266325-23-9

Basic information

• Product Name: ethyl (E)-6-phenylhex-2-en-5-ynoate
• Synonyms: ethyl (E)-6-phenylhex-2-en-5-ynoate
• CAS NO: 266325-23-9
• Molecular Weight: 214.264
• Mol File: 266325-23-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl (E)-6-phenylhex-2-en-5-ynoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (E)-6-phenylhex-2-en-5-ynoate(266325-23-9)
• EPA Substance Registry System: ethyl (E)-6-phenylhex-2-en-5-ynoate(266325-23-9)

Safety Data

• Hazardous Substances Data: 266325-23-9(Hazardous Substances Data)

Upstream product

• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 420121-38-6 methyl (3-phenylprop-2-yn-1-yl) carbonate 
• 673-32-5 1-Phenylprop-1-yne 
• 31930-36-6 ethyl (E)-3-iodopropenoate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 

Relevant articles and documents

Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- And Alkynylsilanes under Gold Catalysis: Regio- And Stereoselective Synthesis of Skipped Dienes and Enynes

We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon-carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)-C(sp3) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.

Unusual regioselectivity of Pd(0)-catalyzed coupling reaction of electron-deficient alkenyl halides with allenic/propargylic zinc reagents. Highly selective synthesis of 6-phenylhex-5-yn-2(or 3)-enoates/enitrile and 4-phenyl-6-substituted-hexa-2,4,5-trienoates

The Pd(0)-catalyzed coupling reaction of electron-deficient alkenyl halides with the organozinc formed by the subsequent treatment of 1- phenylalk-1-yne with n-BuLi and ZnBr2 with or without a catalytic amount of HgCl2 was studied. Both the allene-formation- and the alkyne-formation-type coupling reactions were observed with high regio- and stereoselectivity: the reaction of 1-phenylprop-1-yne afforded 6-phenylhex-5-yn-2(or 3)-enoates and -enitriles, while the reaction of 1-phenylhex-1-yne formed 4-phenyl-6- substituted-hexa-2,4,5-trienoates. A plausible explanation for the regioselectivity was discussed. The double bonds in 6-phenylhex-5-yn-2- enoates were prone to migrate to the position conjugated with the carbon- carbon triple bonds to form 6-phenylhex-5-yn-3-enoates at higher temperature. The migration did not occur in absence of an excess amount of allenic/propargylic zinc reagent or at low temperature.