. of PdCl(C3H5), MeOH, Na butyrate (as nucleophile) stirred at room temp. for 30 min, addn. of CO, react. time 2 h; react. mixt. filtered, colourless liquid analysed by GLC;

DOI:10.1016/0304-5102(89)80136-1

Reference yield:

5-bromovaleric acid methyl ester (5454-83-1) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + Methyl 4-pentenoate (818-57-5) + methyl bromide (74-83-9) + methyl 2-pentenoate (15790-87-1,15790-88-2,818-59-7) + methyl 3-pentenoate (20515-19-9,36781-66-5,818-58-6)

Guidance literature:

at 405.2 - 418.8 ℃; Product distribution; Kinetics; Thermodynamic data; pyrolysis, Ea;

DOI:10.1021/j100291a041

upstream raw materials:

methanol

6-oxabicyclo[3.1.0]hex-2-ene

crotylamine

carbon monoxide

Downstream raw materials:

aristolindiquinone

methyl 6-oxohexanoate

hexanedioic acid dimethyl ester

methyl valerate

Refernces

• 1、 Aitipamula, Srinivasulu,Britovsek, George J. P.,Nobbs, James D.,Tay, Dillon W. P.,Van Meurs, Martin. "Directing Selectivity to Aldehydes, Alcohols, or Esters with Diphobane Ligands in Pd-Catalyzed Alkene Carbonylations". . p. 1914 - 1925. Retrieved 2021/06/28.
• 2、 Han, Li-Jun,Ma, Shuang-Shuang,Rao, Chong-Shun,Sheng, Gui-Yang,Xu, Bao-Hua,Zhang, Jun-Ping. "Palladium-Catalyzed Methoxycarbonylation of 1,3-Butadiene to Methyl-3-Pentenoate: Introduction of a Continuous Process". . p. 283 - 290. Retrieved 2021/10/27.