20767-04-8

Basic information

• Product Name: 2-Propenoic acid, 3-(3,5-dimethoxyphenyl)-, (2E)-
• Synonyms: 3,5-dimethoxycinnamamic acid;EINECS 240-956-8;3',5'-Dimethoxycinnamic acid;trans-3,5-dimethoxycinnamic acid;Cinnamic acid, 3,5-dimethoxy-, (E)-
• CAS NO: 20767-04-8
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Mol File: 20767-04-8.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(3,5-dimethoxyphenyl)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(3,5-dimethoxyphenyl)-, (2E)-(20767-04-8)
• EPA Substance Registry System: 2-Propenoic acid, 3-(3,5-dimethoxyphenyl)-, (2E)-(20767-04-8)

Safety Data

• Hazardous Substances Data: 20767-04-8(Hazardous Substances Data)

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 64-19-7 acetic acid 
• 42174-79-8 (E)-ethyl 3-(3,5-dimethoxyphenyl)acrylate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 110-89-4 piperidine 
• 108-24-7 acetic anhydride 
• 141-82-2 malonic acid 

Downstream Products

• 1027389-46-3 (E)-N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3,5-dimethoxy-phenyl)-acrylamide 
• 717-94-2 3-(3,5-dimethoxyphenyl)propionic acid 
• 127791-54-2 (2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid 
• 1000895-53-3 5-[2-(3,5-dimethoxy-phenyl)-ethyl]-1H-pyrazol-3-ylamine 
• 959223-70-2 (E)-N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3,5-dimethoxy-phenyl)-acrylamide 
• 29584-65-4 methyl (E)-3-[3,5-dimethoxyphenyl]-2-propenoate 
• 149242-85-3 trans-3,5-dimethoxycinnamic acyl azide 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 

Relevant articles and documents

Dihydroxylation Studies of Isoquinolinones: Synthesis of the EF-Ring of Lysolipin i

Inspired by the potent polycyclic xanthone antibiotic lysolipin I, a general study on asymmetric dihydroxylation reactions of variously substituted isoquinolinones was performed. Different isoquinolinones were efficiently prepared, either by a Pomeranz-Fritsch type condensation or a Curtius rearrangement. Under a broad variety of conventional oxygenation procedures, they proved very unreactive. However, either by suitable substitution of the appending aromatic ring or more forcing conditions a dihydroxylation could finally be performed, which allowed the synthesis of the EF-ring of lysolipin I.

Method for preparing AZD4547, intermediate and preparation method of intermediate

The invention provides a method for preparing AZD-4547. The method comprises the following steps: (1) preparing a first intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate; (2) preparinga second intermediate 5-[2-(3, 5-dimethoxyphenyl) ethyl]-1H-pyrazole-3-amine by taking the first intermediate as a raw material; and (3) in an alkali-containing organic solvent, carrying out a reaction on a third intermediate 4-((3S, 5R)-3, 5-dimethylpiperazinyl-1-yl) benzoyl chloride and the second intermediate to prepare the AZD-4547. The method has the advantages of accessible raw materials, simple technique, mild reaction conditions, convenient operation, high yield and low cost and can easily implement industrial production. The invention also provides an intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate for preparing AZD-4547 and a preparation method thereof.

Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase

Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).