6711-69-9

Basic information

• Product Name: tubotaiwine
• Synonyms: tubotaiwine;2,16-Didehydrocondyfolan-16-carboxylic acid methyl ester;Methyl (14beta)-2,16-didehydrocondyfolan-16-carboxylate;NSC 306222;Tubotaiwin;20(S)-tubotaiwine
• CAS NO: 6711-69-9
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.42
• Mol File: 6711-69-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 467.687°C at 760 mmHg
• Flash Point: 236.649°C
• Appearance: /
• Density: 1.267g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: tubotaiwine(CAS DataBase Reference)
• NIST Chemistry Reference: tubotaiwine(6711-69-9)
• EPA Substance Registry System: tubotaiwine(6711-69-9)

Safety Data

• Hazardous Substances Data: 6711-69-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Alstonia spatulata.

InChI:InChI=1/C20H24N2O2/c1-3-12-13-8-10-22-11-9-20(18(12)22)14-6-4-5-7-15(14)21-17(20)16(13)19(23)24-2/h4-7,12-13,18,21H,3,8-11H2,1-2H3/t12-,13-,18+,20+/m0/s1

Upstream product

• 4939-81-5 (+)-condylocarpine 
• 134734-63-7 (3aRS,4SR,5SR,11bSR)-Methyl 4-ethyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-1H-pyrrolo<2,3-d>carbazole-7-carboxylate 
• 130291-34-8 C₁₆H₂₀N₂ 
• 128350-30-1 (1RS,5RS,12SR)-2-Benzyl-12-ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 
• 130291-31-5 (1RS,5RS,12SR)-2-<2,2-Bis(methylthio)ethyl>-12-ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 
• 130291-35-9 (1RS,5RS,12SR)-2-(2,2-Diethoxyethyl)-12-ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 
• 128350-42-5 (1RS,5SR,9RS)-2-Benzyl-9-ethyl-2-azabicyclo<3.3.1>nonan-7-one 
• 113386-10-0 cis-4-Acetonyl-1-benzyl-3-ethylpiperidine 
• 113386-10-0 trans-4-acetonyl-1-benzyl-3-ethylpiperidine 
• 128350-37-8 t-4-Acetonyl-1-benzyl-c-3-ethyl-r-2-piperidinecarbonitrile 
• 85704-16-1 1-(1-benzyl-4-piperidyl)-2-propanone 
• 100-63-0 phenylhydrazine 
• 130291-32-6 C₁₉H₂₄N₂S 
• 134734-62-6 C₂₁H₂₆N₂O₂S 

Relevant articles and documents

Total synthesis of (+)-condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine

The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates.

Total Syntheses of Tubotaiwine and 19,20-Dihydro-20-epi-akuammicine

Starting from the indoloazepine 9, the title products 2 and 7 were synthesized in seven steps in 27 and 22percent overall yield, respectively.