106180-32-9

Upstream product

• 106180-71-6 2-[1-Isopropoxy-meth-(Z)-ylidene]-1-phenylethynyl-cycloheptanol 
• 85236-13-1 2-bromocyclohept-1-ene-1-carbaldehyde 
• 536-74-3 phenylacetylene 
• 502-42-1 cycloheptanone 
• 65519-66-6 2-(Isopropoxymethylene)-cycloheptanone 
• 934-20-3 (2Z)-2-(hydroxymethylene)cycloheptanone 

Downstream Products

• 106180-46-5 (E)/(Z)-3-<(2-Phenylethynyl)-1-cycloheptenyl>-oxirane-2-carbonitrile 
• 106180-46-5 (E)-3-<2-(2-Phenylethynyl)-1-cycloheptenyl>-oxirane-2-carbonitrile 
• 106180-46-5 (Z)-3-<2-(2-Phenylethynyl)-1-cycloheptenyl>-oxirane-2-carbonitrile 
• 196407-38-2 3-Phenyl-1-(2-phenylethynyl-cyclohept-1-enyl)-prop-2-yn-1-ol 
• 1207093-56-8 C₁₆H₁₆O₂ 
• 196407-36-0 1-(2-Phenylethynyl-cyclohept-1-enyl)-hept-2-yn-1-ol 

Relevant academic research and scientific papers

Ring size effects in the C2-C6 biradical cyclisation of enyne-allenes and the relevance for neocarzinostatin

The regioselectivity of the thermal cyclisations of enyne-allenes 1 can be toggled as a function of the ring size of the cycloalkene. With a cyclopentene as the ene moiety the Myers-Saito (C2-C7) cycloaromatisation product is formed, whereas with six- and seven-membered cycloalkenes the novel C2-C6 cyclisation is observed. DFT calculations are used to rationalise these changes. The implications of these findings for alternative thermal biradical cyclisations of neocarzinostatin are discussed.

Copper-catalyzed addition of water affording highly substituted furan and unusual formation of naphthofuran ring from 3-(1-alkenyl)-2-alkene-1-al

We have developed a novel one-pot reaction to generate highly substituted furan through the addition of water followed by oxidation and unusual cyclization to naphthofuran ring under the same reaction condition.

Ring strain effects in enyne-allene thermolysis: Switch from the Myers-Saito reaction to the C2-C6 biradical cyclization

The mode of the thermal cyclization of enyne-allenes 1 depends on ring strain effects: when the ene functionality is part of a benzene, cyclohexene or cycloheptene ring the novel C2-C6 biradical cyclization is observed, while when it is part of a cyclopentene ring the Myers-Saito cycloaromatization is registered.

THERMALLY INITIATED REACTIONS OF (Z)-EPOXYHEXENYNES A FACILE PREPARATION OF 3,4-ANNULATED FURANS

An efficient and general access to 3,4-annulated 2-vinylfurans (type II) is provided by the thermally induced ring transformation of epoxyhexenynes (I).Depending on the substitution pattern the reactions proceed either by heating in solution (5a-h) or under short-time thermolysis conditions (6i, j).The results are consistent with a multistep mechanism involving 1-oxacyclohepta-3,4,6-trienes as central intermediates.