139224-56-9

Upstream product

• 4233-09-4 2-phenyl-4,6-dimethyl-1,3-dioxane 
• 625-33-2 3-penten-2-one 
• 100-51-6 benzyl alcohol 
• 123826-84-6 4-(benzyloxy)pentan-2-ol 

Downstream Products

• 139224-42-3 (R*,S*)-2-Benzylamino-4-benzyloxy-2-methylpentanenitrile 
• 139224-42-3 (R*,R*)-2-Benzylamino-4-benzyloxy-2-methylpentanenitrile 
• 1205544-64-4 methyl 4-(5-(benzyloxy)3-(methoxycarbonyloxy)-3-methylhex-1-ynyl)benzoate 
• 139224-50-3 (3R,5S)-3-Benzylamino-3,5-dimethyl-dihydro-furan-2-one 
• 139224-50-3 (3R,5R)-3-Benzylamino-3,5-dimethyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Intramolecular OH...Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif

Fluorination is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen-bond (HB) properties of adjacent functional groups, as well as the HB-accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH...F intramolecular HBs (IMHBs) has been established for conformationally restricted fluorohydrins, such interaction in flexible compounds remained questionable. Herein is demonstrated for the first time - and in contrast to earlier reports - the occurrence of OH...F IMHBs in acyclic saturated γ-fluorohydrins, even for the parent 3-fluoropropan-1-ol. The relative stereochemistry is shown to have a crucial influence on the corresponding h1JOH...F values, as illustrated by syn- and anti-4-fluoropentan-2-ol (6.6 and 1.9 Hz). The magnitude of OH...F IMHBs and their strong dependence on the overall molecular conformational profile, fluorination motif, and alkyl substitution level, is rationalized by quantum chemical calculations. For a given alkyl chain, the "rule of shielding" applies to OH...F IMHB energies. Surprisingly, the predicted OH...F IMHB energies are only moderately weaker than these of the corresponding OH...OMe. These results provide new insights of the impact of fluorination of aliphatic alcohols, with attractive perspectives for rational drug design.

Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones

A series of acidic-functionalized ionic liquids were synthesized and applied to the hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones under solvent-free conditions. Notably, 1-methylimidazolium p-toluenesulfoni

Benzo[e]isoindole-1,3-diones as potential inhibitors of glycogen synthase kinase-3 (GSK-3). Synthesis, kinase inhibitory activity, zebrafish phenotype, and modeling of binding mode

Benzo[e]isoindole-1,3-dione derivatives were synthesized, and the effects on GSK-3β activity and zebrafish embryo growth were evaluated.Aseries of derivatives show obvious inhibitory activity against GSK-3β. The most potent inhibitor, 7,8-dimethoxy-5-methylbenzo[e]isoindole-1,3-dione (8a), shows nanomolar IC50 and obvious phenotype on zebrafish embryo growth associated with the inhibition of GSK-3β at low micromolar concentration. The interaction mode between 8a and GSK-3β was characterized by computational modeling. 2009 American Chemical Society.

1,5-Asymmetric induction in boron-mediated aldol reactions of β-alkoxy methylketones

(Chemical Equation Presented) Good levels of substrate-controlled, 1,5-syn-stereoinduction are obtained in boron-mediated aldol reactions of β-trichloromethyl-β-alkoxy and β-trifluoromethyl-β-alkoxy methylketones with achiral aldehydes, independent of the nature of the β-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of β-aryl-β-alkoxy methylketones, the 1,5-anti-adducts were obtained with high levels of diastereoselectivity only with a β-OPMB group.

High Thermodynamic Diastereoselection in the Equilibration of Acyclic γ-Alkoxy α-Amino nitriles

An equilibrium between two diastereomers of an acyclic γ-alkoxy α-amino nitrile was attained in chloroform, and the major component is always its (R*,S*)-isomer with high diastereoselectivity.