2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl ester

Base Information

• Chemical Name: 2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl ester
• CAS No.: 132465-10-2
• Molecular Formula: C16H13 N O4 S
• Molecular Weight: 315.34
• DSSTox Substance ID: DTXSID80927701
• Wikidata: Q27185968
• Mol file: 132465-10-2.mol

Synonyms:DTXSID80927701;HMS3266F07;PD043613;Q27185968;2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl ester

Chemical Property of 2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl ester

Chemical Property:

• PSA: 118.79000
• LogP: 2.85218
• Storage Temp.: Desiccate at +4°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 315.05652907
• Heavy Atom Count: 22
• Complexity: 470

Purity/Quality:

99% ^*data from raw suppliers

2-TEDC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)CCOC(=O)C(=CC2=CC(=C(C=C2)O)O)C#N
• Uses: 2-TEDC (cas# 132465-10-2) is a reagent in the preparation of caffeic acid derivatives with potent inhibitory activities on 12-?lipoxygenase.

Technology Process of 2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl ester

There total 3 articles about 2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-thiophen-2-ylethyl 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:

Cyano-acetic acid 2-thiophen-2-yl-ethyl ester (132465-20-4) + 3,4-dihydroxybenzaldehyde (139-85-5) → 2-(2-thienyl)ethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate (132465-10-2)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; benzene; Heating;

DOI:10.1021/jm00108a039

Reference yield:

2-thiophenethanol (5402-55-1) → 2-(2-thienyl)ethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate (132465-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 4-dimethylpyridine (DMAP) / dimethylformamide / 18 h / Ambient temperature

2: piperidine / benzene; dimethylformamide / 24 h / Heating

With piperidine; 4-dimethylpyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.39.3341

Reference yield:

→ 2-(2-thienyl)ethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate (132465-10-2)

Guidance literature:

upstream raw materials:

Cyano-acetic acid 2-thiophen-2-yl-ethyl ester

3,4-dihydroxybenzaldehyde

2-thiophenethanol