30005-58-4

Basic information

• Product Name: 4-(4-Chlorophenyl)1,2,3,6-
• Synonyms: 4-(4-Chlorophenyl)1,2,3,6-;4-CHLOROPHENYL-1,2,3,6-TETRAHYDROPYRIDINE
• CAS NO: 30005-58-4
• Molecular Formula: C₁₁H₁₂ClN
• Molecular Weight: 193.6727
• Mol File: 30005-58-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 296.5°Cat760mmHg
• Flash Point: 133.1°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 0.00143mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 4-(4-Chlorophenyl)1,2,3,6-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Chlorophenyl)1,2,3,6-(30005-58-4)
• EPA Substance Registry System: 4-(4-Chlorophenyl)1,2,3,6-(30005-58-4)

Safety Data

• Hazardous Substances Data: 30005-58-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12ClN/c12-11-3-1-9(2-4-11)10-5-7-13-8-6-10/h1-5,13H,6-8H2

Upstream product

• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 138647-50-4 4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 235109-63-4 4-(4-chloro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 51304-61-1 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride 
• 50-00-0 formaldehyd 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 84501-69-9 4-bromo-4-(4-chloro-phenyl)-piperidine; hydrobromide 
• 153680-73-0 {2-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-carbamic acid ethyl ester 
• 72850-42-1 4-(4-chlorophenyl)-1-<(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)ethyl>-1,2,3,6-tetrahydropyridine 
• 139652-34-9 6-[6-(4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridyl)hexoxy]-2-phenyl-4H-1-benzopyran-4-one 
• 94427-27-7 1-(methoxycarbonyl)-4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine 
• 178265-89-9 4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 5957-96-0 4-(4-chlorophenyl)pyridine 
• 26905-02-2 4-(4-chlorophenyl)piperidine 

Relevant articles and documents

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D2 Receptor

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side effects (EPSs) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D2 receptor (D2R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D2R, whereas clozapine exhibits relatively slow association/fast dissociation. Recently, we have provided evidence that slow dissociation from the D2R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side effects independent of its D2R action. Our results suggest an optimal kinetic profile for D2R antagonist APDs that avoids EPS. To begin exploring this hypothesis, we conducted a structure-kinetic relationship study of haloperidol and revealed that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles.

Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines

A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ 19F NMR.

Design, synthesis, and evaluation of novel aryl-tetrahydropyridine PPARα/γ dual agonists

Aryl-tetrahydropyridine derivatives were prepared and their PPARα/γ dual agonistic activities were evaluated. Among them, compound (S)-5b was identified as a potent PPARα/γ dual agonist with an EC50 of 1.73 and 0.64 μM in hPPARα and γ, respectively. In diabetic (db/db) mice, compound (S)-5b showed good glucose lowering efficacy and favorable pharmacokinetic properties.