81532-80-1

Basic information

• Product Name: 3-Butyn-2-one, 4-(4-methoxyphenyl)-
• CAS NO: 81532-80-1
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• Mol File: 81532-80-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 3-Butyn-2-one, 4-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butyn-2-one, 4-(4-methoxyphenyl)-(81532-80-1)
• EPA Substance Registry System: 3-Butyn-2-one, 4-(4-methoxyphenyl)-(81532-80-1)

Safety Data

• Hazardous Substances Data: 81532-80-1(Hazardous Substances Data)

Upstream product

• 768-60-5 4-methoxyphenylacetylen 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 141-78-6 ethyl acetate 
• 111887-18-4 4-(4-methoxyphenyl)but-3-yn-2-ol 
• 108-24-7 acetic anhydride 
• 696-62-8 para-iodoanisole 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 74-88-4 methyl iodide 
• 134613-38-0 (Z)-3-Isopropylamino-1-(4-methoxy-phenyl)-but-2-en-1-one 

Downstream Products

• 681432-04-2 1-[2-(4-methoxyphenyl)pyrazolo[1,5-b]pyridazin-3-yl]ethanone 
• 913185-54-3 3,4-bis(4-methoxybenzoyl)hex-3-ene-2,5-dione 
• 1189116-43-5 1-cyano-2-(4-methoxybenzylidene)-3-oxo-5-phenylcyclopentanecarboxylic acid ethyl ester 
• 1224854-00-5 4-(1-methyl-1-phenylinden-3-yl)phenol 

Relevant articles and documents

Cobalt-Catalyzed Chemo- and Enantioselective Hydrogenation of Conjugated Enynes

Asymmetric hydrogenation is one of the most powerful methods for the preparation of single enantiomer compounds. However, the chemo- and enantioselective hydrogenation of the relatively inert unsaturated group in substrates possessing multiple unsaturated bonds remains a challenge. We herein report a protocol for the highly chemo- and enantioselective hydrogenation of conjugated enynes while keeping the alkynyl bond intact. Mechanism studies indicate that the accompanying Zn2+ generated from zinc reduction of the CoII complex plays a critical role to initiate a plausible CoI/CoIII catalytic cycle. This approach allows for the highly efficient generation of chiral propargylamines (up to 99.9 % ee and 2000 S/C) and further useful chemical transformations.

Lewis-base-catalysed selective reductions of ynones with a mild hydride donor

Ynones are efficiently reduced with a mild hydride donor in the presence of a catalytic amount of nucleophilic phosphines. The reactions are selective 1,2-reductions that give propargyl alcohols in yields of up to 96%. It is proposed that success in these reactions depends on the activation of ynones by a Lewis base catalyst. A protic additive plays a key role in suppressing the undesired reaction pathways and accelerating the 1,2-reductions.

Gold-catalyzed N,O-functionalization of 1,4-diyn-3-ols with: N -hydroxyanilines to form highly functionalized pyrrole derivatives

This work describes new N,O-functionalization of 1,4-diyn-3-ols with N-hydroxyanilines to yield highly functionalized pyrrole derivatives. In a postulated mechanism, N-hydroxyaniline attacks the more electron-rich alkynes via regioselective N-attack to form unstable ketone-derived nitrones that react with their tethered alkynes via an intramolecular oxygen-transfer to form α-oxo gold carbenes. This new method is applicable to a short synthesis of a bioactive molecule, a PDE4 inhibitor.