135365-21-8

Basic information

• Product Name: 1-methyl-3-phenyl-3,4-dihydroisoquinoline
• Synonyms: 1-methyl-3-phenyl-3,4-dihydroisoquinoline
• CAS NO: 135365-21-8
• Molecular Weight: 221.302
• Mol File: 135365-21-8.mol

Chemical Properties

• CAS DataBase Reference: 1-methyl-3-phenyl-3,4-dihydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3-phenyl-3,4-dihydroisoquinoline(135365-21-8)
• EPA Substance Registry System: 1-methyl-3-phenyl-3,4-dihydroisoquinoline(135365-21-8)

Safety Data

• Hazardous Substances Data: 135365-21-8(Hazardous Substances Data)

Upstream product

• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 62-53-3 aniline 
• 100-42-5 styrene 
• 613-91-2 acetophenone oxime 
• 1128111-86-3 7-methyl-N-[(1E)-phenylmethylene]bicyclo[4.2.0]octa-1,3,5-trien-7-amine 
• 21511-90-0 N-(1,2-diphenylethyl)acetamide 
• 135365-09-2 cis-6,10b-dihydro-10b-methyl-5-phenyl-5H-oxazolo<2,3-a>isoquinoline-2,3-dione 

Downstream Products

• 1721-96-6 1-methyl-3-phenylisoquinoline 
• 135365-22-9 (R)-3,4-dihydro-1-methyl-3-phenylisoquinoline 

Relevant articles and documents

The photoredox-catalyzed meerwein addition reaction: Intermolecular amino-arylation of alkenes

A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of a 3-aryl-3,4- dihydroisoquinoline. From elimination to addition: A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of 3-aryl-3,4-dihydroisoquinoline. Copyright

Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes

Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl 2 ] 2 (2.5 molpercent; Cp? = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the corresponding substituted dihydroisoquinolines in yields of 50-99percent. On the other hand, alkenes containing functional groups close to the double bond gave a variety of different products. The reactions of acetophenone oxime with styrene or dec-1-ene in the presence of the chiral catalyst [(C 5 H 2 t Bu 2 CH 2 t Bu)RhI 2 ] 2 provided the corresponding dihydroisoquinolines with improved regioselectivity but a low enantiomeric ratio (61:39 in both cases).

Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: Total synthesis of coralydine

(Chemical Equation Presented) Thanks to C-H activation: 3-Aryl-3,4-dihydroisoquinolines (2) are synthesized from bromobenzenes (1) by a sequence comprising a C(sp3)-H activation, a Curtius rearrangement, and a tandem electrocyclic ring-opening/

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.