59444-69-8

Basic information

• Product Name: eudistomin N
• Synonyms: eudistomin N;6-Bromo-9H-pyrido[3,4-b]indole;6-Bromonorharman;Eudistomine N
• CAS NO: 59444-69-8
• Molecular Formula: C₁₁H₇BrN₂
• Molecular Weight: 247.09068
• Mol File: 59444-69-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 443.6°C at 760 mmHg
• Flash Point: 222.1°C
• Appearance: /
• Density: 1.699g/cm³
• Vapor Pressure: 1.2E-07mmHg at 25°C
• Refractive Index: 1.799
• CAS DataBase Reference: eudistomin N(CAS DataBase Reference)
• NIST Chemistry Reference: eudistomin N(59444-69-8)
• EPA Substance Registry System: eudistomin N(59444-69-8)

Safety Data

• Hazardous Substances Data: 59444-69-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7BrN2/c12-7-1-2-10-9(5-7)8-3-4-13-6-11(8)14-10/h1-6,14H

Upstream product

• 244-63-3 betacarboline 
• 6250-88-0 4,9-Dihydropyrano<3,4-b>indol-1(3H)-on 
• 110977-90-7 6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on 
• 162272-89-1 2-(4-Chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol 
• 162272-90-4 6-Brom-2-(4-chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol 
• 162272-83-5 2-(4-Chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-on 
• 162272-84-6 6-Brom-2-(4-chlorbenzyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-on 
• 42438-90-4 3-carboxy-1,2,3,4-tetrahydro-2-carboline 
• 73-22-3 L-Tryptophan 

Downstream Products

• 1221437-41-7 6-bromo-2-(3-phenyl-propyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-37-1 2-benzyl-6-bromo-9H-beta-carbolin-2-ium bromide 
• 1221437-39-3 6-bromo-2-(3-fluoro-benzyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-38-2 6-bromo-2-(4-fluoro-benzyl)-9H-beta-carbolin-2-ium bromide 
• 1221437-40-6 6-bromo-2-(4-nitro-benzyl)-9H-beta-carbolin-2-ium bromide 

Relevant articles and documents

A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air

A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.

Iodine-catalyzed one-pot decarboxylative aromatization of tetrahydro-β-carbolines

A synthetic strategy was developed for the preparation of β-carbolines by one-pot decarboxylation and aromatization of tetrahydro-β-carboline-3-carboxylic acids by employing 10?mol% of iodine in presence of oxidant aqueous H2O2. The method was also successfully extended for the aromatization of tetrahydro-β-carboline-3-methyl esters. The utility of the method was demonstrated in the synthesis of β-carboline alkaloids norharmane, harmane and eudistomin N.

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.