265108-36-9

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxaldehyde, 4,4-difluoro(9CI) is used as a key intermediate in the synthesis of heteroaryl acid derivatives. These derivatives are essential in the development of novel pharmaceutical compounds, particularly those targeting oxalate-related diseases. The unique structural features of Cyclohexanecarboxaldehyde, 4,4-difluoro- (9CI) allow for the creation of new molecules with potential therapeutic benefits.
Used in Chemical Synthesis:
In the field of chemical synthesis, Cyclohexanecarboxaldehyde, 4,4-difluoro(9CI) serves as a valuable building block for the development of various organic compounds. Its fluorinated nature and reactive aldehyde group make it a versatile starting material for the synthesis of a wide range of molecules with diverse applications, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Research and Development:
Due to its unique structure and reactivity, Cyclohexanecarboxaldehyde, 4,4-difluoro(9CI) is also utilized in research and development laboratories. It can be employed as a model compound to study the effects of fluorination on the properties and reactivity of cyclohexane derivatives. Additionally, it can be used to explore new reaction pathways and develop innovative synthetic methods for the preparation of complex organic molecules.

Upstream product

• 394-02-5 5-fluoro-2-nitrobenzoyl chloride 
• 178312-48-6 (4,4-difluorocyclohexyl)methanol 
• 178312-47-5 ethyl 4,4-difluorocyclohexane-1-carboxylate 
• 122665-97-8 4,4-difluorocyclohexanecarboxylic acid 
• 3618-04-0 4-hydroxycyclohexyl carboxylic acid ethyl ester 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 121629-14-9 methyl 4,4-difluorocyclohexane-1-carboxylate 
• 917383-03-0 4,4-difluoro-N-methoxy-N-methylcyclohexane-1-carboxamide 

Downstream Products

• 1156469-52-1 C₉H₁₄F₂O 
• 1427058-51-2 tert-butyl N-{1-[(4,4-difluorocyclohexyl)methyl]piperidin-4-yl}carbamate 

Relevant academic research and scientific papers

Structure-Guided Design of Potent Inhibitors of SARS-CoV-2 3CL Protease: Structural, Biochemical, and Cell-Based Studies

The COVID-19 pandemic is having a major impact on public health worldwide, and there is an urgent need for the creation of an armamentarium of effective therapeutics, including vaccines, biologics, and small-molecule therapeutics, to combat SARS-CoV-2 and emerging variants. Inspection of the virus life cycle reveals multiple viral- and host-based choke points that can be exploited to combat the virus. SARS-CoV-2 3C-like protease (3CLpro), an enzyme essential for viral replication, is an attractive target for therapeutic intervention, and the design of inhibitors of the protease may lead to the emergence of effective SARS-CoV-2-specific antivirals. We describe herein the results of our studies related to the application of X-ray crystallography, the Thorpe–Ingold effect, deuteration, and stereochemistry in the design of highly potent and nontoxic inhibitors of SARS-CoV-2 3CLpro.

THERAPEUTIC COMPOUNDS AND METHODS OF USE

The invention relates to compounds and methods of using said compounds, as well as pharmaceutical compositions containing such compounds, for treating diseases and conditions mediated by TEAD, such as cancer.

COMPOUNDS AND METHODS FOR TREATING OXALATE-RELATED DISEASES

Disclosed herein are compounds and compositions for modulating glycolate oxidase, useful for treating oxalate-related diseases, such as hyperoxaluria, where modulating glycolate oxidase is expected to be therapeutic to a patent in need thereof. Methods of modulating glycolate oxidase activity in a human or animal subject are also provided.

Methylene C(sp3)-H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand

A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.

CRYSTAL OF TRICYCLIC COMPOUND

The present application relates to a crystal of a tricyclic compound, in particular to a crystal of (S)-8-(4,4-difluorocyclohexyl)-8H-thieno[3,4]pyrrolo[1,5-a]imidazole, a preparation method therefor, a crystal composition and a pharmaceutical composition thereof and the use thereof. The X-ray powder diffraction spectrum of the crystal of the compound of formula I in the present application, represented by a 2θ value, has a diffraction peak at about 11.49°, 15.05°, 20.14°, 21.53° or 21.79°. The crystal of the compound of formula I in the present application has excellent physical properties, high safety and metabolic stability, and has a good inhibitory effect on IDO and a high medicinal value.

CARBOXAMIDE AND SULFONAMIDE DERIVATIVES USEFUL AS TEAD MODULATORS

The invention is concerned with the compounds of formula (I) and formula (II): and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of using the compounds of formula (I) and formula (II) as well as pharmaceutical compositions containing such compounds. The compounds are useful in treating diseases and conditions mediated by TEAD, such as cancer.

Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.

TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR

Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.

Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy

We designed and synthesized perhexiline analogues that have the same therapeutic profile as the parent cardiovascular drug but lacking its metabolic liability associated with CYP2D6 metabolism. Cycloalkyl perhexiline analogues 6a-j were found to be unsuitable for further development, as they retained a pharmacokinetic profile very similar to that shown by the parent compound. Multistep synthesis of perhexiline analogues incorporating fluorine atoms onto the cyclohexyl ring(s) provided a range of different fluoroperhexiline analogues. Of these, analogues 50 (4,4-gem-difluoro) and 62 (4,4,4′,4′-tetrafluoro) were highly stable and showed greatly reduced susceptibility to CYP2D6-mediated metabolism. In vitro efficacy studies demonstrated that a number of derivatives retained acceptable potency against CPT-1. Having the best balance of properties, 50 was selected for further evaluation. Like perhexiline, it was shown to be selectively concentrated in the myocardium and, using the Langendorff model, to be effective in improving both cardiac contractility and relaxation when challenged with high fat buffer.

Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies

4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate (3b) is a potent, selective and systemically active inhibitor of intracellular NAAA activity, which produces profound anti-inflammatory effects in animal models. In the present work, we describe structure-activity relationship (SAR) studies on 3-aminoazetidin-2-one derivatives, which have led to the identification of 3b, and expand these studies to elucidate the principal structural and stereochemical features needed to achieve effective NAAA inhibition. Investigations on the influence of the substitution at the β-position of the 2-oxo-3-azetidinyl ring as well as on the effect of size and shape of the carbamic acid ester side chain led to the discovery of 3ak, a novel inhibitor of human NAAA that shows an improved physicochemical and drug-like profile relative to 3b. This favourable profile, along with the structural diversity of the carbamic acid chain of 3b, identify this compound as a promising new tool to investigate the potential of NAAA inhibitors as therapeutic agents for the treatment of pain and inflammation.