29903-68-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 501-52-0 3-Phenylpropionic acid 
• 2878-60-6 N-(3,4-dimethoxyphenethyl)-3-phenylpropanamide 
• 81305-67-1 3,4-dihydro-6,7-dimethoxy-1-(2-phenylethyl)isoquinoline 
• 645-45-4 hydrocinnamic acid chloride 
• 10147-11-2 propargyl benzene 

Downstream Products

• 17578-66-4 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet-Spengler reaction

Norcoclaurine synthase (NCS) catalyzes the stereo-selective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as the first step of benzylisoquinoline alkaloid synthesis in plants. Recent studies suggested that NCS shows relatively relaxed substrate specificity toward aldehydes, and thus, the enzyme can serve as a tool to synthesize unnatural, optically active tetrahydroisoquinolines. In this study, using an N-terminally truncated NCS from Coptis japonica expressed in Escherichia coli, we examined the aldehyde substrate specificity of the enzyme. Herein, we demonstrate the versatility of the enzyme by synthesizing 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline and 6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline in molar yields of 86.0 and 99.6% and in enantiomer excess of 95.3 and 98.0%, respectively. The results revealed the enzyme is a promising catalyst that functions to stereoselectively produce various 1-substituted-1,2,3,4-tetrahydroisoquinolines.

Synthesis and structure activity relationship of tetrahydroisoquinoline- based potentiators of GluN2C and GluN2D containing N-Methyl-D-aspartate receptors

We describe here the synthesis and evaluation of a series of tetrahydroisoquinolines that show subunit-selective potentiation of NMDA receptors containing the GluN2C or GluN2D subunits. Bischler-Napieralski conditions were employed in the key step for the

An easy-to-use, regioselective, and robust bis(amidate) titanium hydroamination precatalyst: Mechanistic and synthetic investigations toward the preparation of tetrahydroisoquinolines and benzoquinolizine alkaloids

Amidate-supported titanium amido complexes are efficient and regioselective precatalysts for intermolecular hydroamination of terminal alkynes with primary amines. The synthesis and characterization of the first his(amidate)-supported titanium-imido complex is reported. Its role as the active catalytic species is suggested in the course of product distribution studies using deuteratcd substrates. The bis(amidate)-supported prccatalysts exhibit good functional-group tolerance, even performing hydroaminations in the presence of ester and amide groups. This functional-group tolerance was exploited in the synthesis of a variety of 1-substituted tetrahydroisoquinoline alkaloids and a one-pot hydroaminative procedure for the high yielding preparation of the benzo[a]quinolizine skeleton.

Tetrahydroisoquinoline derivatives as melatonin MT2 receptor antagonists

A series of tetrahydroisoquinolines has yielded potent MT2 receptor antagonists, which are selective versus the MT1 receptor. A series of tetrahydroisoquinolines has yielded potent MT2 receptor antagonists, which are selective versus the MT1 receptor.