136905-00-5

Basic information

• Product Name: (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 136905-00-5
• Molecular Weight: 269.343
• Mol File: 136905-00-5.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(136905-00-5)
• EPA Substance Registry System: (S)-(-)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline(136905-00-5)

Safety Data

• Hazardous Substances Data: 136905-00-5(Hazardous Substances Data)

Upstream product

• 4029-09-8 6,7-dimethoxy-1-phenyl-isoquinoline 
• 20922-03-6 1-(propan-2-yl)isoquinoline 
• 4118-36-9 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 98-88-4 benzoyl chloride 
• 1643770-97-1 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-methoxy-2-phenylacetate 
• 1417826-99-3 (S)-1-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-pent-4-en-1-one 
• 922359-27-1 1-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pent-4-en-1-one 
• 67616-16-4 N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide 
• 100-52-7 benzaldehyde 
• 10172-51-7 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 

Downstream Products

• 4118-36-9 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-67-6 (+)-2-(hept-6-ynyl)-6,7-dimethoxy-1S-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-69-8 (+)-6,7-dimethoxy-2-(oct-7-ynyl)-1S-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Asymmetric transfer hydrogenation of 1-phenyl dihydroisoquinolines using Ru(II) diamine catalysts

A new [Ru(II)(η6-p-cymene)(1R,2R)-N-((1S,2S)-borneol-10- sulfonyl)-1,2-diphenylethylenediamine] catalyst for the asymmetric transfer hydrogenation of both 1-alkyl and 1-aryl dihydroisoquinolines has been isolated. For the first time in this type of reaction, the catalyst employs an N-alkylsulfonyl group instead of N-arylsulfonyl.

Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity

The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.

Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.