72946-37-3

Basic information

• Product Name: Cycloheptanol, 1-(phenylethynyl)-
• CAS NO: 72946-37-3
• Molecular Formula: C15H18O
• Molecular Weight: 214.307
• Mol File: 72946-37-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Cycloheptanol, 1-(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cycloheptanol, 1-(phenylethynyl)-(72946-37-3)
• EPA Substance Registry System: Cycloheptanol, 1-(phenylethynyl)-(72946-37-3)

Safety Data

• Hazardous Substances Data: 72946-37-3(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 502-42-1 cycloheptanone 
• 4440-01-1 lithium phenylacetylide 

Downstream Products

• 853994-91-9 1-(2-phenylethynyl)-8-oxabicyclo[5.1.0]octane 
• 502-42-1 cycloheptanone 
• 1603105-46-9 3-methyl-3-(3-phenylprop-2-yn-1-yl)-2,3-dihydrobenzofuran 
• 1114060-70-6 1-allyl-1-phenylethynylcycloheptane 

Relevant articles and documents

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades

A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate's tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Additionally, propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement.

DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source

A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.