87073-90-3

Upstream product

• 73011-77-5 trans-4-phenylcyclohexanecarboxylic acid ethyl ester 
• 701232-23-7 [4-(methoxymethylidene)cyclohexyl]benzene 
• 1466-74-6 4‐phenylcyclohexan‐1‐carbaldehyde 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 50-00-0 formaldehyd 
• 3132-99-8 m-bromobenzoic aldehyde 
• 873949-18-9 ethyl 4-phenyl-1-cyclohexenecarboxylate 
• 110-83-8 cyclohexene 
• 23923-62-8 cis e trans-4-fenilacetilcicloesano 
• 1466-73-5 trans-4-phenylcyclohexanecarboxylic acid 
• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 36296-69-2 trans-4-phenylcyclohexanecarboxylic acid methyl ester 
• 22748-63-6 1,2,3,6-tetrahydro-[1,1′-biphenyl]-4-carbonitrile 
• 829-27-6 3-phenylpentane-1,5-diol 

Downstream Products

• 87090-92-4 ((1r,4r)-4-phenylcyclohexyl)methyl 4-methylbenzenesulfonate 
• 1071938-98-1 C₁₄H₁₈O 
• 145693-34-1 1-acetomethyl-4-(4-acetylphenyl)cyclohexane 
• 145693-36-3 4-(4-chloromethylcyclohexyl)benzamide 
• 145693-35-2 4-(4-hydroxymethylcyclohexyl)benzoic acid 
• 93205-87-9 1-chloromethyl-4-(4-cyanophenyl)cyclohexane 

Relevant academic research and scientific papers

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach

A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.

Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy

An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.

Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes

This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes.

Discovery of 6-phenylpyrimido[4,5- B ][1,4]oxazines as potent and selective Acyl CoA: Diacylglycerol acyltransferase 1 (DGAT1) inhibitors with in vivo efficacy in rodents

The discovery and optimization of a series of acyl CoA:diacylglycerol acyltransferase 1 (DGAT1) inhibitors based on a pyrimido[4,5-b][1,4]oxazine scaffold is described. The SAR of a moderately potent HTS hit was investigated resulting in the discovery of phenylcyclohexylacetic acid 1, which displayed good DGAT1 inhibitory activity, selectivity, and PK properties. During preclinical toxicity studies a metabolite of 1 was observed that was responsible for elevating the levels of liver enzymes ALT and AST. Subsequently, analogues were synthesized to preclude the formation of the toxic metabolite. This effort resulted in the discovery of spiroindane 42, which displayed significantly improved DGAT1 inhibition compared to 1. Spiroindane 42 was well tolerated in rodents in vivo, demonstrated efficacy in an oral triglyceride uptake study in mice, and had an acceptable safety profile in preclinical toxicity studies.

Stereoselective Metal Catalysed Hydroboration of 4-Substituted 1-Methylidenecyclohexanes

Rhodium catalysed hydroboration of 4-substituted 1-methylidenecyclohexanes gives cis-hydroboration products with high stereoselectivity.The effects influencing the stereochemistry are discussed.

LIQUID-CRYSTALLINE COMPOUNDS OF THE ALICYCLIC SERIES III. SYNTHESIS AND ISOMORPHISM OF ETHERS AND ESTERS CONTAINING THE PHENYLCYCLOHEXANE FRAGMENT

A series of ethers and esters exhibiting mesomorphous characteristics were obtained from para-X-substituted trans-4-phenylcyclohexanols, trans-4-phenylcyclohexanecarboxylic acids (X = H, F, I, NO2, NH2, CN) and trans-1-hydroxymethyl-4-(p-cyanophenyl)cyclohexane.