73446-71-6

Upstream product

• 1713-33-3 1,2-epoxy-1-methylcyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 1713-33-3 cis-1,2-epoxy-1-methylcyclohexane 
• 75-16-1 methylmagnesium bromide 
• 583-59-5 2-Methylcyclohexanol 

Downstream Products

• 40648-23-5 (±)-6-bromo-1-methylcyclohex-1-ene 
• 40940-64-5 (±)-6-bromo-1-phenylcyclohex-1-ene 
• 129217-12-5 2(R*)-bromo-1(R*)-methylcyclohexyl benzoylcarbamate 
• 710290-26-9 N-((1R,2S)-2-Hydroxy-cyclohexyl)-4-methoxy-benzamide 
• 51552-22-8 2-methylcyclohex-2-enamine 
• 96304-02-8 2-hydroxy-2-methylcyclohexanone 
• 583-60-8 2-Methylcyclohexanone 

Relevant academic research and scientific papers

Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates

An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine–copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN2′ borylation process catalyzed by a monodentate guanidine–copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.

One-Pot Synthesis of N-Substituted Alkylaminocyclohexanols by the Addition of Electrophiles Formed in situ in the System Н2О2 + HBr (HCl)

Highly selective one-pot synthesis of N-substituted aminocyclohexanols has been performed by hydroxyhalogenation of the corresponding cyclohexenes with electrophilic reagents formed in situ in the system Н2О2 + HHlg (Hlg = Cl, Br), with subsequent substitution of halogen atoms with amines. Some products were tested as antimicrobial additives to motor oils and cooling lubricants and showed high antibacterial and antifungal activity.

(Guanidine)copper Complex-Catalyzed Enantioselective Dynamic Kinetic Allylic Alkynylation under Biphasic Condition

Highly enantioselective allylic alkynylation of racemic bromides under biphasic condition is furnished in this report. This approach employs functionalized terminal alkynes as pro-nucleophiles and provides 6- and 7-membered cyclic 1,4-enynes with high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. Enantioretentive derivatizations highlight the synthetic utility of this transformation. Cold-spray ionization mass spectrometry (CSI-MS) and X-ray crystallography were used to identify some catalytic intermediates, which include guanidinium cuprate ion pairs and a copper-alkynide complex. A linear correlation between the enantiopurity of the catalyst and reaction product indicates the presence of a copper complex bearing a single guanidine ligand at the enantio-determining step. Further experimental and computational studies supported that the alkynylation of allylic bromide underwent an anti-SN2′ pathway catalyzed by nucleophilic cuprate species. Moreover, metal-assisted racemization of allylic bromide allowed the reaction to proceed in a dynamic kinetic fashion to afford the major enantiomer in high yield.

Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists

CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.

Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions

A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri?phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

TRIAZOLYL DERIVATIVES AS SYK INHIBITORS

Provided are triazole derivatives of Formula I which are potent inhibitors of spleen tyrosine kinase and pharmaceutical composition. The triazole derivatives are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone

An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT)

The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.

Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes

A simple one-step method for the preparation of tribromoisocyanuric acid in good yield (87%) has been developed. The reaction of tribromoisocyanuric acid with alkenes in presence of nucleophilic solvents (MeOH, i-PrOH, AcOH and a mixture of H2O-acetone, 1:5) led to the corresponding β-bromoethers, β-bromoacetates and bromohydrins, in high regioselectivity and good yields (73-98%). Georg Thieme Verlag Stuttgart.

A New Regioselective Synthesis of Vicinal Bromohydrins via Free Radical Decarboxylative Bromination of β-Hydroxycarboxylic Acids

Diisopropylcarbodiimide-mediated condensations between N-hydroxypyridine- 2(1H)-thione and β-hydroxycarboxylic acids afforded mixed anhydrides which were regioselectively converted into vicinal bromohydrins under neutral conditions.