13754-86-4

Basic information

• Product Name: 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• Synonyms: 4-Oxo-1,5,6,7-tetrahydroindole;1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE;1,5,6,7-TETRAHYDRO-4H-INDOLE-4-ONE;1,5,6,7-TETRAHYDRO-INDOL-4-ONE;4-OXO-4,5,6,7-TETRAHYDROINDOLE;Tetrahydroindolone;4-0xo-4,5,6,7-tetrahydroindole;1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE 97+%
• CAS NO: 13754-86-4
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 13754-86-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 188-190 °C(lit.)
• Boiling Point: 311℃
• Flash Point: 150℃
• Appearance: /
• Density: 1.216
• Vapor Pressure: 0.000593mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 15.91±0.20(Predicted)
• CAS DataBase Reference: 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)
• EPA Substance Registry System: 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 13754-86-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13754-86-4 differently. You can refer to the following data:
1. ? ;Reactant in synthesis of psammopemmin A as antitumor agent1? ;Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions2? ;Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase3? ;Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles4? ;Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids foll
2. 1,5,6,7-Tetrahydro-4H-indol-4-one, is a versatile building block used for the synthesis of more complex pharmaceutical compounds. It can be used for the preparation of Psammopemmin A.

General Description

Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl--4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate) yields α-iodo derivative as the main product.

InChI:InChI=1/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2

Upstream product

• 56671-28-4 4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid 
• 504-02-9 1,3-cylohexanedione 
• 141-43-5 ethanolamine 
• 76327-74-7 2-ethoxy-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 76327-75-8 2-(2',2'-diethoxyethyl)-1,3-cyclohexanedione 
• 128428-59-1 3-hydroxy-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-3-carboxylic acid ethyl ester 
• 101363-20-6 Acetic acid (1S,2R,3S,4R)-2,3,4,5-tetraacetoxy-1-{(R)-2-[(Z)-hydroxyimino]-4-oxo-2,3,4,5,6,7-hexahydro-benzofuran-3-yl}-pentyl ester 
• 101363-20-6 (E)-(3R)-3,5,6,7-tetrahydro-2-hydroxyimino-3-(1,2,3,4,5-penta-O-acetylpentitol-1-yl)benzofuran-4(2H)one 
• 110545-25-0 (3S)-3-(1,2,3,4,5-penta-O-acetyl-D-galacto-pentitol-1-yl)-1,2,3,5,6,7-hexahydroindol-4-one 
• 110545-25-0 Acetic acid (1S,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-((S)-4-oxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)-pentyl ester 
• 35768-38-8 3-hydroxy-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 36555-52-9 glyoxal monoxime 
• 879214-86-5 3-[(2,2-diethoxyethyl)amino]cyclohex-2-en-1-one 
• 392232-66-5 benzyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate 

Downstream Products

• 2380-94-1 1H-indol-4-ol 
• 5192-23-4 4-amino-1H-indole 
• 14006-77-0 2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one 
• 13671-74-4 1-benzyl-4-oxo-4,5,6,7-tetrahydroindole 
• 1349368-76-8 ethyl 1-[(4-methylbenzene)sulfonyl]-4,5,6,7-tetrahydro-1H-indole-4-carboxylate 
• 106486-93-5 1-[(4-methylbenzene)sulfonyl]-6,7-dihydro-1H-indole-4-carbonitrile 
• 106154-13-6 1-[(4-methylbenzene)sulfonyl]-4-[(trimethylsilyl)oxy]-4,5,6,7-tetrahydro-1H-indole-4-carbonitrile 
• 1332584-12-9 tert-butyl 4-oxooctahydro-1H-indole-1-carboxylate 
• 1932405-48-5 octahydropyrrolo[3,2-b]azepin-5(1H)one 
• 1821237-04-0 tert-butyl 4-hydroxyoctahydro-1H-indole-1-carboxylate 
• 51471-08-0 1-methyl-1,5,6,7-tetrahydro-indol-4-one 

Relevant articles and documents

ISOQUINOLINESULFONYL DERIVATIVE AS RHO KINASE INHIBITOR

The present invention discloses a class of isoquinolinesulfonyl derivatives as RHO kinase inhibitors, and pharmaceutical compositions thereof, and relates to pharmaceutically acceptable uses thereof. Specifically, the present invention relates to a compound as represented by formula (I), or a pharmaceutically acceptable salt thereof.

Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: A mechanistic interpretation and conversion into 4- and 7-oxoindoles

An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7- tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.

Tricyclic indole and dihydroindole derivatives as new inhibitors of soluble guanylate cyclase

The synthesis of new tricyclic fused indole and dihydroindole derivatives and preliminary results from their in vitro inhibitory activity against soluble guanylate cyclase (sGC) are presented.