Sinapyl p-coumarate

Base Information

• Chemical Name: Sinapyl p-coumarate
• CAS No.: 186023-58-5
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• DSSTox Substance ID: DTXSID101121616
• Nikkaji Number: J782.466A,J2.660.001D
• Metabolomics Workbench ID: 70798
• Mol file: 186023-58-5.mol

Synonyms:Sinapyl p-coumarate;bmse010318;SureCN10054941;SCHEMBL10054941;DTXSID101121616;(E)-3-(4-Hydroxyphenyl)propenoic acid 4-hydroxy-3,5-dimethoxycinnamyl ester;[(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)allyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate;(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propen-1-yl (2E)-3-(4-hydroxyphenyl)-2-propenoate;186023-58-5

Chemical Property of Sinapyl p-coumarate

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 356.12598835
• Heavy Atom Count: 26
• Complexity: 467

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=CCOC(=O)C=CC2=CC=C(C=C2)O
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)/C=C/COC(=O)/C=C/C2=CC=C(C=C2)O

Technology Process of Sinapyl p-coumarate

There total 8 articles about Sinapyl p-coumarate 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: 94.0%

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3,5-dimethoxy-phenyl)-allyl ester (213185-31-0) → (E)-3-(4-Hydroxy-phenyl)-acrylic acid (E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-allyl ester (186023-58-5)

Guidance literature:

With pyrrolidine;

DOI:10.1021/jf980440y

Reference yield:

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-[4-(2,4-dinitro-phenoxy)-3,5-dimethoxy-phenyl]-allyl ester (186023-57-4) → (E)-3-(4-Hydroxy-phenyl)-acrylic acid (E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-allyl ester (186023-58-5)

Guidance literature:

With piperazine; In tetrahydrofuran; for 2h; Yield given; Ambient temperature;

DOI:10.1016/S0031-9422(96)00431-1

Reference yield:

(E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate (71686-40-3) → (E)-3-(4-Hydroxy-phenyl)-acrylic acid (E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-allyl ester (186023-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94.5 percent / (CH₃)3CNH₂*BH₃ / CH₂Cl₂ / 2 h / Ambient temperature

2: 80 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h

3: 94 percent / pyrrolidine

With pyrrolidine; dmap; N-tert-butylaminoborane; triethylamine; In dichloromethane;

DOI:10.1021/jf980440y

upstream raw materials:

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-[4-(2,4-dinitro-phenoxy)-3,5-dimethoxy-phenyl]-allyl ester

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-3-(4-acetoxy-3,5-dimethoxy-phenyl)-allyl ester

(E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate

p-acetoxycinnamoyl chloride