(E)-ethyl 3-(1H-indol-7-yl)acrylate

Base Information

• Chemical Name: (E)-ethyl 3-(1H-indol-7-yl)acrylate
• CAS No.: 288371-42-6
• Molecular Formula: C13H13NO2
• Molecular Weight: 215.25
• Mol file: 288371-42-6.mol

Synonyms:3-(1H-Indol-7-yl)-acrylic acid ethyl ester;ethyl 3-(indol-7-yl)acrylate;(E)-3-(1H-indol-7-yl)-acrylic acid ethyl ester;

Chemical Property of (E)-ethyl 3-(1H-indol-7-yl)acrylate

Chemical Property:

• Boiling Point: 396.4±17.0 °C(Predicted)
• PKA: 16.19±0.30(Predicted)
• PSA: 42.09000
• Density: 1.200±0.06 g/cm3(Predicted)
• LogP: 2.74420

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-ethyl 3-(1H-indol-7-yl)acrylate

There total 8 articles about (E)-ethyl 3-(1H-indol-7-yl)acrylate 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: 91.0%

1-(cyclohexylthio)-1H-indole + ethyl acrylate (140-88-5,9003-32-1) → 3-(1H-indol-7-yl)acrylic acid ethyl ester (288371-42-6)

Guidance literature:

1-(cyclohexylthio)-1H-indole; ethyl acrylate; With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; silver(I) triflimide; In tert-butyl alcohol; at 90 ℃; for 12h; Inert atmosphere; Sealed tube;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c01990

Reference yield: 80.0%

triethyl-phosphonoacetate + 1H-indole-7-carbaldehyde (1074-88-0) → 3-(1H-indol-7-yl)acrylic acid ethyl ester (288371-42-6)

Guidance literature:

With triethanolamine; potassium tert-butylate; In tetrahydrofuran;

Reference yield: 80.0%

(E)-ethyl 3-(1-(pyridin-2-ylsulfonyl)-1H-indol-7-yl)acrylate → 3-(1H-indol-7-yl)acrylic acid ethyl ester (288371-42-6)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran;

DOI:10.1039/c5ra02245b

upstream raw materials:

1H-indole-7-carbaldehyde

diethoxyphosphoryl-acetic acid ethyl ester

ethyl acrylate

N-(2-pyridyl)sulfonyl indoline

Downstream raw materials:

ethyl 3-(1H-indol-7-yl)propanoate

(E)-3-(1H-indol-7-yl)acrylic acid

Refernces

• 1、 Kona, Chandrababu Naidu,Nishii, Yuji,Miura, Masahiro. "Sulfur-Directed C7-Selective Alkenylation of Indoles under Rhodium Catalysis". supporting information. p. 6252 - 6256. Retrieved 2021/08/30.
• 2、 Singh, Jasbir,Zeller, Wayne,Zhou, Nian,Hategan, Georgeta,Mishra, Rama K.,Polozov, Alex,Yu, Peng,Onua, Emmanuel,Zhang, Jun,Ramírez, José L.,Sigthorsson, Gudmundur,Thorsteinnsdottir, Margret,Kiselyov, Alex S.,Zembower, David E.,Andrésson, Thorkell,Gurney, Mark E.. "Structure - activity relationship studies leading to the identification of (2E)-3-[l-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4, 5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a potent and selective prostanoid EP3 receptor antagonist, as a novel antiplatelet agent that does not prolong bleeding". experimental part. p. 18 - 36. Retrieved 2010/04/26.