21638-57-3

Basic information

• Product Name: N-(2,2-dimethoxyethyl)-1-(3,4-dimethoxyphenyl)but-3-en-1-amine
• Synonyms: N-(2,2-dimethoxyethyl)-1-(3,4-dimethoxyphenyl)but-3-en-1-amine
• CAS NO: 21638-57-3
• Molecular Weight: 295.379
• Mol File: 21638-57-3.mol

Chemical Properties

• CAS DataBase Reference: N-(2,2-dimethoxyethyl)-1-(3,4-dimethoxyphenyl)but-3-en-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,2-dimethoxyethyl)-1-(3,4-dimethoxyphenyl)but-3-en-1-amine(21638-57-3)
• EPA Substance Registry System: N-(2,2-dimethoxyethyl)-1-(3,4-dimethoxyphenyl)but-3-en-1-amine(21638-57-3)

Safety Data

• Hazardous Substances Data: 21638-57-3(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 805323-20-0 N-[(1E)-(3,4-dimethoxyphenyl)methylene]-2,2-dimethoxyethanamine 

Relevant articles and documents

Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization

Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQ) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products.