14132-50-4

Upstream product

• 93698-13-6 α-d₂-3-phenylpropiophenone 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 17537-31-4 Acetophenone-methyl-d3 
• 3240-11-7 Phenylacetylene-d1 
• 536-74-3 phenylacetylene 
• 611-91-6 2,3-dibromo-1,3-diphenylpropane-1-one 
• 32147-20-9 (Z)-2-bromo-1,3-diphenylprop-2-en-1-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 70-11-1 α-bromoacetophenone 
• 101957-56-6 Benzoylmethyl-d2-triphenyl-phosphonium-bromid 
• 6048-29-9 triphenylphenacylphosphonium bromide 
• 27653-98-1 2-deuterio-1-phenyl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 

Downstream Products

• 1401797-70-3 C₂₁H₁₆⁽²⁾HNO₂S 

Relevant academic research and scientific papers

Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes

The substituent effects on the reactions of permanganate ion with unsymmetrical alkenes are analyzed on the assumption of a concerted (3 + 2) cycloaddition model by using an equation obtained by approximation based on the FMO theory in which development and localization of the frontier molecular orbitals at the reaction sites with progress of the reaction are considered. The Hammett plots are successfully reproduced with the newly obtained rate data for the reactions of trans-chalcone and its derivatives and the data for methyl cinnamates, cinnamate ions, and alkyl vinyl ethers taken from the literature using FMO energies and orbital coefficients calculated by the PM3 method. It was indicated that a factor introduced to the basic equation in order to estimate the extent of localization of the molecular orbitals at the transition state is closely related to the position of the transition state along the reaction path.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Regioselective α-Deuteration of Michael Acceptors Mediated by Isopropylamine in D2O/AcOD

Site-specific hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features D2O and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle motifs as well as enones. The method has been applied to the synthesis of deuterated drug precursors.

Cu-catalyzed sequential dehydrogenation-conjugate addition for β-functionalization of saturated ketones: Scope and mechanism

The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.

Tin(II) chloride mediated coupling reactions between alkynes and aldehydes

Tin(II) chloride, which is insensitive to water and air, mediated the coupling reaction between alkynes and aldehydes as a Lewis acid in nitromethane to produce (E)-α,β-unsaturated ketones by a skeletal transformation in which one alkynic carbon atom changed into an oxo carbon atom accompanied by the cleavage of a C=O bond in the starting aldehydes. This coupling reaction was promoted by a catalytic amount of a primary or secondary alkanol. The coupling reaction between 1-deuterio-2-phenylethyne and benzaldehyde with BuOH afforded 1,3-diphenyl-2-deuterio-2-propenone (2-deuteriation: 94 % D), whereas the coupling reaction between phenylethyne and benzaldehyde with BuOD afforded 1,3-diphenyl-2-propenone (2-deuteriation: 0 % D). Because almost no exchange between hydrogen and deuterium at the 2-position of 1,3-diphenyl-2-propenone occurs in either of the reactions, the coupling reaction between alkynes and aldehydes with tin(II) chloride is presumed to proceed by nucleophilic addition of alkynes to aldehydes. The cleavage of the C-O single bond generated by the nucleophilic addition might be induced by the strong oxophilicity of tin. Coupling reactions occur between alkynes and aldehydes mediated by tin(II) chloride as a Lewis acid to produce (E)-α,β-unsaturated ketones by a skeletal transformation in which an alkynic carbon atom changes into an oxo carbon atom accompanied by cleavage of the C=O bond in the starting aldehydes. This coupling reaction is promoted by a catalytic amount of a primary or secondary alkanol. Copyright

[4+2] Annulation of vinyl ketones initiated by a phosphine-catalyzed aza-Rauhut-currier reaction: A practical access to densely functionalized tetrahydropyridines

The first example of phosphine catalyzed aza-Rauhut-Currier reaction initiated [4+2] annulation of vinyl ketones with N-sulfonyl-1-aza-1,3-dienes has been disclosed. Under the ambient conditions, this protocol provides a practical access to valuable densely functionalized tetrahydropyridines in good to excellent yields and high diastereoselectivities (see scheme). Copyright

Indium(III)-catalyzed coupling between alkynes and aldehydes to α,β-unsaturated ketones

The combined use of a catalytic amount of InX3 (X = OTf and NTf2) and 1-butanol was found to be effective in formal alkynealdehyde metathesis. With this catalytic system, aromatic alkynes reacted with aromatic aldehydes to give chalcones in moderate to good yields. Alkynals were efficiently converted into 5- to 7-membered cyclic compounds by intramolecular alkyne-aldehyde coupling.

Configurations and Conformations of the Oximes, O-Methyl Oximes, and N-Methylnitrones derived from Chalcones

The E- and Z-oximes, O-methyl oximes, and N-methylnitrones of (E)-Chalcone and its 4-MeO, 4-NO2, 4'-MeO, and 4'-NO2 derivatives have been synthesized and examined by u.v. and 1H and 13C n.m.r. spectroscopy.It is concluded that all these compounds exist in