222533-63-3

Usage

General Description

1H-Indole-3-acetic acid, 2,3-dihydro-3-(3-methyl-2-butenyl)-2-oxo-1-(phenylmethyl)-, (3S)- is a naturally occurring plant hormone that plays a crucial role in regulating various physiological processes in plants, including cell division, growth, and development. This chemical compound, also known as Indole-3-acetic acid (IAA), is involved in the regulation of plant growth and responses to environmental cues such as light, gravity, and stress. It is also used in agricultural practices as a growth regulator to stimulate root development, increase fruit setting, and improve crop yields. In addition to its role in plant growth and development, IAA has been studied for its potential pharmaceutical applications, including its anti-inflammatory and anti-tumor properties.

Upstream product

• 1161443-56-6 trimethyl{(5R)-5-methyl-5-[(trimethylsilyl)oxy]hept-6-en-1-yn-1-yl}silane 
• 1161443-55-5 (3R)-3-methylhept-1-en-6-yn-3-ol 
• 126-91-0 linalool 
• 100-52-7 benzaldehyde 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 615-43-0 2-iodophenylamine 
• 222533-60-0 1-benzyl-3-(3-methylbut-2-enyl)-1,3-dihydroindol-2-one 
• 870-63-3 prenyl bromide 
• 222533-62-2 (S)-1-benzyl-3-(3-methylbut-2-enyl)-3-(2-nitroethyl)-2-oxindole 
• 7135-32-2 1-benzylindolin-2-one 
• 222533-61-1 (S)-1-benzyl-3-(3-methylbut-2-enyl)-3-(2-nitrovinyl)-2-oxindole 

Downstream Products

• 222533-64-4 (S)-1-benzyl-3-(3-methylbut-2-enyl)-3-(benzyloxycarbonylaminomethyl)-2-oxindole 
• 1380585-92-1 (3aS,8aR)-8-benzyl-1-methyl-3a-(3-methylbut-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 222533-65-5 (R)-1-benzyl-3-(hydroxymethyl)-3-(3-benzyloxycarbonylaminomethyl)-2-oxindole 
• 222533-68-8 (R)-1-benzyl-1'-benzyloxycarbonyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine) 
• 222533-66-6 (3R)-1-benzyl-1'-benzyloxycarbonyl-2'-hydroxy-2-oxospiro(3H-indole-3,4'-pyrrolidine) 
• 222533-67-7 (R)-1-benzyl-1'-benzyloxycarbonyl-2-oxospiro(3H-indole-3,4'-pyrrolidine) 
• 222533-59-7 (R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine) 

Relevant academic research and scientific papers

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid

An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.

Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine

A versatile route to enantiopure 3,3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is described in which diastereoselective dialkylation of enantiopure ditriflate 10 with oxindole enolates is the central step. These reactions are rare examples of alkylations of prostereogenic enolates with chiral sp3 electrophiles that proceed with high facial selectivity (10-20:1). The scope of this method is explored, and a model to rationalize the sense of stereoselection is advanced. This dialkylation chemistry was used to synthesize (-)-phenserine on a multigram scale in six steps and 43% overall yield from 5-methoxy-1,3-dimethyloxindole (27) and to complete a short formal total synthesis of (-)-physostigmine (2).