208924-64-5

Upstream product

• 25145-43-1 2-phenylpropionyl chloride 
• 492-37-5 hydratropic acid 
• 95826-99-6 1-(1H-imidazol-1-yl)-2-phenylpropan-1-one 
• 154569-24-1 2,5-dioxo-pyrrolidin-1-yl 2-phenylpropanoate 
• 34713-70-7 2-Phenylpropanal 

Downstream Products

• 153992-22-4 allyl N-(1-phenylethyl)carbamate 
• 14649-03-7 1-phenylethylisocyanate 
• 1504-06-9 3-methylindolin-2-one 
• 121726-55-4 N-Acetoxy-2-phenyl-propionamide 

Relevant academic research and scientific papers

1,3,2-Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids

The potent nucleophilicity and remarkably low basicity of 1,3,2-diazaphospholenes (DAPs) is exploited in a catalytic, metal-free 1,4-reduction of free α,β-unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the carboxylic acid moiety and hence does not consume an additional hydride equivalent. This highlights the excellent nucleophilic character and low basicity of DAP-hydrides. Functional groups such as Cbz group or alkyl halides which can be problematic with classical transition-metal catalysts are well tolerated in the DAP-catalyzed process. Moreover, the transformation is characterized by a low catalyst loading, mild reaction conditions at ambient temperature as well as fast reaction times and high yields. The proof-of-principle for a catalytic enantioselective version is described.

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

One-pot synthesis of hydroxamic acids from aldehydes and hydroxylamine

A one-pot oxidative transformation of aldehydes into hydroxamic acids by the use of an aqueous solution of hydroxylamine is reported. The methodology gives high yields and makes use of cheap, abundant and easily available reagents.

N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement

An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors

We have identified a series of diphenylmethylene hydroxamic acids as novel and selective HDAC class IIa inhibitors. The original hit, N-hydroxy-2,2-diphenylacetamide (6), has sub-micromolar class IIa HDAC inhibitory activity, while the rigidified oxygen a

Solid supported synthesis of hydroxamic acids

A novel approach to the solid supported synthesis of hydroxamic acids was developed. It employs oxime resin and unlike all previously reported methods allows for the use of acid labile protecting groups. Cleavage is induced by treatment with tert-butyldim