6529-53-9

Usage

Chemical Properties

Pale yellow oil

InChI:InChI=1/C8H17ClO/c1-3-8(4-2)7-10-6-5-9/h8H,3-7H2,1-2H3

Upstream product

• 75-21-8 oxirane 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 6948-71-6 toluene-4-sulfonic acid 2-(4-chloro-phenyl)-ethyl ester 
• 106-39-8 bromochlorobenzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 141666-91-3 N-[2-(4-chlorophenyl)ethyl]-4-methylbenzenesulfonamide 
• 156-41-2 4-chlorophenylethylamine 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 90867-09-7 4-Chloro-α-ethylbenzenium ion 
• 146404-41-3 C₁₅H₁₇ClN₂O₂S 
• 80019-71-2 methanesulfonic acid-2-(4-chlorophenyl)ethyl ester 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 

Downstream Products

• 101259-37-4 (4-chlorophenethyl)(methyl)sulfane 
• 1073-67-2 4-vinylbenzyl chloride 
• 119364-84-0 (R)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 119298-82-7 (S)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 1028259-01-9 4-[2-(3-Chloro-phenyl)-ethyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 
• 76653-12-8 sodium 4-chloro-β-phenethylsulfonate 
• 42829-08-3 5-(4-chlorophenyl)pentan-2-one 
• 104536-33-6 2-<3-(4-chlorophenyl)propyl>-1-azabicyclo<2.2.2>octan-3-one 
• 64261-05-8 ethyl 4-[2-(4-chlorophenyl)ethylamino]benzoate 
• 66246-26-2 2,4-Bis-(4-chloro-phenyl)-butyronitrile 
• 57186-64-8 1-chloro-4-(2-iodoethyl)-benzene 
• 92294-86-5 ethyl 2-[(4-chlorophenyl)ethyl]-3-oxobutanoate 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 90867-09-7 4-Chloro-α-ethylbenzenium ion 

Relevant academic research and scientific papers

Preparation method of lorcaserin intermediate

The invention relates to a preparation method of a lorcaserin intermediate 1-[2-(4-chlorphenyl)-ethylamino]-2-propanol, which specifically comprises the following steps: carrying out bromination reaction on p-chlorophenethyl alcohol serving as a starting material to obtain 4-chlorphenyl ethyl bromide, and condensing with isopropanolamine to obtain a target product. Hydrobromic acid is used as a bromination reagent, potassium carbonate is used as a condensation reaction acid-binding agent, potassium iodide is used as a condensation reaction catalyst, the yield of the technological process is high, three wastes are few, the cost is low, the operation is simple, the safety is good, and industrial production requirements are met.

Cascade bio-hydroxylation and dehalogenation for one-pot enantioselective synthesis of optically active β-halohydrins from halohydrocarbons

A stereoselective hydroxylation and enantioselective dehalogenation cascade reaction was developed for the synthesis of optically active β-haloalcohols from halohydrocarbons. This cascade system employed P450 and halohydrin dehalogenase as two compatible biocatalysts, allowing a straightforward, greener and efficient access to β-halohydrins with excellent enantioselectivities (98-99%).

Preparation method for hemihydrate lorcaserin hydrochloride

The invention discloses a preparation method for hemihydrate lorcaserin hydrochloride. The preparation method comprises the following steps: (1) making a compound shown as a formula III react with ammonia to obtain a compound shown as a formula II; (2) under the protection of nitrogen gas, dissolving the compound shown as the formula II in an organic solvent, adding a hydrogen chloride solution of which the solvent is the organic solvent to salify, and adding water and cyclohexane to form a hemihydrate in order to obtain the compound shown as a formula I, wherein the organic solvent is isopropanol or 1,4-dioxane. In the preparation method disclosed by the invention, ammonium hydroxide substitutes for potassium carbonate in the prior art, so that unqualified ignition residues of a finial product caused by potassium chloride generated after salt removal can be avoided; an isopropoxide hydrochloride solution substitutes for the conventional hydrogen chloride gas, so that other impurities can be prevented from being introduced in a preparation process under the improper control of dosage and rate of the gas.

Picolinic acids as β-exosite inhibitors of botulinum neurotoxin A light chain

In developing small-molecule inhibitors of botulinum neurotoxin serotype A light chain (BoNT/A LC), substituted picolinic acids were identified. Extensive investigation into the SAR of the picolinic acid scaffold revealed 5-(1-butyl-4-chloro-1H-indol-2-yl)picolinic acid (CBIP), which possessed low micromolar activity against BoNT/A. Kinetic and docking studies demonstrated binding of CBIP to the β-exosite: a largely unexplored site on the LC that holds therapeutic relevance for botulism treatment.

Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

To improve access to a key synthetic intermediate we targeted a direct hydrobromination-Negishi route. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed. Re-examination of early reports revealed that selective Markovnikov addition, often simply termed "normal" addition, is not always observed with HBr unless air is excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol.

Construction of chiral 2-substituted octahydroindoles from cyclic ketones and nitroolefins bearing only one α-substituent

A dual catalytic system has been developed following the screening of a series of chiral primary amine catalysts and chiral phosphoric acid catalysts for the Michael addition of cyclic ketones to nitroolefins bearing only one α-substituent. The resulting γ-nitro ketones, which contain a substituent on the carbon connected to the nitro group, were formed in excellent yields (>80%) with high levels of stereoselectivity (up to 94:6 dr and 98% ee) when the reaction was performed in benzene at 0 °C with 10 mol% of the optimal amine/phosphoric acid combination (1:1) as a catalyst. Subsequent reduction of the nitro group followed by intramolecular reductive amination could afford optically active cis-octahydroindole analogues bearing a non-functional substituent at their 2-position.

The preparation of 3-substituted-1,5-dibromo-pentanes as precursors to heteracyclohexanes

The methodology to prepare 3-substituted 1,5-dibromopentanes I and their immediate precursors, which include 3-substituted 1,5-pentanediols VII or 4-substituted tetrahydropyrans VIII, is surveyed. Such dibromides I are important intermediates in the preparation of liquid crystalline derivatives containing 6-membered heterocyclic rings. Four dibromides 1a-1d containing simple alkyl and more complex fragments at the 3-position were prepared. 3-Propyl- and 3-pentyl-pentane-1,5-diol (2a,b) were prepared starting from either glutaconate or malonate diesters, while tetrahydropyrans 3c and 3d were obtained from tetrahydro-4H-pyran-4-one. The advantages and disadvantages of each route are discussed. Dibromides 1c and 1d were used to prepare sulfonium zwitterions 11c and 11d.

Processes for the Preparation of 8-Chloro-1-Methyl-2,3,4,5-Tetrahydro-1H-3-Benzazepine and Intermediates Related Thereto

The present invention provides processes, methods and intermediates for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, salts, hydrates and crystal forms thereof which are useful as serotonin (5-HT) receptor agonists for the treatment of, for example, central nervous system disorders such as obesity.

PROCESSES FOR THE PREPARATION OF INTERMEDIATES RELATED TO THE 5-HT2C AGONIST (R)-8-CHLORO-1-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE

The present invention provides processes and intermediates useful in the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, a serotonin (5-HT) receptor agonist that is useful in the treatment or prophylaxis of, for example, central nervous system disorders, such as obesity.

Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)

We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17α-hydroxylase/17,20-lyase (P45017α), that is, 17α-hydroxylase (17α-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 μM against 17α-OHase and IC50 = 0.33 μM against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 μM against 17α-OHase and IC50 = 1.66 μM against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency.