220805-71-0

Basic information

• Product Name: N,N-diethyl-3,4,5-trimethoxy-2-(4-methoxy-5-oxo-1,3,6-cycloheptatrienyl)benzamide
• Synonyms: N,N-diethyl-3,4,5-trimethoxy-2-(4-methoxy-5-oxo-1,3,6-cycloheptatrienyl)benzamide
• CAS NO: 220805-71-0
• Molecular Weight: 401.459
• Mol File: 220805-71-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N,N-diethyl-3,4,5-trimethoxy-2-(4-methoxy-5-oxo-1,3,6-cycloheptatrienyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-diethyl-3,4,5-trimethoxy-2-(4-methoxy-5-oxo-1,3,6-cycloheptatrienyl)benzamide(220805-71-0)
• EPA Substance Registry System: N,N-diethyl-3,4,5-trimethoxy-2-(4-methoxy-5-oxo-1,3,6-cycloheptatrienyl)benzamide(220805-71-0)

Safety Data

• Hazardous Substances Data: 220805-71-0(Hazardous Substances Data)

Upstream product

• 118-41-2 Eudesmic acid 
• 33816-51-2 5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one 
• 5470-42-8 N,N-diethyl(3,4,5-trimethoxyphenyl)carboxamide 

Relevant articles and documents

Stereochemical variations on the colchicine motif. Part 4. A remote metalation approach toward a colchicine analog with a five-membered B-ring.

Attempts to prepare a colchicine analog with a 5-membered B-ring by remote metalation of N,N-diethyl-3,4,5-trimethoxy-2-(5'-methoxy-4'-oxo-2', 5',7'-cycloheptatrienyl)-benzamide (2) led to ring contraction of the methoxytropone ring to the p-methoxycarbonylphenyl derivative (3). Dynamic 1H NMR investigations showed that the biaryl amide 2 exists as a mixture of diastereomers due to hindered rotation around both aryl-aryl and aryl-amide bonds, with rotational barriers of ca. 63 kJ mol-1. The colchicine and allocolchicine analogs 2 and 3 do not notably affect tubulin polymerization, despite the structural similarities with active analogs. The reduced tubulin binding activity of 2 and 3 may be a result of increasing steric bulk.