1104967-34-1

Basic information

• Product Name: 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one
• Synonyms: 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one
• CAS NO: 1104967-34-1
• Molecular Weight: 383.444
• Mol File: 1104967-34-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one(1104967-34-1)
• EPA Substance Registry System: 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one(1104967-34-1)

Safety Data

• Hazardous Substances Data: 1104967-34-1(Hazardous Substances Data)

Upstream product

• 64728-23-0 2-(3,4-dimethoxyphenyl)-1-iodoethane 
• 73942-87-7 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 73954-34-4 N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide 

Relevant articles and documents

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.

A new synthetic approach towards isoquinobenzazepinone and isoindolinobenzazepinone using acid-mediated cyclisation and Heck reaction

Six-membered ring cyclisation of N-ethylbenzazepinone, prepared from the condensation of benzazepinone with phenethyl iodide under basic conditions, smoothly provided the corresponding product, isoquino[1,2-b][3]benzazepinone, under acid-mediated conditions. On the other hand, the attempted direct five-membered ring cyclisation using the acid-mediated conditions failed to give the 7,5 fused ring isoindolinobenzazepinone from N-benzylbenzazepinone, but the 7,6 fused ring product was instead obtained. However, five-membered ring cyclisation of N-benzylbenzazepinone could be effected efficiently by employing the Heck reaction followed by catalytic hydrogenation to furnish the desired isoindolinobenzazepinone.