Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate

Base Information

• Chemical Name: Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate
• CAS No.: 62497-24-9
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• DSSTox Substance ID: DTXSID10470816
• Wikidata: Q82298992
• Mol file: 62497-24-9.mol

Synonyms:Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate;62497-24-9;2-Propynoic acid, 3-(3,4-dimethoxyphenyl)-, methyl ester;DTXSID10470816;AKOS013860102;methyl 3-(3,4-dimethoxyphenyl)propynoate

Chemical Property of Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate

Chemical Property:

• PSA: 44.76000
• LogP: 1.22830
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 299

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C#CC(=O)OC)OC

Technology Process of Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate

There total 7 articles about Methyl 3-(3,4-dimethoxyphenyl)prop-2-ynoate 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: 93.0%

2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene (118199-01-2) + methyl chloroformate (79-22-1) → (3,4-dimethoxyphenyl)propynoic acid methyl ester (62497-24-9)

Guidance literature:

2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene; With n-butyllithium; In hexane; at -78 - 0 ℃; for 1.5h;

methyl chloroformate; In hexane; at -78 - 0 ℃; for 1.16667h;

DOI:10.1021/ja052680h

Reference yield: 77.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 3,4-dimethoxy-benzaldehyde (120-14-9) + methyl chloroformate (79-22-1) → (3,4-dimethoxyphenyl)propynoic acid methyl ester (62497-24-9)

Guidance literature:

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; 3,4-dimethoxy-benzaldehyde; With potassium carbonate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl chloroformate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201402803

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (3,4-dimethoxyphenyl)propynoic acid methyl ester (62497-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 88 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: n-BuLi / hexane / 1.5 h / -78 - 0 °C

2.2: 93 percent / hexane / 1.17 h / -78 - 0 °C

With n-butyllithium; triphenylphosphine; In hexane; dichloromethane;

DOI:10.1021/ja052680h

upstream raw materials:

3,4-dimethoxyphenylpropiolic acid

dimethyl sulfate

2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene

methyl chloroformate

Downstream raw materials:

methyl 2-(3,4-dimethoxyphenyl)-4-formyl-7-methoxybenzo[b]furan-3-carboxylate

methyl 4-methyl-7-methoxy-2-(3,4-dimethoxyphenyl)benzo[b]furan-3-carboxylate

methyl 4-hydroxymethyl-7-methoxy-2-(3,4-dimethoxyphenyl)-benzo[b]furan-3-carboxylate

Refernces

• 1、 Hajbi, Youssef,Neagoie, Cléopatra,Biannic, Bérenger,Chilloux, Aurélie,Vedrenne, Emeline,Baldeyrou, Brigitte,Bailly, Christian,Mérour, Jean-Yves,Rosca, Sorin,Routier, Sylvain,Lansiaux, Amélie. "Synthesis and biological activities of new furo[3,4-b]carbazoles: Potential topoisomerase II inhibitors". experimental part. p. 5428 - 5437. Retrieved 2010/12/25.
• 2、 Savechenkov,Vasil'ev,Rudenko. "Oxidation of aromatic compounds: XII. Regio- and stereoselective oxidative dimerization of alkyl 3-arylpropynoates in the system CF3CO 2H-CH2Cl2-PbO2". . p. 1279 - 1283. Retrieved 2007/10/03.