888504-80-1

Basic information

• Product Name: 1-[(4-methoxyphenyl)sulfonyl]-1H-3-indole-3-acetic acid
• Synonyms: 1-[(4-methoxyphenyl)sulfonyl]-1H-3-indole-3-acetic acid
• CAS NO: 888504-80-1
• Molecular Formula: C₁₇H₁₅NO₅S
• Molecular Weight: 345.37
• Mol File: 888504-80-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-[(4-methoxyphenyl)sulfonyl]-1H-3-indole-3-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(4-methoxyphenyl)sulfonyl]-1H-3-indole-3-acetic acid(888504-80-1)
• EPA Substance Registry System: 1-[(4-methoxyphenyl)sulfonyl]-1H-3-indole-3-acetic acid(888504-80-1)

Safety Data

• Hazardous Substances Data: 888504-80-1(Hazardous Substances Data)

Upstream product

• 87-51-4 indole-3-acetic acid 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 

Downstream Products

• 123843-22-1 methyl N-(p-methoxybenzenesulfonyl)-3-indoleacetate 
• 1391630-44-6 2-[1-(4-methoxyphenylsulfonyl)-1H-indol-3-yl]N-(benzothiazol-2-yl)acetamide 
• 123843-23-2 N-(p-methoxybenzenesulfonyl)-3-indoleacetaldehyde 
• 888504-85-6 (αR,1S.7S)-7,7-dimethoxy-2-{{1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}acetyl}-2-azabicyclo[2.2.2]octan-6-methanol acetate 
• 888504-83-4 (αR,1S,6S,7S)-7-hydroxy-{{1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}acetyl}-2-azabicyclo[2.2.2]ctane-6-methanol α-acetate 
• 888504-84-5 (1S,7S)-7-[(1R)-1-(acetyloxy)ethyl]-{{1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}acetyl}-2-azabicyclo[2.2.2]octane-6-one 
• 888504-81-2 (αR,1S,6S,7S)-7-(benzyloxy)-2-{{1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}acetyl}-2-azabicyclo[2.2.2]octane-6-methanol acetate 

Relevant articles and documents

Enantioselective synthesis of (-)-(19R)-ibogamin-19-ol

The first total synthesis of the natural product (-)-(19R)-ibogamin-19-ol ((-)-1) is reported (biogenetic atom numbering). Starting with L-glutamic acid from the chiral pool and (2S)-but-3-en-2-ol, the crucial aliphatic isoquinuclidine (=2-azabicyclo[2.2.2]octane) core containing the entire configurational information of the final target was prepared in 15 steps (overall yield: 15%). The two key steps involved a highly effective, self-immolating chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone-olefin 1,3-dipolar cycloaddition reaction (Scheme 3). Onto this aliphatic core was grafted the aromatic moiety in the form of N(1)-protected 1H-indole-3-acetic acid by application of the dicyclohexylcarbodiimide (DCC) method (Scheme 4). Four additional steps were required to adjust the substitution pattern at C(16) and to deprotect the indole subunit for the closure of the crucial 7-membered ring present in the targeted alkaloid family (Schemes 4 and 5). The spectral and chiroptical properties of the final product (-)-1 matched the ones reported for the naturally occurring alkaloid, which had been isolated from Tabernaemonatana quadrangularis in 1980. The overall yield of the entire synthesis involving a linear string of 20 steps amounted to 1.9% (average yield per step: 82%).