138943-51-8

Basic information

• Product Name: 3-Hexen-5-yn-2-ol, 6-phenyl-, acetate
• CAS NO: 138943-51-8
• Molecular Formula: C14H14O2
• Molecular Weight: 214.264
• Mol File: 138943-51-8.mol

Chemical Properties

• CAS DataBase Reference: 3-Hexen-5-yn-2-ol, 6-phenyl-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hexen-5-yn-2-ol, 6-phenyl-, acetate(138943-51-8)
• EPA Substance Registry System: 3-Hexen-5-yn-2-ol, 6-phenyl-, acetate(138943-51-8)

Safety Data

• Hazardous Substances Data: 138943-51-8(Hazardous Substances Data)

Upstream product

• 63124-67-4 (E)-1-phenylhex-4-en-1-yn-3-ol 
• 108-24-7 acetic anhydride 
• 75-05-8 acetonitrile 
• 56963-50-9 (E)-6-Phenyl-hex-3-en-5-yn-2-ol 
• 30625-91-3 (E)-5-phenylpent-2-en-4-ynal 
• 1133296-18-0 acetic acid (E)-1-phenylethynyl-but-2-enyl ester 
• 106949-23-9 (+/-)-6-phenyl-hex-3ξ-en-5-yn-2-ol 

Downstream Products

• 321353-00-8 Acetic acid (E)-(S)-1-methyl-5-phenyl-pent-2-en-4-ynyl ester 

Relevant articles and documents

Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes

Silica gel was found to efficiently promote the rearrangement of allylic acetates into their most stable regioisomers under microwave irradiation. The reaction is easy to perform and eco-friendly. This method was applied to the metal-free synthesis of 1,3-enynes.

Regio- and stereoselective synthesis of vinylallenes by 1,5-(S(N)'')- substitution of enyne acetates and oxiranes with organocuprates

Enyne acetates 2, 4, 6, and 8, as well as enyne oxiranes 10, with different substitution patterns react with organocuprates regioselectively under 1,5-(S(N)2'')-substitution to provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a [formal) transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)-isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions can also be carried out with catalytic amounts of copper reagents. The reaction of chiral enyne acetate (S)-2a with tBu2CuLi · LiCN proceeds enantioselectively, so that this transformation constitutes a new case of remote stereocontrol.

Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles

Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile.Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers.Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane.The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures.The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium.Some preliminary studies indicate that these reactions are proceeding via an ?-allyl complex or tight ion pair rather than a sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.

Cobalt catalyzed regioselective allylation of 1,3-dicarbonyl compounds

Catalytic amount of cobalt(II) chloride in 1,2-dichloroethane promotes the allylation of 1,3-dicarbonyl compounds with allyl acetates in high yields. The allylation of pentane-2,4-dione is highly regioselective as compared with methylacetoacetate and ethyl 2-oxocyclopentanecarboxylate.

COBALT(II) CHLORIDE CATALYSED CONVERSION OF ALLYLIC ALCOHOLS TO REARRANGED ALLYLIC AMIDES

Secondary and tertiary allylic alcohols can be converted to the corresponding allylically rearranged amides and acetates in presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile.Tertiary alcohols undergo complete rearrangement whereas the secondary ones yield a mixture of regioisomers.