3618-04-0

Basic information

• Product Name: 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER
• Synonyms: 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER;Ethyl trans-4-Hydroxycyclohexanecarboxylate;trans-4-Hydroxycyclohexanecarboxylic Acid Ethyl Ester;trans-Ethyl 4-hydroxycyclohexanecarboxylate;3618-04-0, 17159-80-7, 75877-66-6;3618-04-0, 75877-66-6, 17159-80-7;Ethyl trans-4-hydroxycyclohexane-1-carboxylate
• CAS NO: 3618-04-0
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22
• Mol File: 3618-04-0.mol

Chemical Properties

• Boiling Point: 144°C/12mmHg(lit.)
• Flash Point: 100.193°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.4630 to 1.4670
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.98±0.40(Predicted)
• CAS DataBase Reference: 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER(3618-04-0)
• EPA Substance Registry System: 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER(3618-04-0)

Safety Data

• Hazardous Substances Data: 3618-04-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER is used as a reagent for the discovery of Mer kinase inhibitors. These inhibitors are being investigated for their potential in treating pediatric acute lymphoblastic leukemia, a type of cancer that primarily affects children.
Used in Antiviral Research:
In the field of antiviral research, 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER is utilized in the structural activity relationship study of piperidine-based derivatives. These derivatives are being explored as novel influenza virus inhibitors, with the aim of developing new treatments for influenza infections.
Used in Chemical Synthesis:
4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER can also be employed as an intermediate in the synthesis of various chemical compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable building block in organic chemistry.
Used in Flavor and Fragrance Industry:
Due to its fruity odor, 4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER may find applications in the flavor and fragrance industry, where it can be used to create or enhance the scent of various products, such as perfumes, cosmetics, and food additives.

InChI:InChI=1/C9H16O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h7-8,10H,2-6H2,1H3/t7-,8-

Upstream product

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

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.

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.

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).

THERAPEUTIC AMIDE DERIVATIVES

The present invention relates to compounds of the formula (I): or a pharmaceutically acceptable salt or solvate thereof, wherein: A and B independently represent CH2 or O, with the proviso that A and B are not simultaneously O; Cy represents one of the following Formula (II) optionally substituted by one to three groups selected from hydroxy, halogen, C1-6alkyl, C1-6alkoxy, C1-6 haloalkyl, C1-6alkylamino and amino; R1 and R2 are independently selected from hydroxy, halogen, C1-6alkyl, C1-6alkoxy, C1-6 haloalkyl and C3-8 cycloalkyl; n represents an integer from 0-4; X is hydrogen, hydroxy, halogen or C1-6alkoxy; Y is oxy, thio, a 1-4 membered alkylene, a 2-4 membered alkylene ether, 2-4 membered alkylene thioether or an oxyethyleneoxy group, optionally substituted by 1 to 4 groups independently selected from hydroxy, halogen, C1-6alkyl, C1-6alkoxy and C1-6 haloalkyl; Z is CH or N; and p represents an integer from 0-5 when Z is CH or 0-4 when Z is N; when p represents 2 or more, two of R2s may be taken together with the carbon atoms to which they are attached to form a 5-8 membered cycloalkyl ring to processes for the preparation of, intermediates used in the preparation of, compositions containing such compounds and the uses of such compounds as antagonists of the NMDA NR2B receptor.

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.

Selective reductions with stable indium trihydride reagents

The carbene and tertiary phosphine adducts of indane, [InH3{CN(Mes)C2H2N(Mes)}] and [InH3{P(C6H11)3}] (Mes = 2,4,6-trimethylphenyl), have been used to reduce unsaturated organic functionalities. The success and selectivity of these reductions relative to those carried out with lighter group 13 hydride complexes is discussed. (C) 2000 Elsevier Science Ltd.