336883-76-2

Basic information

• Product Name: 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione
• Synonyms: 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione
• CAS NO: 336883-76-2
• Molecular Weight: 531.611
• Mol File: 336883-76-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione(336883-76-2)
• EPA Substance Registry System: 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione(336883-76-2)

Safety Data

• Hazardous Substances Data: 336883-76-2(Hazardous Substances Data)

Upstream product

• 1026294-20-1 3-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-4-(indol-3-yl)-3-pyrroline-2,5-dione 
• 336883-73-9 methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate 
• 336883-71-7 tert-butyl 2-{3-indolyl-1-[(phenylmethoxy)methyl]propoxy}acetate 
• 336883-78-4 methanesulfonic acid 2-(1-benzyloxymethyl-3-indol-1-yl-propoxy)-ethyl ester 
• 336883-72-8 2-{3-indolyl-1-[(phenylmethoxy)methyl]propoxy}ethan-1-ol 
• 336883-70-6 4-indolyl-1-(phenylmethoxy)butan-2-ol 
• 336883-68-2 1-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethyl]-1H-indole 
• 336883-69-3 4-indolylbutane-1,2-diol 
• 120-72-9 indole 
• 336883-75-1 3-{1-[3-(2-bromoethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-4-(indol-3-yl)-3-pyrroline-2,5-dione 
• 879-37-8 3-indolylacetamide 
• 336883-79-5 methyl 2-(1-{3-[2-(methylsulfonyloxy)ethoxy]-4-(phenylmethoxy)butyl}indol-3-yl)-2-oxoacetate 

Downstream Products

• 336883-78-4 methanesulfonic acid 2-(1-benzyloxymethyl-3-indol-1-yl-propoxy)-ethyl ester 

Relevant articles and documents

Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides

Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl imide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.