1201-92-9

Upstream product

• 24241-74-5 (+/-)-4-hydroxy-4-phenylbutanenitrile 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 23132-29-8 4-oxo-4-phenylbutanamide 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 590-92-1 3-Bromopropionic acid 
• 100-52-7 benzaldehyde 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 26977-05-9 4-amino-1-phenyl-1-butanol 
• 23132-29-8 4-oxo-4-phenylbutanamide 

Relevant academic research and scientific papers

Chromium-mediated aldol and homoaldol reactions on solid support directed towards an iterative polyol strategy

Chromium-Reformatsky and chromium-homoaldol reactions run under neutral and mild reaction conditions. They are highly chemoselective, tolerant towards most common functional groups, and are not prone to retroaldol reactions. Initial studies directed to transfer these homogeneous chromium-mediated solution-phase reactions to solid phase are presented. The main objective was to develop a methodology to aid a combinatorial iterative strategy to polyols (polyketides) on solid phase. A general reactivity problem was observed with polystyrene based resins compared to the solution-phase reactions, independent if the electrophilic (aldehyde) or nucleophilic (bromide) end of the polyol chain was supported to the resin. A complicated penetration, or loss of the polar solvent environment after penetration into the resin, might be responsible for the reduced reactivity. Application of either a soluble polystyrene resin or a polystyrene resin with a polar polyethylene glycol tether resulted in improved yields.

A facile, high yield synthesis of γ- and δ-hydroxyamides

γ- and δ-Hydroxyamides can be prepared in high yields by heating a lactone with ammonia in a pressure tube. The ammonia can be removed by controlled evaporation with ice/acetone cooling.

Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides

Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.

Enantioselective Ruthenium(II)/Xyl-SunPhos/Daipen-Catalyzed hydrogenation of γ-Ketoamides

A0series of γ-hydroxy amides were synthesized with high ena~tioselectivities (up to 99%) usyng asymmetric hydrogenation of the corresponding γ-ketoamides in the presence of Ru-Xyl-SunPhos-Daipen catalyst providing key building blocks for a variety of natu

Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation

To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids were the major products. Unexpectedly, amides were found to be the major products in nitrilase ZmNIT2-catalyzed hydrolysis of β-hydroxy nitriles. The hydrogen bonding between the hydroxyl group and nitrogen in the enzyme-substrate complex intermediates that disfavors the loss of ammonia and formation of acyl-enzyme intermediate, which was further hydrolyzed to acid, was proposed to be responsible for the unprecedented β-hydroxy functionality assisted high yield of amide formation.

Elevation of HDL cholesterol by 4-[(Aminothioxomethyl)-hydrazono]-N-(substituted)-4-arylbutanamides

Compounds of this invention increase plasma levels of high density lipoprotein or HDL, the “good” cholesterol and as such may be useful for treating diseases such as atherosclerosis. These compounds are represented by the formula wherein: R1, R2, and R3are independently hydrogen, C1-C6alkyl, phenyl or —(CH2)1-6phenyl where phenyl is optionally substituted by halogen, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, trifluoromethyl, C1-C6alkoxycarbonyl, —CO2H or OH; R4and R5are independently hydrogen, C1-C10alkyl, C3-C8cycloalkyl, —(CH2)0-6Ar1where Ar1is phenyl, naphthyl, furanyl, pyridinyl or thenyl and Ar1can be optionally substituted by halogen, cyano, nitro, C1-C6alkyl, phenyl, C1-C6alkoxy, phenoxy, trifluoromethyl, C1-C6alkoxycarbonyl, —CO2H or OH, or R4and R5together with the nitrogen to which R4and R5are attached form a ring containing 4-7 carbon atoms; and Ar is phenyl, naphthyl, furanyl, pyridinyl or thienyl which may be optionally substituted by halogen, cyano, nitro, C1-C6alkyl, C3-C6cycloalkyl, phenyl, C1-C6alkoxy, phenoxy, trifluoromethyl, C1-C6alkoxycarbonyl, —CO2H or OH.

Elevation of HDL cholesterol by N-[4-[(aminothioxomethyl) hydrazono]-4-arylbutyl]amides

This invention relates to the treatment of atherosclerosis via raising the level of HDL cholesterol by administration of a compound of the formula wherein: R1, R2, and R3 are independently hydrogen, C1-C6 alkyl or -(CH2)0-6Ph where Ph is phenyl is optiona