167081-25-6

Basic information

• Product Name: TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE
• Synonyms: TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE;cis-N-Boc-4-amino-cyclohexanol;cis-(4-Hydroxycyclohexyl)carbamic acid tert-butyl ester;tert-Butyl cis-4-hydroxycyclohexanecarbaMate;CarbaMicacid, (4-hydroxycyclohexyl)-, 1,1-diMethylethyl ester, cis-;tert-butyl N-(4-hydroxycyclohexyl)carbaMate;tert-butyl N-[(1s,4s)-4- hydroxycyclohexyl]carbaMate;cis-4-(tert-ButoxycarbonylaMino)cyclohexanol
• CAS NO: 167081-25-6
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• Mol File: 167081-25-6.mol

Chemical Properties

• Melting Point: 95 °C
• Boiling Point: 337.714 °C at 760 mmHg
• Flash Point: 158.044 °C
• Appearance: /
• Density: 1.066 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 12.36±0.40(Predicted)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE(167081-25-6)
• EPA Substance Registry System: TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE(167081-25-6)

Safety Data

• Hazardous Substances Data: 167081-25-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL CIS-4-HYDROXYCYCLOHEXYLCARBAMATE is used as a reagent for the synthesis of pyrazolo[3,4-d]pyrimidines, compounds that have potential anti-inflammatory and antitumor properties. This makes it a valuable component in the development of new drugs for the treatment of inflammation and cancer.

Upstream product

• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123-30-8 4-amino-phenol 
• 100-02-7 4-nitro-phenol 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 56239-26-0 (1s,4s)-4-aminocyclohexan-1-ol hydrochloride 
• 6850-65-3 cis-4-aminocyclohexanol 
• 111300-06-2 trans-tert-butyl 4-hydroxycyclohexylcarbamate 
• 847416-31-3 cis-4-((tert-butoxycarbonyl)amino)cyclohexyl 4-nitrobenzoate 
• 27489-62-9 trans-4-hydroxycyclohexylamine 

Downstream Products

• 1007306-61-7 (1S,4S)-4-((tert-butoxycarbonyl)amino)-cyclohexyl methanesulfonate 

Relevant articles and documents

Compounds and methods of use

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein X1, X2, X3, X4, Y, A, L1, L2, R1, R2, R5, m and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

NOVEL COMPOUNDS AND THEIR USE

The present invention provides compounds of the general formula (I) or a pharmaceutically acceptable prodrugs, salts and/or solvates thereof, wherein LHS is selected from the group consisting of LHSa and LHSb And wherein, the asterisk (*) marks the point of attachment; These compounds exhibit antibacterial activity against Gram-negative and Gram-positive bacteria, especially S. aureus, E. coli, K. pneumoniae and A. baumannii. Pharmaceutical compositions containing these compounds, therapeutic uses thereof and methods for manufacturing the same are also provided.

Palladium-Catalyzed C-O Cross-Coupling as a Replacement for a Mitsunobu Reaction in the Development of an Androgen Receptor Antagonist

A scalable and efficient synthesis of N-{trans-4-[(8-cyanoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide (BAY 1161116), an androgen receptor antagonist, is reported. The original synthesis included a low-yielding Mitsunobu reaction and employed cis-aminocyclohexanol, which is accessible only via a troublesome synthesis, as a key building block. The novel synthetic pathway starts from readily available trans-aminocyclohexanol and features a palladium-catalyzed etherification reaction in place of the Mitsunobu reaction as the key step. This four-step synthesis can be performed reliably on a multikilogram scale, and purification of all intermediates as well as the final product can be achieved by simple extraction and crystallization procedures.

Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives

A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.

Catalytic Transfer Hydrogenation of Arenes and Heteroarenes

Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds. In this context, we have developed a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas.

POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

SUBSTITUTED BENZAMIDES AND THEIR USES

Provided herein are Substituted Benzamides, compositions, and method of their manufacture and use.

NOVEL COMPOUNDS AND THEIR USE IN THERAPY

The invention provides compounds which inhibit N-myristoyltransferase and are selective for protozoal N-myristoyltransferase and, consequently suitable to treat microbial infections, including viral and fungal infections, and protozoan infections such as malaria, leishmaniasis and sleeping sickness.

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.

ANTITHROMBOTIC ETHERS

This application relates to a compound of formula I (or a prodrug thereof or a pharmaceutically acceptable salt of the compound or prodrug thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa and/or thrombin, as well as a process for its preparation and intermediates therefor (I).