327187-97-3

Basic information

• Product Name: 2H-Isoxazolo[3,2-a]isoquinoline,2-ethoxy-1,5,6,10b-tetrahydro-,(2S,10bS)-(9CI)
• Synonyms: 2H-Isoxazolo[3,2-a]isoquinoline,2-ethoxy-1,5,6,10b-tetrahydro-,(2S,10bS)-(9CI)
• CAS NO: 327187-97-3
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.28
• Product Categories: ETHOXY
• Mol File: 327187-97-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Isoxazolo[3,2-a]isoquinoline,2-ethoxy-1,5,6,10b-tetrahydro-,(2S,10bS)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Isoxazolo[3,2-a]isoquinoline,2-ethoxy-1,5,6,10b-tetrahydro-,(2S,10bS)-(9CI)(327187-97-3)
• EPA Substance Registry System: 2H-Isoxazolo[3,2-a]isoquinoline,2-ethoxy-1,5,6,10b-tetrahydro-,(2S,10bS)-(9CI)(327187-97-3)

Safety Data

• Hazardous Substances Data: 327187-97-3(Hazardous Substances Data)

Upstream product

• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 109-92-2 ethyl vinyl ether 

Relevant articles and documents

Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid

A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1 H and 31 P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

Catalytic enantioselective 1,3-dipolar cycloaddition reactions of cyclic nitrones: A simple approach for the formation of optically active isoquinoline derivatives

The first highly diastereo- and enantioselective catalytic 1,3-dipolar cycloaddition reaction of cyclic nitrones activated by chiral Lewis acids with electron-rich alkenes has been developed. The nitrones, mainly 3,4-dihydroisoquinoline N-oxides, are activated by chiral 3,3′-aryl BINOL-AlMe complexes and undergo a regio-, diastereo-, and enantioselective 1,3-dipolar cycloaddition reaction with especially alkyl vinyl ethers, giving the exo diastereomer of the cycloaddition products in high yield, >90% de and up to 85% ee. The reaction has been investigated under various conditions, and it is demonstrated that the reaction is an attractive synthetic procedure for the introduction of a chiral center in the 1-position of the isoquinoline skeleton. The mechanism of the reaction is discussed on the basis of the assignment of the absolute configuration of the cycloaddition product and theoretical calculations.

Palladium(II)-catalyzed 1,3-dipolar cycloaddition of nitrones with enol ethers

The 1,3-dipolar cycloadditions of enol ethers as electron-rich olefins with C-phenyl-N-alkyl nitrones proceeded smoothly in the presence of easy handling palladium(II) catalysts under mild conditions to give isoxazolidines in good yield.

1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines

The 1,3-dipolar cycloaddition reactions of various Z- and E-nitrones with ethyl vinyl ether and 2,3-dihydrofuran are catalyzed by 20 mol% of chiral oxazaborolidines at room temperature. The effect of high pressure on these reactions is discussed.