19877-89-5

Basic information

• Product Name: vincanol
• Synonyms: vincanol;(3α,14α,16α)-14,15-Dihydroeburnamenin-14-ol
• CAS NO: 19877-89-5
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.412
• EINECS: 243-388-9
• Mol File: 19877-89-5.mol

Chemical Properties

• Melting Point: 108-110 °C
• Boiling Point: 484.4 °C at 760 mmHg
• Flash Point: 246.8 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.719
• PKA: 14.30±0.40(Predicted)
• CAS DataBase Reference: vincanol(CAS DataBase Reference)
• NIST Chemistry Reference: vincanol(19877-89-5)
• EPA Substance Registry System: vincanol(19877-89-5)

Safety Data

• Hazardous Substances Data: 19877-89-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H24N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,16,18,22H,2,5,8-12H2,1H3/t16-,18+,19-/m0/s1

Upstream product

• 111687-23-1 19-oxoeburnamonine 
• 4880-88-0 vinburnine 
• 111687-22-0 (1S,12bS)-1-ethyl-1-(2-hydroxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine 
• 111687-25-3 (1S,12bR)-1-ethyl-1-(2-hydroxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine 
• 102631-76-5 3-Ethyl-3-((E)-2-nitro-vinyl)-tetrahydro-pyran-2-one 
• 111154-23-5 3-(3-Ethyl-2-methoxy-tetrahydro-furan-3-yl)-propionic acid 
• 111154-20-2 3-Ethyl-5-hydroxy-3-(3-hydroxy-propyl)-dihydro-furan-2-one 
• 199190-53-9 3-(3-Ethyl-2-oxo-tetrahydro-furan-3-yl)-propionic acid 
• 1354568-46-9 (S)-2-allyl-2-ethyl-N-benzoyl-δ-valerolactam 

Downstream Products

• 1617-90-9 vincamin 
• 2580-88-3 (-)-eburnamonine 
• 4880-88-0 vinburnine 
• 65026-49-5 (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2,4,6,8⁽¹⁸⁾-tetraene 

Related news

Vincamine and vincanol (cas 19877-89-5) are potent blockers of voltage-gated Na + channels09/25/2019

The effects of three vinca derivatives on [ 3 H]batrachotoxin binding in rat cortical synaptosomes, on the inhibition of whole-cell Na + currents evoked in voltage-clamped cortical neurones of the rat, on the protection against veratridine-induced cell death in cortical cultures ...detailed

Relevant articles and documents

Intermediate, preparation method and application of intermediate in synthesis of vincamine

The invention relates to the technical field of chemical drug synthesis, and discloses an intermediate, a preparation method and application of the intermediate in synthesis of vincamine. A modular synthesis strategy is adopted, and a compound 1 with a D ring structure and a C20 quaternary carbon center and a tryptophol derivative 7 (namely the compound 7) with an indole ring are adopted as synthesis blocks for synthesis. The synthesis method is efficient; each step of the synthesis route is simple in reaction; the used reagent and solvent are cheap and easy to obtain; the operation is simple and convenient; the yield is high; and large-scale production is easy.

Intermediate and preparation method and application thereof in synthesis of vinorchine

The invention relates to the technical field of chemical drug synthesis, and discloses an application of an intermediate or a preparation method thereof in synthesis of vinorchin, adopts a modular synthetic strategy, adopts the compound D with 1 ring structures and C20 quaternary carbon centers, 5 (i.e. the compound 5) as a synthesis building block. The operation is simple and reaction conditions are easy for large-scale amplification effect.

The synthesis of melohenine B and a related natural product

A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

Synthesis of eburnamine, isoeburnamine, and eburnamonine via a spirocyclic intermediate

Racemic eburnamonine (1) was synthesized via 6, an intermediate possessing local symmetry. Cleavage of the cyclopentene subunit led to pentacyclic aldehydes 8a/8b which on subsequent borohydride and Wolff-Kishner reductions gave 12. The final steps included a RuCl3-catalyzed periodate oxidation and pyridinium chlorochromate (PCC) oxidation. The penultimate intermediates were racemic eburnamine (2) and racemic isoeburnamine (3).

Synthesis of Vinca Alkaloids and Related Compounds. Part LXVIII. Two Diastereoisomeric Aspidosperma-Eburnea Type Bis-indoles: Their Synthesis and Structure Revisited

With the aim of clarifying their previously incorrectly depicted structure, the indole-indoline type compounds 11 and 12 were synthesized via different routes.The results presented here are a detailed account of the synthetic aspects of this work, and also redress some points of an earlier paper on this topic.

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines

STRUCTURE OF GONIOMITINE, A NEW TYPE OF INDOLE ALKALOID

The structure 1 proposed for goniomitine, an indole alkaloid isolated from the root bark of Gonioma malagasy (Apocynaceae), was inferred from an analysis of its MS, 1H and 13C NMR spectral data.A biogenetic scheme is proposed to account for the formation of 1 from vincadifformine 9.

METHODS FOR INDOLE ALKALOID SYNTHESIS: REACTIONS OF N-ARYLSULFONYLENAMINES WITH ELECTROPHILES. AN EXPEDITIOUS SYNTHESIS OF (+/-)-EBURNAMONINE.

Treatment of 4 with MCPBA gave 9.The pentacyclic amide 3 on exposure to cyanogen chloride gave the cis-chloro-hydrin 20, and the geminal dichloride 21.When 21 was treated with HCl/MeOH it rapidly rearranged to eburnamonine lactam 22.

Total Synthesis of (-)-Kopsinilam, (-)-Kopsinine, and the Bis-indole Alkaloids (-)-Norpleiomutine and (-)-Pleiomutine

The racemic tetracyclic amine (5) was resolved and converted into (-)-kopsinine (16); subsequent coupling to (-)-eburnamine (2) gave (-)-norpleiomutine (4).