276669-67-1

Basic information

• Product Name: 1-ethynyl-4-phenylcyclohexan-1-ol
• Synonyms: 1-ethynyl-4-phenylcyclohexan-1-ol
• CAS NO: 276669-67-1
• Molecular Weight: 200.28
• Mol File: 276669-67-1.mol

Chemical Properties

• CAS DataBase Reference: 1-ethynyl-4-phenylcyclohexan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethynyl-4-phenylcyclohexan-1-ol(276669-67-1)
• EPA Substance Registry System: 1-ethynyl-4-phenylcyclohexan-1-ol(276669-67-1)

Safety Data

• Hazardous Substances Data: 276669-67-1(Hazardous Substances Data)

Upstream product

• 4894-75-1 1-phenyl-4-cyclohexanone 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 1082207-61-1 C₁₆H₁₈O₃ 
• 1130782-30-7 4-ethynyl-1,2,3,6-tetrahydro-1,1'-biphenyl 
• 1082207-43-9 (4-vinylidenecyclohexyl)benzene 

Relevant articles and documents

Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones

The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling

The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.

Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex

Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful β,γ-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of σ-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO2 in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol. Copyright