180922-71-8

Basic information

• Product Name: 1-BOC-2-CHLORO-3-FORMYL-INDOLE
• Synonyms: 1-BOC-2-CHLORO-3-FORMYL-INDOLE
• CAS NO: 180922-71-8
• Molecular Formula: C₁₄H₁₄ClNO₃
• Molecular Weight: 279.72
• Mol File: 180922-71-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(180922-71-8)
• EPA Substance Registry System: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(180922-71-8)

Safety Data

• Hazardous Substances Data: 180922-71-8(Hazardous Substances Data)

Usage

Type of compound

Chemical compound

Derivative of

Indole (bicyclic heterocyclic organic compound)

Formyl group

Attached to the 3rd position of the indole ring

Chlorine atom

Attached to the 2nd position of the indole ring

BOC protecting group

Attached to the 1st position (tert-butoxycarbonyl)

Reactivity

Versatile, can participate in various chemical reactions

Applications

a. Intermediate in the synthesis of pharmaceuticals
b. Intermediate in the synthesis of other organic compounds

Usage

Commonly used in the field of medicinal chemistry and drug development

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 

Downstream Products

• 26612-48-6 5,12-dihydrocycloocta[1,2b;5,6b']diindole-6,13-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters

The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.

Method for simply and efficiently synthesizing caulerpin

The invention belongs to the field of organic chemical synthesis and discloses a method for simply and efficiently synthesizing caulerpin. The method comprises the following steps: by taking 2-indolone as a raw material, firstly, performing halogenated acylation on the 2-indolone, protecting amino on indole, performing nucleophilic substitution at a site 2 of the amino, connecting malonic acid dimethyl, further performing decarboxylation and protection group removal so as to obtain 3-formyl-2-indole methyl acetate, and finally performing cyclization between two molecules, so as to obtain caulerpin. Compared with a disclosed method for synthesizing caulerpin, the method disclosed by the invention is simple in synthesis process, low in raw material cost, gentle in reaction condition, high inproduct purity, high in yield and easy in industrialization, and has a very high medical value and a wide market prospect.

The tertiary amino effect: An efficient method for the synthesis of α-Carbolines

Functionalized annelated α-Carbolines have been synthesized from oxindole following a tertiary amino effect reaction strategy. Georg Thieme Verlag Stuttgart New York.