3340-78-1

Usage

Uses

Used in Chemical Synthesis:
2-Phenyl-1,2,3,4-tetrahydroisoquinoline is used as a reactant in acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at the α-position of tertiary amines. This application is significant as it allows for the creation of new carbon-carbon bonds without the need for metal catalysts, which can be advantageous in terms of cost, environmental impact, and reaction conditions.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, due to its structural similarity to various bioactive compounds, could potentially be used in the pharmaceutical industry as a starting material or intermediate for the synthesis of drugs targeting specific receptors or enzymes. Its reactivity and structural features make it a promising candidate for the development of novel therapeutic agents.

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 3076-54-8 phenyllead(IV) triacetate 
• 603-33-8 triphenylbismuthane 
• 38256-56-3 1-(2-bromo-ethyl)-2-bromomethyl-benzene 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 493-05-0 isochromane 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 124525-61-7 1-(1,2,3,7-tetrahydro-2-isoquinolinyl)benzaldehyde 
• 446-52-6 2-Fluorobenzaldehyde 
• 103-69-5 N-ethyl-N-phenylamine 
• 325723-04-4 Phenylbiphenyl-2,2'-ylenebismuth diacetate 
• 78317-77-8 N-Methyl-N-phenyl-1,2,3,4-tetrahydroisochinoliniumiodid 

Downstream Products

• 55662-89-0 2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 78317-77-8 N-Methyl-N-phenyl-1,2,3,4-tetrahydroisochinoliniumiodid 
• 59224-75-8 1-(4-methoxyphenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1048958-12-8 1-(biphenyl-4-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 13355-49-2 1-(4-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)ethanone 
• 1048958-19-5 1-(4-(tert-butyl)phenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1048958-13-9 1-(4-(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)ethanone 

Relevant academic research and scientific papers

The Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines: Comprehensive Mechanism, H?- versus H+-Abstraction, and Background Reactions

The cross-dehydrogenative coupling (CDC) reaction of N-aryltetrahydroisoquinolines (THIQ) is one of the most exploited photocatalytic transformation and a test reaction for an exceptional variety of catalysts. However, its mechanism remained unclear conce

CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds

A novel and efficient C-C bond formation method was developed via the cross-dehydrogenative coupling (CDC) reaction of indoles and tetrahydroisoquinolines catalyzed by copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct indolyl tetrahydroisoquinolines via a combination of sp3 C-H bond and sp2 C-H bond followed by C-C bond formation. Copyright

Direct Near Infrared Light–Activatable Phthalocyanine Catalysts

The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

N-Phenyl-1,2,3,4-tetrahydroisoquinoline: An Alternative Scaffold for the Design of 17β-Hydroxysteroid Dehydrogenase 1 Inhibitors

17β-Hydroxysteroid dehydrogenases catalyse interconversion at the C17 position between oxidized and reduced forms of steroidal nuclear receptor ligands. The type 1 enzyme, expressed in malignant cells, catalyses reduction of the less-active estrone to estradiol, and inhibitors have therapeutic potential in estrogen-dependent diseases such as breast and ovarian cancers and in endometriosis. Synthetic decoration of the nonsteroidal N-phenyl-1,2,3,4-tetrahydroisoquinoline (THIQ) template was pursued by using Pomeranz-Fritsch-Bobbitt, Pictet-Spengler and Bischler-Napieralski approaches to explore the viability of this scaffold as a steroid mimic. Derivatives were evaluated biologically in vitro as type 1 enzyme inhibitors in a bacterial cell homogenate as source of recombinant protein. Structure-activity relationships are discussed. THIQs possessing a 6-hydroxy group, lipophilic substitutions at the 1- or 4-positions in combination with N-4′-chlorophenyl substitution were most favourable for activity. Of these, one compound had an IC50 of ca. 350 nM as a racemate, testifying to the applicability of this novel approach.

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

Effect of Precatalyst Oxidation State in C-N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes

We report the catalytic activity of two phosphinoimidazole-derived bimetallic palladium complexes in Pd-catalyzed amination reactions. Our studies demonstrate that the starting oxidation state (Pd(I) or Pd(II)) of the dimeric complex has a significant effect on the efficiency of the catalytic reaction. The corresponding Pd(I) complex shows higher reactivity in Buchwald-Hartwig aminations, while the Pd(II) complex is much more reactive in carbonylative amination reactions. These new dimeric palladium complexes provide good to excellent reactivity and yields in the amination reactions tested.

Electrocatalytic C(sp3)-H/C(sp)-H cross-coupling in continuous flow through TEMPO/copper relay catalysis

Electrocatalytic dehydrogenative C(sp3)-H/C(sp)-H cross-coupling of tetrahydroisoquinolines with terminal alkynes has been achieved in a continuous-flow microreactor through 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/copper relay catalysis. The reaction

Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones

Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.