75877-66-6

Usage

Uses

Used in Pharmaceutical Industry:
cis-Ethyl 4-hydroxycyclohexanecarboxylate is used as an intermediate in the synthesis of various drugs, contributing to the development of new medicinal compounds due to its ability to participate in a range of synthetic processes.
Used in Agrochemical Industry:
In the agrochemical sector, cis-Ethyl 4-hydroxycyclohexanecarboxylate serves as a key building block in the production of agrochemicals, enhancing the effectiveness of these products through its versatile chemical properties.
Used in Flavor and Fragrance Industry:
cis-Ethyl 4-hydroxycyclohexanecarboxylate is employed as a key ingredient in the creation of certain scents and flavors, leveraging its unique chemical structure to contribute to the complexity and appeal of fragrances and flavor profiles.

Upstream product

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 64-17-5 ethanol 
• 3685-22-1 4-hydroxycyclohexanecarboxylic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 3685-26-5 trans-4-hydroxycyclohexanecarboxylic acid 
• 123-91-1 1,4-dioxane 
• 3685-26-5 cis-4-hydroxycyclohexanecarboxylic acid 

Downstream Products

• 53287-45-9 4-chloro-1-cyclohexanecarboxylic acid chloride 
• 15580-00-4 1-Phenylsulfon-2-oxo-2-(4-hydroxy-cyclohexyl)ethan 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 1221724-30-6 4-hydroxycyclohexane-1-carboxamide 
• 676560-15-9 Ethyl (cis/trans)-4-<(tert-butyldimethylsilyl)oxy>cyclohexanecarboxylate 
• 17328-67-5 4-(2-hydroxypropan-2-yl)cyclohexanone 
• 223699-80-7 cis-pentamethylbenzyl 4-hydroxycyclohexanecarboxylate 
• 3685-22-1 4-hydroxycyclohexanecarboxylic acid 
• 923-42-2 butane-1,2,4-tricarboxylic acid 
• 888970-51-2 4-fluoro-cyclohexanecarboxylic acid pentamethylphenylmethyl ester 
• 223699-83-0 trans-pentamethylbenzyl 4-fluorocyclohexanecarboxylate 
• 952588-97-5 4-(4-ethoxycarbonyl-cyclohexyloxy)-benzoic acid benzyl ester 
• 956122-83-1 ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexanecarboxylate 
• 17419-82-8 cis/trans-4-hydroxy-cyclohexanecarboxylic acid hydrazide 

Relevant academic research and scientific papers

HETEROARYLDIHYDROPYRIMIDINE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS

Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.

A Practical and Stereoselective In Situ NHC-Cobalt Catalytic System for Hydrogenation of Ketones and Aldehydes

Homogeneous catalytic hydrogenation of carbonyl groups is a synthetically useful and widely applied organic transformation. Sustainable chemistry goals require replacing conventional noble transition metal catalysts for hydrogenation by earth-abundant base metals. Herein, we report how a practical in situ catalytic system generated by easily available pincer NHC precursors, CoCl2, and a base enabled efficient and high-yielding hydrogenation of a broad range of ketones and aldehydes (over 50 examples and a maximum turnover number [TON] of 2,610). This is the first example of NHC-Co-catalyzed hydrogenation of C=O bonds using flexible pincer NHC ligands consisting of a N-H substructure. Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized by fine-tuning of the steric bulk of pincer NHC ligands. Additionally, a bis(NHCs)-Co complex was successfully isolated and fully characterized, and it exhibits excellent catalytic activity that equals that of the in-situ-formed catalytic system. Catalytic hydrogenation is a powerful tool for the reduction of organic compounds in both fine and bulk chemical industries. To improve sustainability, more ecofriendly, inexpensive, and earth-abundant base metals should be employed to replace the precious metals that currently dominate the development of hydrogenation catalysts. However, the majority of the base-metal catalysts that have been reported involve expensive, complex, and often air- and moisture-sensitive phosphine ligands, impeding their widespread application. From a mixture of the stable CoCl2, imidazole salts, and a base, our newly developed catalytic system that formed easily in situ enables efficient and stereoselective hydrogenation of C=O bonds. We anticipate that this easily accessible catalytic system will create opportunities for the design of practical base-metal hydrogenation catalysts. A practical in situ catalytic system generated by a mixture of easily available pincer NHC precursors, CoCl2, and a base enabled highly efficient hydrogenation of a broad range of ketones and aldehydes (over 50 examples and up to a turnover number [TON] of 2,610). Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized in high selectivities. Moreover, the preparation of a well-defined bis(NHCs)-Co complex via this pincer NHC ligand consisting of a N-H substructure was successful, and it exhibits equally excellent catalytic activity for the hydrogenation of C=O bonds.

