66859-30-1

Basic information

• Product Name: AZEPINO[4,5-B]INDOLE-5-CARBOXYLIC ACID,1,2,3,4,5,6-HEXAHYDRO-3-(PHENYLMETHYL)-,METHYL ESTER
• Synonyms: AZEPINO[4,5-B]INDOLE-5-CARBOXYLIC ACID,1,2,3,4,5,6-HEXAHYDRO-3-(PHENYLMETHYL)-,METHYL ESTER;1,2,3,4,5,6-Hexahydro-3-(phenylmethyl)azepino[4,5-b]indole-5-carboxylic acid methyl ester
• CAS NO: 66859-30-1
• Molecular Formula: C₂₁H₂₂N₂O₂
• Molecular Weight: 334.417
• Mol File: 66859-30-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: AZEPINO[4,5-B]INDOLE-5-CARBOXYLIC ACID,1,2,3,4,5,6-HEXAHYDRO-3-(PHENYLMETHYL)-,METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZEPINO[4,5-B]INDOLE-5-CARBOXYLIC ACID,1,2,3,4,5,6-HEXAHYDRO-3-(PHENYLMETHYL)-,METHYL ESTER(66859-30-1)
• EPA Substance Registry System: AZEPINO[4,5-B]INDOLE-5-CARBOXYLIC ACID,1,2,3,4,5,6-HEXAHYDRO-3-(PHENYLMETHYL)-,METHYL ESTER(66859-30-1)

Safety Data

• Hazardous Substances Data: 66859-30-1(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 66859-22-1 methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate 
• 146681-75-6 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester 
• 69069-58-5 dimethyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5,5-dicarboxylate 
• 18871-63-1 3,3-ethylenedioxybutanal 
• 53590-32-2 3-(2-aminoethyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride 
• 100-44-7 benzyl chloride 
• 146681-78-9 N_b,N_b-dibenzyl-2-(hydroxymethyl)tryptamine 
• 146681-80-3 N_b,N_b-dibenzyl-2-(cyanomethyl)tryptamine 
• 146681-77-8 N_b,N_b-dibenzyl-2-(ethoxycarbonyl)tryptamine 
• 146681-76-7 Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate 
• 146681-79-0 N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine 
• 146681-81-4 2-[3-(2-Dibenzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester 
• 343-94-2 tryptamine hydochloride 

Downstream Products

• 77080-62-7 N^b-benzyl-D-nordeethylvincadifformine 
• 77080-67-2 (+/-)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15-dinoraspidospermidine 
• 77080-80-9 2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α) 
• 77122-17-9 2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20β,21α) 
• 131829-79-3 (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 131829-82-8 (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 121464-75-3 methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 634597-10-7 methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-(S)-(tert-butyldimethylsilyloxy)-2-(tosyloxymethyl)propyl]-1H-pyrrolo(2,3-d)carbazole-6-carboxylate 
• 634597-08-3 methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-(S)-(trimethylsilyloxy)-2-(tosyloxymethyl)propyl]-1H-pyrrolo(2,3-d)carbazole-6-carboxylate 

Relevant articles and documents

Synthesis of vinca alkaloids and related compounds. Part 101: A new convergent synthetic pathway to build up the aspidospermane skeleton. Simple synthesis of 3-oxovincadifformine and 3-oxominovincine. Attempts to produce 15β-hydroxyvincadifformine

A molecule with an indole skeleton, containing a latent acrylic ester function - acting as a diene - was produced from Nb-trityl-2-(hydroxy-methyl)-tryptamine and reacted with esters containing an aldehyde or aldehyde-equivalent structural unit, yielding 3-oxo-16,17-dihydro-Δ20-secodin-17-ol type intermediates from which dehydration, followed by [4+2]cycloaddition, furnished 3-oxovincadifformine and 3-oxominovincine. We also wished to apply the method to produce 15β-hydroxyvincadifformine, however, the appearance of a dimeric product with indole skeleton was observed instead of the expected cycloaddition.

Synthesis of Vinca Alkaloids and Related Compounds. 63. A New Synthetic Pathway for Preparing Alkaloids and Related Compounds with the Aspidosperma Skeleton. Total Syntheses of (+/-)-Vincadifformine, (+/-)-Tabersonine, and (+/-)-3-Oxotabersonine

Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of (2-ethoxycarbonyl)tryptamine (2).The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43).The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tricyclic benzoate esters 37 and 38.The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

Studies in Biomimetic Alkaloid Syntheses. 5. Total Syntheses of ψ-Vincadifformine, 20-Epi-ψ-vincadifformine, Pandoline, 20-Epipandoline and the C-16 Epimeric (Carbomethoxy)velbanamines.

The title racemic pentacyclic alkaloids (5b-e) were synthesized by respective reactions of the indoloazepines 8b,c with the halopentanals 10a,b or the epoxypentanal 23.Reductive opening of pandoline (5d) gave the racemic seco compounds 28a,b, and reductiv