1423754-18-0

Basic information

• Product Name: (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal
• Synonyms: (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal
• CAS NO: 1423754-18-0
• Molecular Weight: 462.954
• Mol File: 1423754-18-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal(1423754-18-0)
• EPA Substance Registry System: (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal(1423754-18-0)

Safety Data

• Hazardous Substances Data: 1423754-18-0(Hazardous Substances Data)

Upstream product

• 17422-33-2 6-chloroindole 
• 703-82-2 6-chloro-1H-indole-3-carbaldehyde 
• 110-62-3 pentanal 
• 1423754-12-4 C₁₇H₁₃ClN₂O₄S 

Relevant articles and documents

Organocatalytic asymmetric Michael addition of aliphatic aldehydes to indolylnitroalkenes: Access to contiguous stereogenic tryptamine precursors

Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1- ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.