76787-76-3

Basic information

• Product Name: 5(1H)-Indolizinone, 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydro-
• CAS NO: 76787-76-3
• Molecular Formula: C24H27NO5
• Molecular Weight: 409.482
• Mol File: 76787-76-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5(1H)-Indolizinone, 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(1H)-Indolizinone, 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydro-(76787-76-3)
• EPA Substance Registry System: 5(1H)-Indolizinone, 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydro-(76787-76-3)

Safety Data

• Hazardous Substances Data: 76787-76-3(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 76787-81-0 3-oxo-2-veratroyl-butyric acid ethyl ester 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 86980-84-9 2-(3,4-Dimethoxyphenyl)-2,3,3a,4,5,6-hexahydropyrrolo<1,2-b>isoxazole 
• 90171-76-9 1-<(3,4-Dimethoxyphenyl)acetyl>-2-<2-(3,4-dimethoxyphenyl)-2-hydroxyethyl>pyrrolidine 
• 6380-23-0 3,4-dimethoxystyrene 
• 74053-93-3 methyl 3-(3,4-dimethoxyphenyl)-3-oxopropionate 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 60890-27-9 1-(3,4-dimethoxyphenyl)-2-(pyrrolidin-2-yl)ethan-1-one 

Downstream Products

• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 

Relevant articles and documents

Synthesis, in vitro and in vivo cytotoxicity of 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones

A 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-one library was constructed and tested against the colon cancer cell line HCT-116 as an initial screen for cytotoxic properties. Of this library, the parent compound, in which the southern aromatic ring remains unsubstituted, and the northern aromatic ring carries a 4-methoxy group, exhibited the most potent cytotoxicity with an IC50 value of 0.39 μM and displayed promising activity in vivo in the NCI's mouse hollow fiber assay.

General Synthesis of Phenanthroindolizidine, Phenanthroquinolizidine, and Related Alkaloids: Preparation of (+/-)-Tylophorine, (+/-)-Cryptopleurine, (+/-)-Septicine, and (+/-)-Julandine

A general synthetic route to the pentacyclic phenanthro class and related indolizidine and quinolizidine alkaloids via β-amino ketone intermediates is reported.The synthesis of tylophorine, cryptopleurine, septicine, and julandine, in racemic forms, has been described.Synthetic steps in the preparation of these alkaloids involve 1,3-dipolar cycloadditions of the cyclic nitrones as a common feature followed by crucial ring closure by aldol reactions and photolyses.

A New Synthesis of Septicine, a Secophenanthroindolizine Alkaloid

Septicine , an alkaloid isolated from Ficus septica and Tylophora asthmatica, has been synthesized using 2-(3',4'-dimethoxyphenacyl)pyrrolidine (6) and 3,4-dimethoxy-phenylacetyl chloride (11) as the essential intermediates.Condensation of 6 and 11 affords 2-(3',4'-dimethoxyphenacyl)-N-(3'',4''-dimethoxyphenylacetyl)pyrrolidine (12) which on treatment with potassium-t-butoxide furnishes 6,7-di-(3',4'-dimethoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine (13).LAH reduction of 13 affords septicine (1), identical (co-TLC, IR, PMR, m.m.p.) with a natural sample.