78318-00-0

Basic information

• Product Name: 3-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE
• Synonyms: 3-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE
• CAS NO: 78318-00-0
• Molecular Formula: C₁₅H₁₅N
• Molecular Weight: 209.29
• Mol File: 78318-00-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE(78318-00-0)
• EPA Substance Registry System: 3-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE(78318-00-0)

Safety Data

• Hazardous Substances Data: 78318-00-0(Hazardous Substances Data)

Upstream product

• 729-43-1 acetophenonazine 
• 135365-20-7 3,4-dihydro-3-phenylisoquinoline 
• 2674-44-4 3-phenyl-isochroman-1-one 
• 4809-08-9 3-phenyl-isocoumarin 
• 7115-13-1 3-phenyl-2H-isoquinolin-1-one 
• 100-52-7 benzaldehyde 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 321526-76-5 2-(2-amino-2-phenylethyl)phenylmethanol 
• 64-17-5 ethanol 
• 55150-55-5 1,4-dichloro-3-phenyl-isoquinoline 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 146530-25-8 2-formyl-1,2,3,4-tetrahydro-3-phenylisoquinoline 

Downstream Products

• 85741-16-8 2-Nitroso-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 135365-20-7 3,4-dihydro-3-phenylisoquinoline 
• 85741-19-1 [1-(4-Nitro-phenyl)-meth-(E)-ylidene]-(3-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-amine 
• 85741-17-9 2-amino-3-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Relevant articles and documents

Regioselective Lithiation and Electrophilic Quenching of N-Boc-3-phenyltetrahydroisoquinoline

Tetrahydroisoquinolines are found in many natural products and drug compounds and a convenient method to access 1-substituted derivatives is to carry out the lithiation at C-1 followed by trapping with an electrophile. Here we explore the feasibility of lithiation at C-3 by using a substrate with a benzylic proton on both sides of the nitrogen atom such that lithiation with nBuLi could occur at either C-1 or C-3 of the tetrahydroisoquinoline. The regioselectivity in the lithiation was determined using the substrate N-tert-butoxycarbonyl (Boc)-3-phenyltetrahydroisoquinoline. The lithiation could be followed by in situ ReactIR spectroscopy and the rate of rotation of the carbamate group was determined (barrier to rotation was approximately ΔG? 58 kJ/mol at –50 °C). Subsequent trapping of the organolithium species with an electrophile gave a mixture of two regioisomeric products with a preference for reaction at C-1. This led to the isolation of 1,3-disubstituted tetrahydroisoquinolines with trans relative stereochemistry. Removal of the Boc group from the nitrogen atom gave secondary and tertiary amine products.

Use of the N-formyliminium ion cyclization for the synthesis of 3-aryl-1,2,3,4-tetrahydroisoquinolines

Classical cyclization procedures for the synthesis of 3-arylisoquinolines are fraught with complications. Here, we present the application of an N-acyliminium cyclization to such target molecules. N(1,2-diarylethyl)formamides 1, 4a-4d, and 4f were cyclize

THERMAL HETEROCYCLIZATION OF METHYL ARYL KETAZINES. REACTIONS OF THE TAUTOMERIC ENEHYDRAZINE FORM

Over the temperature range 220-280 deg C the thermal reactions of methyl aryl ketazines (Ar=C6H5-, 4-CH3C6H4-, 4-CH3OC6H4-, and α-naphthyl-) proceed with their cyclization to give pyrazoline and benzodiazepine derivatives.With an increase in temperature to 320-350 deg C the subsequent transformations of these compounds lead to the formation of substituted pyrazoles, 1-methyl-1,2-diarylcyclopropanes isomeric olefins, low-molecular-weight aromatic hydrocarbons, and isoquinolines.