78317-83-6

Basic information

• Product Name: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-
• Synonyms: N-PMP-1,2,3,4-tetrahydroisoquinoline;N-p-methoxyphenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 78317-83-6
• Molecular Formula: C16H17NO
• Molecular Weight: 239.317
• Mol File: 78317-83-6.mol

Chemical Properties

• Melting Point: 91-94°C
• CAS DataBase Reference: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-(78317-83-6)
• EPA Substance Registry System: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-(78317-83-6)

Safety Data

• Hazardous Substances Data: 78317-83-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)is used as a reagent in the gold-catalyzed preparation of indoletetrahydroisoquinolines. This application takes advantage of the compound's unique structure and reactivity, enabling the synthesis of complex organic molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
Isoquinoline, 1,2,3,4-tetrahydro-2-(4-methoxyphenyl)may also find use in the pharmaceutical industry as a building block for the development of new drugs. Its unique structure and functional groups can be utilized in the design and synthesis of novel therapeutic agents, potentially leading to the discovery of new treatments for various diseases and conditions.

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 850130-96-0 2-(4-methoxyphenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 
• 102-96-5 (2-nitroethenyl)benzene 
• 100-52-7 benzaldehyde 
• 64-04-0 phenethylamine 
• 493-05-0 isochromane 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 104-94-9 4-methoxy-aniline 
• 100-66-3 methoxybenzene 
• 105728-90-3 2-fluoro-5-methoxybenzaldehyde 
• 356531-15-2 N-(4-methoxyphenyl)-2-bromobenzylamine 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 850130-96-0 2-(4-methoxyphenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 
• 1048958-15-1 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1048958-16-2 1-(biphenyl-4-yl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1048958-18-4 2-(4-methoxyphenyl)-1-(naphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline 
• 1048958-20-8 1-(4-tert-butylphenyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1048958-17-3 1-(4-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)ethanone 
• 1048958-14-0 1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1141447-85-9 1-[1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-1-isoquinolinyl]hexan-2-one 
• 1141447-88-2 2-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-1-phenylethan-1-one 
• 1141447-90-6 2-[1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-1-isoquinolinyl]-1-p-tolylethanone 
• 1141447-82-6 1-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-propan-2-one 
• 1141447-92-8 2-[1,2,3,4-tetrahydro-2-(4-methoxyphenyl)-1-isoquinolinyl]-1-(4-methoxyphenyl)ethanone 
• 1150587-84-0 2,2-difluoro-2-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-1-phenylethanone 

Relevant articles and documents

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

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

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

An oxidant- And catalyst-free electrooxidative cross-coupling approach to 3-tetrahydroisoquinoline substituted coumarins

A direct electrooxidative cross-dehydrogenative-coupling (CDC) reaction betweenN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins has been realized. This protocol provides a green, mild and fast method to construct 3-tetrahydroisoquinoline substituted coumarins in the absence of any catalysts and exogenous oxidants. A variety ofN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins are compatible with this transformation to give the corresponding products in moderate to excellent yields. Moreover, the results of control experiments, cyclic voltammetry experiments, and density functional theory (DFT) calculations indicated that the electrooxidative CDC reaction might involve both radical addition and nucleophilic addition processes.

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.

Visible-light induced Cross-Dehydrogenative-Coupling (CDC) reactions of N-aryl tetrahydroisoquinolines under aerobic conditions

A visible-light induced cross-dehydrogenative-coupling (CDC) reaction of N-aryl tetrahydroisoquinolines was developed under mild aerobic conditions. This protocol proceeded smoothly with a large range of nucleophiles (nitroalkane, dimethyl phosphite, dimethyl malonate, N-methyl indole, TMSCN) under metal-free conditions and an oxygen atmosphere, forming a new C–C bond. Visible-light played a significant acceleration effect in this reaction.

Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: A New Synthetic Approach to α-Monofluoromethyl Tertiary Amines

A cross dehydrogenative coupling reaction of tetrahydroisoquinolines with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide had been developed. CuBr/TBHP was identified as the best catalyst and oxidant. A variety of coupling products were obtained with good t

Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions

Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici

A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence

N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.

Phenazine Radical Cations as Efficient Homogeneous and Heterogeneous Catalysts for the Cross-Dehydrogenative Aza-Henry Reaction

The redox activity of molecular phenazine catalysts has been previously exploited for aerobic oxidative amine homo- and cross-coupling reactions. In this contribution, we have extended the reaction scope of this novel type of organocatalyst and used them in the cross-dehydrogenative aza-Henry coupling of isoquinolines with nitromethane under aerobic conditions. Additionally, we have designed and prepared a novel porous organic polymer by cross-linking of tetrakis(4-bromophenyl)silane and dihydrophenazine through Pd-catalyzed Buchwald-Hartwig cross-coupling. This new type of heterogeneous catalyst, apart from being robust and easily reusable, also showed outstanding catalytic activities and improved selectivity compared to its molecular counterpart. A plausible reaction mechanism was proposed based on spectroscopic and kinetic measurements.