233606-26-3

Basic information

• Product Name: 3H-Cyclopent[c]isoxazole,3a,4,5,6-tetrahydro-6-(2-thienyl)-,(3aR,6R)-rel-(9CI)
• Synonyms: 3H-Cyclopent[c]isoxazole,3a,4,5,6-tetrahydro-6-(2-thienyl)-,(3aR,6R)-rel-(9CI)
• CAS NO: 233606-26-3
• Molecular Formula: C10H11NOS
• Molecular Weight: 193.26544
• Product Categories: CYCLOPENTANE
• Mol File: 233606-26-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3H-Cyclopent[c]isoxazole,3a,4,5,6-tetrahydro-6-(2-thienyl)-,(3aR,6R)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Cyclopent[c]isoxazole,3a,4,5,6-tetrahydro-6-(2-thienyl)-,(3aR,6R)-rel-(9CI)(233606-26-3)
• EPA Substance Registry System: 3H-Cyclopent[c]isoxazole,3a,4,5,6-tetrahydro-6-(2-thienyl)-,(3aR,6R)-rel-(9CI)(233606-26-3)

Safety Data

• Hazardous Substances Data: 233606-26-3(Hazardous Substances Data)

Relevant articles and documents

One-pot synthesis of five- or six-membered carbocycles through intramolecular cycloadditions by the use of ethyl chloroformate

The Michael addition reactions of β-nitrostyrenes 1 with 4-pentene-1- magnesium bromide 2a or 3-butene-1-magnesium bromide 2b generated nitronates 3 or 4. Medium to high yields of isoxazolidine derivatives 9 and 10 were obtained when nitronates 3 or 4 were treated with ethyl chloroformate and catalytic amount of 4-dimethylaminopyridine (DMAP) at room temperature in one-pot and the ratios of trans-9:cis-9 were from 1:3.00 to 1:4.06 and the ratios of trans-10:cis-1 0 were >99:1. The formation of compounds 9 is proposed to proceed through intramolecular nitrile oxide-olefin cycloadditions (INOC) because compounds 14a-d, obtained from the trapping of the nitrile oxides by ethyl chloroformate, could be isolated. The mechanism of the generation of compounds 10 is proposed to proceed through intramolecular alkoxycarbonyl nitronate-olefin cycloadditions (IAOC) to form intermediates N-(ethoxycarbonyl)isoxazolidines 13 and then eliminate EtOH and CO2 (or EtOCO2H) to yield the final products.