184422-85-3

Basic information

• Product Name: 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one
• Synonyms: 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one
• CAS NO: 184422-85-3
• Molecular Weight: 279.36
• Mol File: 184422-85-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one(184422-85-3)
• EPA Substance Registry System: 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one(184422-85-3)

Safety Data

• Hazardous Substances Data: 184422-85-3(Hazardous Substances Data)

Upstream product

• 171111-15-2 4-ethyl-3-methyl-2-(p-toluenesulfonyl)-1H-pyrrole 
• 89896-01-5 3-nitropentan-2-ol acetate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 31837-49-7 tert-Butyl 4-Ethyl-5-iodo-3-methylpyrrole-2-carboxylate 
• 536-57-2 p-toluene sulfinic acid 
• 263898-72-2 5-acetoxy-5-(t-butoxycarbonyl)-3-ethyl-1,5-dihydro-4-methyl-2H-pyrrol-2-one 
• 226223-25-2 2-bromo-3-ethyl-4-methyl-5-p-toluenesulfonyl-pyrrole 
• 184422-74-0 3-Ethyl-2-iodo-4-methyl-5-(toluene-4-sulfonyl)-1H-pyrrole 
• 184422-60-4 3-Ethyl-4-methyl-5-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 184422-66-0 3-Ethyl-4-methyl-5-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 76367-42-5 ethyl 5-carboxy-3-ethyl-5-iodo-4-methylpyrrole-2-carboxylate 
• 4949-58-0 2-(ethyloxycarbonyl)-3-ethyl-4-methylpyrrole 

Downstream Products

• 16883-97-9 phycocyanobilin 
• 766-36-9 3-ethyl-4-methyl-3-pyrrolin-2-one 

Relevant articles and documents

Synthesis and properties of mesobilirubins XIIγ and XIIIγ and their mesobiliverdins

The title pigments, with propionic acid groups displaced to the lactam end rings, were synthesized for the first time by the "1 + 2 + 1" approach, coupling two equivalents of a monopyrrole to a dipyrrylmethane (to give XIIγ), or the "2 + 2" approach, self-coupling two equivalents of a dipyrrinone (to give XIIIγ). Using the "1 + 2 + 1" approach, mesobilirubin IIIα was also prepared. Mesobilirubins XIIγ and XIIIγ are more polar than mesobilirubin IIIα and unlike IIIα cannot effectively engage the propionic acid groups in intramolecular hydrogen bonding to the dipyrrinone components. The new mesobilirubins give exciton coupled circular dichroism spectra in the presence of human serum albumin or quinine, with the XIIγ isomer exhibiting Cotton effect intensities nearly as strong as those from the IIIα isomer; whereas, the XIIIγ isomer exhibits far weaker intensities. Mesobilirubin IIIα requires glucuronidation for hepatobiliary elimination; whereas, XIIγ and XIIIγ do not, and they are excreted intact across the liver into bile. The corresponding biliverdins XIIγ and XIIIγ are reduced only slowly by biliverdin IXα reductase, in contrast to the fast reduction of the natural IXα isomer. Graphical abstract: [Figure not available: see fulltext.]

An efficient method to construct the A,B-rings component toward total syntheses of phycocyanobilin and its derivative as a photoprobe

Total syntheses of physocyanobilin and its derivative bearing a photoreactive group at the D-ring accomplished by developing a new and efficient method for the construction of A,B-rings component, which consists of the Wittig-type new coupling reaction of 4-(1-methoxyethyl or 1- tosylethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one and a 2-formyl pyrrole derivative in the presence of (n)Bu3P and a base, followed by reduction with aluminum amalgam and a subsequent acid or base treatment.

Syntheses of 3,4-disubstituted 2-tosylpyrroles and 5-tosyl-1,5-dihydro-2H-pyrrol-2-ones starting from ethyl 3,4-disubstituted 2-pyrrolecarboxylates

The syntheses of 3,4-disubstituted 2-tosylpyrroles and 5-tosyl-1,5-dihydro-2H-pyrrol-2-ones were accomplished via 3,4-disubstituted 2-iodo-5-tosylpyrroles starting from ethyl 3,4-disubstituted 2-pyrrolecarboxylates.