3247-10-7

Basic information

• Product Name: Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5α,12β,19α)-
• Synonyms: Vincadifformine; 6,7-Dihydrotabersonine; Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5alpha,12beta,19alpha)-; methyl (5alpha,12beta,19alpha)-2,3-didehydroaspidospermidine-3-carboxylate; 15-Bromovincadifformine
• CAS NO: 3247-10-7
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.4433
• EINECS: 221-823-3
• Mol File: 3247-10-7.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 474.5°C at 760 mmHg
• Flash Point: 240.8°C
• Density: 1.24g/cm³
• Vapor Pressure: 3.6E-09mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5α,12β,19α)-(CAS DataBase Reference)
• NIST Chemistry Reference: Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5α,12β,19α)-(3247-10-7)
• EPA Substance Registry System: Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5α,12β,19α)-(3247-10-7)

Safety Data

• Hazardous Substances Data: 3247-10-7(Hazardous Substances Data)

Upstream product

• 55475-53-1 20-iodo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester 
• 17172-16-6 14,15-dihydrovindolinine 
• 91208-71-8 C₂₁H₂₆N₂O₂ 
• 80658-39-5 C₂₁H₂₅ClN₂O₂ 
• 55856-70-7 19-Iodo-tabersonine 
• 4429-63-4 tabersonine 
• 77255-84-6 16-nitro-1,2-dehydro-2,16-dihydro vincadifformine 
• 55528-28-4 8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester 
• 55528-27-3 3-oxovincadifformine 
• 41787-54-6 16-epi-19-S-vindolinine 
• 74129-83-2 (-)-(hydroxymethyl)norvincadifformine 
• 32789-67-6 16-chloro-1-dehydro-vincadifformine 
• 32975-46-5 (-)-1,2,14,15-tetradehydroaspidospermidine 
• 124293-81-8 1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde 

Downstream Products

• 6835-99-0 14-epivincamine 
• 1617-90-9 vincamin 
• 56245-51-3 (-)-dehydro-1,2 aspidospermidine 
• 38199-30-3 Δ¹⁴-vincamenine 
• 4880-92-6 apovincamine 
• 55700-36-2 2,16-dihydrovincadifformine 
• 143207-13-0 (3aS,5S,5aS,10bS,12bS)-6-Acetyl-3a-ethyl-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester 
• 18374-17-9 (±)-vincadifformine 
• 19751-76-9 (+)-1,2-didehydroaspidospermidine 
• 260362-08-1 14β-benzyl-1,2-didehydroaspidospermidine 
• 260362-03-6 14β-benzyl-(N_a-tert-butoxy-carbonyl)vicadifformine 
• 260362-00-3 14β-benzyl-3-oxo-(N_a-tert-butoxycarbonyl)vincadifformine 
• 260362-12-7 14β-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 
• 260362-01-4 14α-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 

Relevant articles and documents

Rearrangement and photolysis of aziridines in the aspidosperma series

Rearrangement of aziridine 1 by MgBr2 gave 2-H-dihydro-17- dehydrovincadifformine 6. Photolysis transformed aziridines 1 and 11 into the new compounds 1,2-seco-1,21-cyclovincadifformine 10 and 1,2-seco-1,21- cyclotabersonine 12.

Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea-Phosphonium Salt Catalyzed Mannich-Type Reaction

An asymmetric total synthesis of vincadifformine is described. The limited tactics with chiral cation-directed catalysis in total synthesis inspired the development of our strategy for accessing this alkaloid in enantionrich form. The route features a thiourea–phosphonium salt catalyzed Mannich-type reaction, a phosphine-promoted aza-Morita–Baylis–Hillman reaction and a trifluoroacetic acid promoted deprotection/amidation cascade process.

Vincamine preparation method

The invention relates to a vincamine preparation method in the field of compound preparation. The vincamine preparation method includes the steps of (1), tabersonine preparation, (2), vincadifformine preparation, (3), monoperoxy maleic acid preparation and (4), vincamine preparation. The vincamine preparation method has the advantages of easy availability to raw materials, simplicity and convenience in reaction process operation, high safety, low cost, high product yield, high quality and suitability for industrial production.