60031-91-6

Basic information

• Product Name: methyl (2S)-2-[(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate (non-preferred name)
• Synonyms: 17,18-Secoyohimban-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (16S,19E)-; Corynan-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (16R,19E)-
• CAS NO: 60031-91-6
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.4427
• Mol File: 60031-91-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 558.9°C at 760 mmHg
• Flash Point: 291.8°C
• Density: 1.26g/cm³
• Vapor Pressure: 2.49E-13mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: methyl (2S)-2-[(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S)-2-[(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate (non-preferred name)(60031-91-6)
• EPA Substance Registry System: methyl (2S)-2-[(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate (non-preferred name)(60031-91-6)

Safety Data

• Hazardous Substances Data: 60031-91-6(Hazardous Substances Data)

Upstream product

• 117626-39-8 (+/-)-Ethyl 4-oxo-2-<(E)-1-(trimethylsilyl)-1-propenyl>-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 117626-39-8 (+/-)-Ethyl 4-oxo-2-<(Z)-1-(trimethylsilyl)-1-propenyl>-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 117626-42-3 (+/-)-Methyl 2,3,4,9-Tetrahydro-β-<(E)-1-(trimethylsilyl)-1-propenyl>-1H-pyrido<3,4-b>indole-1-butanoate 
• 117626-42-3 (+/-)-Methyl 2,3,4,9-Tetrahydro-β-<(Z)-1-(trimethylsilyl)-1-propenyl>-1H-pyrido<3,4-b>indole-1-butanoate 
• 117626-41-2 (+/-)-4-Oxo-2-<(E)-1-(trimethylsilyl)-1-propenyl>-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine 
• 117626-41-2 (+/-)-4-Oxo-2-<(Z)-1-(trimethylsilyl)-1-propenyl>-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine 
• 117626-38-7 (+/-)-Ethyl 4-oxo-1,4,6,7,12,12b-hexahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 117626-36-5 3-<2'-((5'-Oxo-5'-ethoxy-4'-(ethoxycarbonyl)penta-1',3'-dienyl)amino)ethyl>-1H-indole 
• 117626-37-6 (+/-)-Ethyl 2-(ethoxycarbonyl)-4-(2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-yl)butenoate 
• 3040-24-2 diethyl [3-ethoxyprop-2-enylidene]malonate 
• 61-54-1 tryptamine 
• 23107-03-1 (+/-)-(19Z)-Methyl Geissoschizoate 
• 67685-79-4 2-[(2S,12bS)-3-((E)-2-Methoxycarbonyl-vinyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-2-yl]-malonic acid dimethyl ester 
• 118577-66-5 (E)-3-[(2R,12bS)-2-(Ethoxycarbonyl-methylsulfanyl-methyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-3-yl]-acrylic acid ethyl ester 

Relevant articles and documents

Total Syntheses of Naucleamides A-C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine

A divergent approach for the enantioselective total synthesis of eight monoterpenoid indole alkaloids was developed. The approach allows the first total syntheses of naucleamides A-C and E in only 6-8 steps and also enables the efficient synthesis of geissoschizine, geissoschizol, (E)-isositsirikine, and 16-epi-(E)-isositsirikine in 10-11 steps from commercially available crotonic aldehyde. The synthesis features a one-pot organocatalyzed asymmetric Michael addition/Pictet-Spengler reaction. Notably, biomimetic synthesis of naucleamide E was achieved by oxidative cyclization of naucleamide A.

ALKALOIDS FROM RHAZYA STRICTA

Chemical investigations of roots and leaves of Rhazya stricta have resulted in the isolation of the new indole alkaloids, 16R-19,20-E-isositsirikine acetate, leepacine and dihydroeburnamenine, along with six known alkaloids.Among these, (-)-16R,21R-O-methyleburnamine, 2-ethyl-3-indole, (20S)-19,20-dihydrocondylocarpine and N-acetylaspidospermidine have been isolated for the first time from R. stricta.Spectral studies on (+)-21S-eburnamenine and the glycoalkaloid strictosamide have also been undertaken. --- Key Word Index: Rhazya stricta; Apocynaceae; indole alkaloide; glycoalkaloids; 13C NMR.

Total syntheses of (+)-geissoschizine, (±)-geissoschizine, and (±)-(Z)-isositsirikine. Stereocontrolled synthesis of exocyclic double bonds by stereospecific iminium ion-vinylsilane cyclizations

(+)-Geissoschizine (1) was prepared in an efficient and stereocontrolled fashion in 11 steps and 7.5% overall yield from (S)-tryptophanamide (20). Key steps are the stereoselective 1,4-addition of cuprate 13a to tetracyclic intermediate 8, which establish