181769-06-2

Basic information

• Product Name: 2-Chloro-N-[2-(4-methoxy-cyclohexa-1,4-dienyl)-ethyl]-acetamide
• CAS NO: 181769-06-2
• Molecular Weight: 229.707
• Mol File: 181769-06-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Chloro-N-[2-(4-methoxy-cyclohexa-1,4-dienyl)-ethyl]-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-[2-(4-methoxy-cyclohexa-1,4-dienyl)-ethyl]-acetamide(181769-06-2)
• EPA Substance Registry System: 2-Chloro-N-[2-(4-methoxy-cyclohexa-1,4-dienyl)-ethyl]-acetamide(181769-06-2)

Safety Data

• Hazardous Substances Data: 181769-06-2(Hazardous Substances Data)

Upstream product

• 67175-79-5 2-(4-methoxycyclohexa-1,4-dienyl)ethylamine 
• 79-04-9 chloroacetyl chloride 

Relevant articles and documents

Total synthesis of (±)-deethylibophyllidine: Studies of a Fischer indolization route and a successful approach via a Pummerer rearrangement/thionium ion-mediated indole cyclization

The total synthesis of (±)-deethylibophyllidine is described, proceeding in eight steps from 4-(methoxyphenyl)ethylamine in 5% overall yield (Scheme 6). In terms of sequential annulation, the strategy involves the following operations: E → DE → ABDE → ABCDE (Scheme 1). The key steps in the synthesis are the stereoselective formation of octahydroindol-6-ones by acid treatment of dihydroanisole derivatives, the regioselective Fischer indolization to obtain octahydropyrrolo[3,2-c]carbazoles, and the tandem process consisting of Pummerer rearrangement upon a β-amino sulfoxide and thionium ion cyclization upon a β-indole position of a 2,3-disubstituted indole to generate the quaternary spiro center. Attempts to effect the construction of the pentacyclic framework by means of Fischer indolization of the octahydropyrrolo[3,2,1-hi]indol-6-one resulted in failure (Scheme 2).