406923-64-6

Basic information

• Product Name: Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro- (9CI)
• Synonyms: Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro- (9CI);Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro-
• CAS NO: 406923-64-6
• Molecular Formula: C9H10FN
• Molecular Weight: 151.1808032
• Product Categories: HALIDE
• Mol File: 406923-64-6.mol

Chemical Properties

• Boiling Point: 234.9 °C at 760 mmHg
• Flash Point: 95.9 °C
• Appearance: /
• Density: 1.107 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro- (9CI)(406923-64-6)
• EPA Substance Registry System: Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro- (9CI)(406923-64-6)

Safety Data

• Hazardous Substances Data: 406923-64-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro(9CI) is used as a key intermediate in the synthesis of various pharmaceuticals, particularly those targeting neurological and mental health disorders. Its unique structure and properties make it a promising candidate for the development of novel therapeutic agents.
Used in Neuroscience Applications:
In the field of neuroscience, Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro(9CI) is used as a research tool to study the mechanisms of neurodegenerative diseases and mental health conditions. Its potential pharmacological properties allow researchers to explore its effects on neurotransmission and neuronal function, contributing to the development of new treatments for these disorders.
Used in Drug Design and Optimization:
The fluorinated structure of Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro(9CI) provides unique opportunities for the design and optimization of new drug candidates. Its incorporation into drug molecules can potentially improve their pharmacokinetic and pharmacodynamic profiles, leading to more effective and safer therapeutic agents.
Used in Medicinal Chemistry:
Isoquinoline, 5-fluoro-1,2,3,4-tetrahydro(9CI) is employed in medicinal chemistry as a building block for the synthesis of bioactive compounds. Its versatile chemical properties enable the development of a wide range of pharmaceuticals with diverse therapeutic applications.

Upstream product

• 52721-69-4 [2-(2-fluorophenyl)ethyl]amine 
• 230301-83-4 5-fluoro-3,4-dihydro-2H-isoquinolin-1-one 
• 1438253-33-8 1-bromo-3-fluoro-2-(2-nitroethyl)benzene 
• 123594-07-0 5-amino-3,4-dihydroisoquinoline-2(H)-carboxylic acid benzyl ester ester 
• 123594-06-9 5-Nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester 
• 41959-45-9 5-nitro-1,2,3,4-tetrahydroisoquinoline 
• 123594-08-1 N-(carbobenzyloxy)-5-fluoro-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

NOVEL TETRAHYDROISOQUINOLINES AND TERAHYDRONAPHTHYRIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The present invention provides novel compounds having the general formula (I): wherein R1, R 2, R 3, U, V, W, X and Y are as described herein, compositions including the compounds and methods of using the compounds.

Heterocyclic compound with Wnt signal path inhibitory activity and application thereof

The invention provides a heterocyclic compound with Wnt signal path inhibitory activity. The heterocyclic compound and chemically acceptable salt, isotope, isomer and a crystal structure thereof are provided with a structure shown as the general formula I (see the formula in the description). The invention further provides application of the heterocyclic compound with the Wnt signal path inhibitory activity. The heterocyclic compound with the Wnt signal path inhibitory activity serves as effective antagonist of a Wnt signal path, and can be used for treating or preventing diseases caused by abnormity of the Wnt signal path.

Affinity of 2-(tetrahydroisoquinolin-2-methyl)- and 2-(isoindolin-2-ylmethyl)imidazolines for α-adrenoceptors. Differential affinity of imidazolines for the [3H]idazoxan-labeled α2-adrenoceptor vs the [3H]yohimbine-labeled site

A series of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines were prepared and tested for α1- and α2-adrenoceptor affinity with radioligand binding. Several compounds, 5-fluoro- (5h), 5-chloro- (5j), 5,8-dimethoxy- (5r), and 5,8-dimethoxy-1-methyl- (5s) 2-(tetrahydroisoquinolin-2-ylmethyl)imidazoline, were found to be selective α2-adrenoceptor ligands on the basis of displacement of [3H]yohimbine from rat cerebral cortical membranes. One compound, 2-[(8-chloro tetrahydroisoquinolin-2-yl)methyl]imidazoline (5m), showed a 36-fold difference in affinity for the [3H]idazoxan-labeled α2-adrenoceptor relative to the [3H]yohimbine-labeled site, which may be evidence for α2-adrenoceptor subtypes.