6140-64-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylcyclohexanecarboxaldehyde is used as a key intermediate in the synthesis of Indazole derivatives, which are known as IDO (Indoleamine 2,3-dioxygenase) and TDO (Tryptophan 2,3-dioxygenase) modulators. These modulators have potential applications in the treatment of various diseases, including cancer, neurodegenerative disorders, and inflammatory conditions, by targeting the IDO and TDO enzymes involved in the kynurenine pathway.
In the preparation of Indazole derivatives, 1-Methylcyclohexanecarboxaldehyde serves as a valuable building block, enabling the development of novel and effective therapeutic agents. Its unique structure and reactivity make it an essential component in the synthesis of these biologically active compounds, contributing to advancements in medicine and healthcare.

Synthesis Reference(s)

Journal of the American Chemical Society, 114, p. 4422, 1992 DOI: 10.1021/ja00037a070

Upstream product

• 1453-25-4 1-methylcycloheptene 
• 1123-25-7 1-methyl-1-cyclohexanecarboxylic acid 
• 30451-98-0 1-Methoxyspiro<2.5>octan 
• 931-96-4 1-methyl-3-cyclohexene-1-carboxaldehyde 
• 2890-61-1 1-methyl-1-cyclohexancarboxylic acid chloride 
• 2658-60-8 1,1-bis(hydroxymethyl)cyclohexane 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 14064-13-2 (1-methylcyclohexyl)methanol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 74-88-4 methyl iodide 
• 55089-30-0 2-(1-methyl-cyclohexyl)-4,5-dihydro-thiazole 
• 111-24-0 1,5-dibromo-pentane 
• 825-04-7 methyl 1-methylcyclohexanecarboxylate 

Downstream Products

• 62257-88-9 N,N-dimethyl-1-(1-methylcyclohexyl)methanamine 
• 590-66-9 1,1-dimethylcyclohexane 
• 103168-39-4 1-Methyl-1-diaminomethyl-N.N'-bis-<1-methyl-cyclohexylmethylen>-cyclohexan 
• 21623-78-9 1-methyl-1-vinylcyclohexane 
• 2955-96-6 Methyl-chloracetoxyacetat 
• 153791-49-2 Methyl <(1-methyl-1-cyclohexanecarbonyl)acetoxy>acetate 
• 161139-35-1 methyl N-(4-methoxybenzyl)-N-<3-(1-methylcyclohexyl)-3-oxopropanoyl>glycinate 
• 1123-25-7 1-methyl-1-cyclohexanecarboxylic acid 
• 869997-15-9 5-(2-adamantan-1-yl-ethyl)-2-(1-methyl-cyclohexyl)-1H-imidazole-4-carboxylic acid ethyl ester 
• 103096-65-7 N-(1-Methyl-cyclohexylmethylen)-(1-methyl-cyclohexylmethyl)-amin 
• 923591-39-3 (2R)-{[(1R)-2-hydroxy-1-phenylethyl]amino}(1-methylcyclohexyl)acetonitrile 
• 1227718-79-7 (Z)-3-(1-methylcyclohexyl)acrylonitrile 
• 1262639-74-6 2-(methyl-((1-methylcyclohexyl)methyl)amino)ethanenitrile 
• 1632260-97-9 (R)-4-hydroxy-4-(1-methylcyclohexyl)-2-butanone 

Relevant academic research and scientific papers

Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents

A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fa

Preparation of isoquinazolines: Via metal-free [4 + 2] cycloaddition of ynamides with nitriles

TfOH-mediated [4 + 2] cycloaddition of ynamides with nitriles to construct 1,2-dihydroquinazolines is realized by a direct reaction in moderate to excellent yields (up to 93%) in a stereospecific manner. A rapid and efficient strategy has been employed for the syntheses of alkyl-substituted 1,2-dihydroquinazoline derivatives, and it exhibits good functional group tolerance, has a short reaction time, shows excellent diastereoselectivity, and is a simple and high-yielding reaction.

Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates

Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.

COMPOUNDS AND RELATED METHODS OF USE

Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

Tropylium ion mediated α-cyanation of amines

Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the α-cyanation procedure, including a gram scale synthesis of 17β-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.

Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors

A practical and efficient route toward synthesis of amino acid derivatives containing β-quaternary center has been developed using diastereoselective Strecker reaction. The method was employed for preparation of >100 g of β-methylcyclohexyl glycine deriva

HCV NS3 protease inhibitors

The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

The tris(trimethylsilyl)silane/thiol reducing system: A tool for measuring rate constants for reactions of carbon-centered radicals with thiols

An extension of the well-known 'free-radical-clock' methodology is described that allows one to determine the rate constants of carbon-centered radicals with a variety of thiols by using the tris(trime-thylsilyl)silane/thiol couple as a reducing system. A

NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.