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Usage

Uses

Used in Pharmaceutical and Agrochemical Production:
2-Chloro-1-formyl-1-cyclohexene is utilized as a key building block in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Organic Synthesis:
2-Chloro-1-formyl-1-cyclohexene serves as a reagent in organic reactions, particularly in the synthesis of heterocyclic compounds, which are important in the creation of a wide range of chemical products.
Used in Research and Development:
2-Chloro-1-formyl-1-cyclohexene is under investigation for its potential therapeutic applications, especially as an inhibitor of monoamine oxidase A (MAO-A), which could lead to treatments for neurological and mood disorders.
Used in Chemical Research:
Due to its unique chemical properties, 2-Chloro-1-formyl-1-cyclohexene is also used in chemical research to explore new synthetic pathways and understand the reactivity of similar compounds.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 108-94-1 cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 4065-81-0 cyclohexen-1-ol 
• 79-01-6 Trichloroethylene 
• 50-00-0 formaldehyd 
• 822-87-7 2-Chlorocyclohexanone 

Downstream Products

• 5632-33-7 5,6,7,8-tetrahydroquinazoline 
• 55338-89-1 [(2-Chloro-cyclohex-1-enyl)-hydroxy-methyl]-phosphonic acid dimethyl ester 
• 81023-52-1 C₁₉H₂₀N₂ 
• 55338-78-8 [(2-Chloro-cyclohex-1-enyl)-hydroxy-methyl]-phosphonic acid diethyl ester 
• 113684-03-0 1-Chlor-2-(1'-hydroxy-ethyl)-cyclohexen 
• 120504-82-7 1-(2-Chloro-cyclohex-1-enyl)-propan-1-ol 
• 52776-44-0 (2-Chloro-cyclohex-1-enyl)-phenyl-methanol 
• 65880-18-4 4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester 
• 113684-01-8 1-Chlor-2-(1'-chlor-ethyl)-cyclohexen 
• 120504-89-4 1-Chloro-2-(1-chloro-propyl)-cyclohexene 

Relevant academic research and scientific papers

Vilsmeier Formylation of O-Silylated Enolates of Carboxylic Esters. A New Method for the Synthesis of α-Formylcarboxylic Esters

The Vilsmeier formylation of ketene O-alkyl O'-silyl acetals (O-silylated enolates of carboxylic esters) provides α-formylcarboxylic esters in moderate yields.

A facile and convenient synthesis of (±)-biotin via MgCl2/Et3N-mediated C-C coupling and Mitsunobu reaction

A synthesis of (±)-biotin is described starting from simple starting materials viz. cyclohexanone and amino malonic acid ester. The key steps involved are MgCl2/Et3N coupling of amino malonic acid ester derivative and acid chloride,

β-Chloroaldehydes from Trapping Zirconium Enolates Produced in Asymmetric 1,4-Additions

Zirconium enolates, derived from copper-catalyzed asymmetric conjugate additions, are trapped with the Vilsmeier-Haack reagent. Asymmetric additions generate quaternary carbon centers with high enantioselectivity (generally ?90% ee), and the enolates are converted to unsaturated β-chloroaldehydes (41-57% yields). The reaction tolerates changes to the nucleophile, can be used to form five-, six-, or seven-membered ring products, and is scalable to 5 mmol, and the products are readily elaborated by condensation, cross coupling, and addition reactions.

A General Strategy for Macrotheranostic Prodrug Activation: Synergy between the Acidic Tumor Microenvironment and Bioorthogonal Chemistry

Prodrugs activated by endogenous stimuli face the problem of tumor heterogeneity. Bioorthogonal prodrug activation that utilizes an exogenous click reaction has the potential to solve this problem, but most of the strategies currently used rely on the pre

Cyclization of β-Chlorovinyl Thiohydrazones into Pyridazines: A Mechanistic Study

Extensive experimental and theoretical investigations on the isomerization and heterocyclizations of β-chlorovinyl thiohydrazones derived from oxamic acid thiohydrazides and β-chlorovinyl aldehydes were performed to elucidate the reaction mechanism of pyr

Two-Step Synthesis of 3,4-Dihydropyrrolopyrazinones from Ketones and Piperazin-2-ones

An expedient two-step synthesis of 3,4-dihydropyrrolopyrazinones has been achieved via a Vilsmeier-Haack reaction of ketones, followed by an annulation of the corresponding chloroaldehydes with commercially available piperazin-2-ones. A variety of cyclic and acyclic ketones and piperazin-2-ones participated in this two-step chemistry, affording the desired 3,4-dihydropyrrolopyrazinones in up to 78% yield.

Efficient synthesis of 4- And 5-substituted 2-aminopyrimidines by coupling of β-Chlorovinyl Aldehydes and Guanidines

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involving the Vilsmeier-Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional-group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

Synthesis, structure and reactivity of β-chalcocyclohexenals: Dichalcogenides and chalcogenides

The present work describes the synthesis and characterization of a series of organochalcogen compounds derived from β-chlorocyclohexenal (27a)/β-bromocyclohexenal (27b) which are stabilized by E...O (E = S, Se, Te) intramolecular secondary bonding interaction (IM-SBI). Di-(2-formylcyclohex-1-ene)sulfide (21) was prepared by treating 27b with disodium sulfide. Di-(2-formylcyclohex-1-ene)diselenide (28) was obtained by reacting 27a with disodium diselenide. The reaction always produced a mixture of di-(2-formylcyclohex-1-ene)diselenide (28) and di-(2-formylcyclohex-1-ene)selenide (29). Attempts to synthesize di-(2-formylcyclohex-1-ene)ditelluride 30 by the reaction of 27b with disodium ditelluride afforded a mixture of monotellurides; 3,4,5,6,7,8-hexahydro-2H-9-telluraanthracene-1-carbaldehyde (26), di-(2-formylcyclohex-1-ene)telluride (22) and 9-hydroxy-2,3,5,6,7,8,9,9a-octahydro-1H-telluroxanthene-4-carbaldehyde (31). Reactions of 28 with halogenating reagents afforded the corresponding organylselenenyl halides; selenenyl chloride 35, selenenyl bromide 36 and selenenyl iodide 37. Tellurides 26 and 22 were used as ligands for metal complexation reactions.

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.