108335-05-3

Basic information

• Product Name: eudistomin T
• Synonyms: eudistomin T;2-Phenyl-1-(9H-pyrido[3,4-b]indol-1-yl)ethanone;Eudistomine T
• CAS NO: 108335-05-3
• Molecular Formula: C₁₉H₁₄N₂O
• Molecular Weight: 286.32726
• Mol File: 108335-05-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 530.2°Cat760mmHg
• Flash Point: 268.1°C
• Appearance: /
• Density: 1.293g/cm³
• Vapor Pressure: 2.52E-11mmHg at 25°C
• Refractive Index: 1.736
• CAS DataBase Reference: eudistomin T(CAS DataBase Reference)
• NIST Chemistry Reference: eudistomin T(108335-05-3)
• EPA Substance Registry System: eudistomin T(108335-05-3)

Safety Data

• Hazardous Substances Data: 108335-05-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 3605, 1989 DOI: 10.1016/S0040-4039(01)80460-3

InChI:InChI=1/C19H14N2O/c22-17(12-13-6-2-1-3-7-13)19-18-15(10-11-20-19)14-8-4-5-9-16(14)21-18/h1-11,21H,12H2

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Relevant articles and documents

β-Carboline alkaloids, V: Total synthesis of the antimicrobial marine alkaloid eudistomin T

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Preparation method of 1-carbonyl-beta-carboline compound

The invention discloses a preparation method of a 1-carbonyl-beta-carboline compound. The preparation method comprises the following step: in an air or oxygen atmosphere, in the presence of an additive and under the condition of illumination, performing oxidation reaction on tetrahydrocarboline compound as shown in a formula II to obtain the 1-carbonyl-beta-carboline compound as shown in a formula I, wherein the additive is tetrabutyl quaternary ammonium salt selected from any one of tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium acetate and tetrabutylammonium fluoride; and the molar ratio of the tetrahydrocarboline compound as shown in the formula II to the additive is 1:(0.2-2). The preparation method provided by the invention is high in yield, wherein most of the yield is between 60% and 90%. When R3 is an aromatic group, the variety and the position of a substituent group on an aromatic ring do not have substantial influence on the yield of the reaction. In addition, the R3 group has wider applicability and also comprises an alkyl R3 group besides the aromatic R3 group, and in this aspect, the preparation method provided by the invention is substantially improved compared with the existing synthesis.

Iminophosphorane-mediated synthesis of 1-acyl-β-carbolines : A new access to the alkaloids eudistomin T, S and xestomanzamine A of marine origin

New syntheses of the alkaloids eudistomin T and S are described. The key step, formation of the 1-phenylacetyl β-carboline, involves a tandem aza Wittig/electrocyclic ring closure process. The first synthesis of the alkaloid xestomanzamine A is achieved by coupling of a N-protected harmane, now available via aza Wittig/electrocyclic ring closure process, with a 5-lithioimidazole derivative.