60096-90-4

Upstream product

• 56229-85-7 N,N-diethyl-4-phenylbutanamide 
• 123-30-8 4-amino-phenol 
• 300-57-2 allylbenzene 
• 201230-82-2 carbon monoxide 
• 637-50-3 1-phenylpropene 
• 1821-12-1 4-Phenylbutyric acid 

Relevant academic research and scientific papers

Tungsten-Catalyzed Transamidation of Tertiary Alkyl Amides

Transamidation has recently emerged as a straightforward and convenient means to diversify amides. However, the kinetically and thermodynamically demanding transamidation of notoriously robust, fully alkyl-substituted tertiary amides still remains a longstanding challenge. Here, we describe a method for the activation of tertiary alkyl amides to streamline transamidation using simple tungsten(VI) chloride as a catalyst and chlorotrimethylsilane as an additive. The highly electrophilic and oxophilic tungsten catalyst enables the selective scission of a C-N bond of tertiary alkyl amides to effect transamidation of a myriad of structurally and electronically diverse tertiary alkyl amides and amines. Mechanistic study implies that the synergistic effect of the catalyst and the additive could pronouncedly induce the nucleophilic acyl substitution of tertiary alkyl amide with amine to realize transamidation.

Highly Ligand-Controlled Regioselective Pd-Catalyzed Aminocarbonylation of Styrenes with Aminophenols

Achieving chemo- and regioselectivity simultaneously is challenging in organic synthesis. Transition metal-catalyzed reactions are effective in addressing this problem by the diverse ligand effect on the catalyst center. Ligand-controlled regioselective Pd-catalyzed carbonylation of styrenes with aminophenols was realized, chemoselectively affording amides. Using a combination of boronic acid and 5-chlorosalicylic acid as the additives, linear amides were obtained in high yields and selectivity using tris(4-methoxyphenyl)phosphine (L3) in acetonitrile, while branched amides were obtained in high yields and selectivity in butanone by changing the ligand to 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane (L5). Further studies show that the nature of the ligand is key to the regioselectivity. Cone angle and Tolman electronic parameter (TEP) have been correlated to the reactivity and regioselectivity. Studies on the acid additives show that different acids act as the proton source and the corresponding counterion can help enhance the reactivity and selectivity.

Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor

Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction lies in the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.