Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate

Base Information

• Chemical Name: Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate
• CAS No.: 7605-45-0
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• Nikkaji Number: J2.104.095I,J354.535K
• Wikidata: Q63399959
• Mol file: 7605-45-0.mol

Synonyms:Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate;7605-45-0;Cinnamic acid, alpha-methyl-3,4-(methylenedioxy)-, methyl ester;methyl (E)-3-(1,3-benzodioxol-5-yl)-2-methylprop-2-enoate;Q63399959;METHYL (3,4-METHYLENEDIOXY)-ALPHA-METHYLCINNAMATE

Chemical Property of Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate

Chemical Property:

• PSA: 44.76000
• LogP: 1.99160
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1=CC2=C(C=C1)OCO2)C(=O)OC
• Isomeric SMILES: C/C(=C\C1=CC2=C(C=C1)OCO2)/C(=O)OC

Technology Process of Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate

There total 12 articles about Methyl alpha-methyl-3,4-(methylenedioxy)cinnamate 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: 96.0%

methyl 3-hydroxy-2-methylene-3-[(3,4-methylenedioxy)phenyl]propanoate (218934-11-3) → methyl E-3-<3,4-(methylenedioxy)phenyl>-2-methylacrylate (7605-45-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 65 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2004.04.087

Reference yield: 90.0%

methyl (Z)-2-(bromomethyl)-3-(3,4-methylenedioxyphenyl)-2-propenoate (792926-48-8) → methyl E-3-<3,4-(methylenedioxy)phenyl>-2-methylacrylate (7605-45-0)

Guidance literature:

With acetic acid; zinc; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.08.018

Reference yield: 77.0%

1,3-benzodioxol-5-yl → C24H22O8S2 + methyl E-3-<3,4-(methylenedioxy)phenyl>-2-methylacrylate (7605-45-0)

Guidance literature:

1,3-benzodioxol-5-yl; With sodium thiosulfate; In methanol; at 20 ℃;

With samarium; iodine; ammonium chloride; In tetrahydrofuran; at 20 ℃; for 4h; Further stages.;

DOI:10.1055/s-2006-950406

upstream raw materials:

piperonal

propanoic acid methyl ester

1,2-(methylenedioxy)-4-bromobenzene

methacrylic acid methyl ester

Downstream raw materials:

trans-3-(3,4-methylenedioxyphenyl)-2-methylacrylic acid

Refernces

• 1、 Liu, Yunkui,Xu, Danqian,Xu, Zhenyuan,Zhang, Yongmin. "Stereoselective synthesis of trisubstituted alkenes containing (Z)-allylthio units from the acetates of Baylis-Hillman adducts". . p. 188 - 198. Retrieved 2008/09/18.
• 2、 Liu, Yunkui,Mao, Dajie,Xu, Danqian,Xu, Zhenyuan,Zhang, Yongmin. "Sm/HOAc/EtOH system-mediated reduction of Baylis-Hillman acetates". . p. 4389 - 4397. Retrieved 2008/03/14.