Design, Synthesis, and Biological Evaluation of First-in-Class Dual Acting Histone Deacetylases (HDACs) and Phosphodiesterase 5 (PDE5) Inhibitors for the Treatment of Alzheimer's Disease

Simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylases (HDAC) has recently been validated as a potentially novel therapeutic approach for Alzheimer's disease (AD). To further extend this concept, we designed and synthesized the first chemical series of dual acting PDE5 and HDAC inhibitors, and we validated this systems therapeutics approach. Following the implementation of structure- and knowledge-based approaches, initial hits were designed and were shown to validate our hypothesis of dual in vitro inhibition. Then, an optimization strategy was pursued to obtain a proper tool compound for in vivo testing in AD models. Initial hits were translated into molecules with adequate cellular functional responses (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation in the nanomolar range), an acceptable therapeutic window (>1 log unit), and the ability to cross the blood-brain barrier, leading to the identification of 7 as a candidate for in vivo proof-of-concept testing (Cuadrado-Tejedor, M.; Garcia-Barroso, C.; Sánchez-Arias, J. A.; Rabal, O.; Mederos, S.; Ugarte, A.; Franco, R.; Segura, V.; Perea, G.; Oyarzabal, J.; Garcia-Osta, A. Neuropsychopharmacology 2016, in press, doi: 10.1038/npp.2016.163).

NOVEL COMPOUNDS AS DUAL INHIBITORS OF PHOSPHODIESTERASES AND HISTONE DEACETYLASES

It relates to certain compounds having a polycyclic structure and a hydroxamic acid moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to a process for their preparation, as well as to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases. wherein B1 is a radical selected from the group consisting of formula (A"), formula (B"), formula (C"), and formula (D"):

A biocatalytic/reductive etherification approach to substituted piperidinyl ethers

A synthetically useful protocol has been developed for the preparation of highly functionalized piperidinyl ethers. Biocatalytic reduction of cyclhexanones 7, 10, and 14 allows for the preparation of both cis- and trans diastereomers with an extremely high degree of stereochemical control. Reductive etherification of the corresponding trimethylsilylethers with 1-(benzyloxycarbonyl)-4-piperidinone 17 in the presence of triethylsilane and catalytic TMSO-Tf provides the desired piperidinyl ethers in good to excellent yields. Finally hygrogenolysis of the nitrogen protecting group leads to piperidinyl ethers in near quantitative yields. Application of the methodology to a range of piperidinyl ethers, including the core scaffolds of diphenylpyraline and ebastine, is also described.

IMIDAZOLE DERIVATIVES

Described herein are compounds of formula (I), The compounds of formula I act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.

Fused Bicyclic Kinase Inhibitors

Compounds of Formula I, as shown below and defined herein: pharmaceutically acceptable salts thereof, synthesis, intermediates, formulations, and methods of disease treatment therewith, including treatment of cancers, such as tumors driven at least in part by at least one of RON, MET or ALK. This Abstract is not limiting of the invention.

A scalable synthesis of a 1,7-naphthyridine derivative, a PDE-4 inhibitor

A six-step synthesis of a 4-[8-(3-fluorophenyl)[1,7]naphthyridin-6-yl]- trans-cyclohexanecarboxylic acid with an overall yield of 27% starting from 2-cyano-3-methylpyridine, cyclohexane-1,4-dicarboxylic acid dimethyl ester, and 3-fluorophenylboronic acid is described. The trans stereochemistry in the cyclohexane moiety was achieved through a series of equilibration steps at different stages of the synthesis.

2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY

2,4-Diaminoquinazolines of formula (I) are provided herein and are useful for treating spinal muscular atrophy (SMA).

4-CYCLOALKYLAMINOPYRAZOLO PYRIMIDINE NMDA/NR2B ANTAGONISTS

Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are effective as NMDA/NR2B antagonists useful for treating neurological conditions such as, for example, pain, Parkinson's disease, Alzheimer's disease, epilepsy, depression, anxiety, ischemic brain injury including stroke, and other conditions.