112970-70-4

Basic information

• Product Name: 1H-Indole, 6-ethenyl-1-[(4-methylphenyl)sulfonyl]-
• Synonyms: 1-(Toluene-4-sulfonyl)-6-vinyl-1H-indole;6-vinyl-N-tosylindole
• CAS NO: 112970-70-4
• Molecular Formula: C17H15NO2S
• Molecular Weight: 297.37200
• Mol File: 112970-70-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 490.7±48.0 °C(Predicted)
• Density: 1.18±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Indole, 6-ethenyl-1-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 6-ethenyl-1-[(4-methylphenyl)sulfonyl]-(112970-70-4)
• EPA Substance Registry System: 1H-Indole, 6-ethenyl-1-[(4-methylphenyl)sulfonyl]-(112970-70-4)

Safety Data

• Hazardous Substances Data: 112970-70-4(Hazardous Substances Data)

Usage

Molecular structure

A derivative of indole with a sulfonyl group attached to a 4-methylphenyl ring and an ethenyl group at the 6-position.

Type of compound

Heterocyclic aromatic organic compound

Sulfonyl group

Attached to a 4-methylphenyl ring at the 1-position of the indole ring

Ethenyl group

Located at the 6-position of the indole ring

Potential applications

Organic synthesis and pharmaceutical research

Unique features

Structural features and potential biological activities

Further research

Needed to fully understand and exploit its potential uses

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 50820-65-0 indole-6-carboxylic acid methyl ester 
• 184579-89-3 1-[(4-methylbenzene)sulfonyl]-1H-indole-6-carbaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 112970-58-8 2,5-dibromo-N-tosylaniline 
• 3638-73-1 2,5-dibromoaniline 
• 112970-60-2 2,5-divinyl-N-tosylaniline 

Downstream Products

• 1365987-41-2 (S)-6-(but-3-en-2-yl)-1-(toluene-4-sulfonyl)-1H-indole 

Relevant articles and documents

Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B

Vinylindoles undergo Ni(II)-catalyzed asymmetric hydrovinylation under very mild conditions (-78 °C, 1 atm ethylene, 4 mol % catalyst) to give the corresponding 2-but-3-enyl derivatives in excellent yields and enantioselectivities. Hydroboration of the alkene and oxidation to an acid, followed by Friedel-Crafts annulation, gives an indole-annulated cyclopentanone that is a suitable precursor for the syntheses of cis-trikentrins and all known herbindoles. For example, the cyclopentanone from 4-ethyl-7-vinylindole is converted into (+)-cis-trikentin A in four steps (Wittig reaction, alkene isomerization, diastereoselective hydrogenation, and nitrogen deprotection). The previous synthesis of this molecule from (S)-(-)-malic acid involved more than 20 steps and a preparative HPLC separation of diastereomeric intermediates.