13671-74-4

Basic information

• Product Name: 1-benzyl-1,5,6,7-tetrahydro-4H-indol-4-one
• CAS NO: 13671-74-4
• Molecular Formula: C₁₅H₁₅NO
• Molecular Weight: 225.2857
• Mol File: 13671-74-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 382°C at 760 mmHg
• Flash Point: 184.8°C
• Density: 1.14g/cm³
• Vapor Pressure: 4.86E-06mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 1-benzyl-1,5,6,7-tetrahydro-4H-indol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-1,5,6,7-tetrahydro-4H-indol-4-one(13671-74-4)
• EPA Substance Registry System: 1-benzyl-1,5,6,7-tetrahydro-4H-indol-4-one(13671-74-4)

Safety Data

• Hazardous Substances Data: 13671-74-4(Hazardous Substances Data)

Usage

Chemical class

Alkaloid

Source

Derived from the Uncaria plant

Biological activities

Antimalarial
Anti-inflammatory
Neuroprotective

Potential applications

Treatment of neurodegenerative diseases (e.g., Parkinson's disease)
Dopaminergic neuroprotective agent

Weight loss and anti-obesity potential

Inhibits the enzyme alpha-amylase, which is involved in the digestion of carbohydrates

Pharmacological and therapeutic applications

Interest across various health conditions due to its diverse range of biological activities

Upstream product

• 76327-74-7 2-ethoxy-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 100-46-9 benzylamine 
• 504-02-9 1,3-cylohexanedione 
• 56671-28-4 4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid 
• 82584-78-9 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid methyl ester 
• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 16806-93-2 4-oxo-4,5,6,7-tetrahydrobenzofuran 
• 24461-61-8 phenylglycine methyl ester 
• 76327-75-8 2-(2',2'-diethoxyethyl)-1,3-cyclohexanedione 
• 35768-38-8 3-hydroxy-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 53386-64-4 methyl 2-(benzylamino)acetate 
• 187085-47-8 N-benzyl-N-<7-(trimethylsilyl)-5-oxohept-6-yn-1-oyl>glycine methyl ester 
• 187085-44-5 7-(trimethylsilyl)-5-oxohept-6-ynoic acid 

Downstream Products

• 95969-10-1 1-Benzyl-5-chloro-1,5,6,7-tetrahydro-indol-4-one 
• 107170-59-2 [1-Benzyl-1,5,6,7-tetrahydro-indol-(4Z)-ylidene]-acetonitrile 
• 107170-58-1 [1-Benzyl-1,5,6,7-tetrahydro-indol-(4E)-ylidene]-acetonitrile 
• 107170-64-9 [1-Benzyl-1,5,6,7-tetrahydro-indol-(4E)-ylidene]-acetic acid ethyl ester 

Relevant articles and documents

A Novel and Chemoselective Process of N -Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.

Microwave-assisted synthesis of tetrahydroindoles

An efficient synthesis of tetrahydroindoles with different substituents in position 1 is described. Microwave-assisted aminolysis of 4-oxo-4,5,6,7-tetrahydrobenzofuran with different primary amines gives the corresponding tetrahydroindoles in few minutes.

A simple and general synthesis of 4-oxo-4,5,6,7-tetrahydroindoles via a novel intramolecular 1,3-dipolar cycloaddition approach

A general synthesis of 4-keto-4,5,6,7-tetrahydroindoles 6-12 has been achieved in two steps using a new intramolecular 1,3-dipolar cycloaddition approach in moderate yields (45-60%). The potential of this methodology is demonstrated by the synthesis of a mitomycin skeleton (15) and a topoisomerase-1 inhibitor skeleton (17).