87073-90-3

Basic information

• Product Name: Cyclohexanemethanol, 4-phenyl-, trans-
• Synonyms: (4t-Phenyl-cyclohexyl-(1r))-methanol;trans-1-Hydroxymethyl-4-phenyl-cyclohexan;(4-Phenyl-cyclohexyl)-methanol
• CAS NO: 87073-90-3
• Molecular Formula: C13H18O
• Molecular Weight: 190.285
• Mol File: 87073-90-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 310.7±11.0 °C(Predicted)
• Density: 1.005±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Cyclohexanemethanol, 4-phenyl-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanemethanol, 4-phenyl-, trans-(87073-90-3)
• EPA Substance Registry System: Cyclohexanemethanol, 4-phenyl-, trans-(87073-90-3)

Safety Data

• Hazardous Substances Data: 87073-90-3(Hazardous Substances Data)

Upstream product

• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 873949-18-9 ethyl 4-phenyl-1-cyclohexenecarboxylate 
• 22748-63-6 1,2,3,6-tetrahydro-[1,1′-biphenyl]-4-carbonitrile 
• 1082673-09-3 ethyl 4-phenylcyclohexane-1-carboxylate 
• 50-00-0 formaldehyd 
• 3132-99-8 m-bromobenzoic aldehyde 
• 1466-74-6 4‐phenylcyclohexan‐1‐carbaldehyde 
• 701232-23-7 [4-(methoxymethylidene)cyclohexyl]benzene 
• 110-83-8 cyclohexene 
• 23923-62-8 cis e trans-4-fenilacetilcicloesano 
• 1466-73-5 trans-4-phenylcyclohexanecarboxylic acid 
• 73011-77-5 trans-4-phenylcyclohexanecarboxylic acid ethyl ester 
• 36296-69-2 trans-4-phenylcyclohexanecarboxylic acid methyl ester 
• 829-27-6 3-phenylpentane-1,5-diol 

Downstream Products

• 1071938-98-1 C₁₄H₁₈O 
• 87090-92-4 ((1r,4r)-4-phenylcyclohexyl)methyl 4-methylbenzenesulfonate 
• 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 articles and documents

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 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.

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.