17696-11-6Relevant articles and documents
Base- A nd Catalyst-Induced Orthogonal Site Selectivities in Acylation of Amphiphilic Diols
Ashush, Natali,Dobrovetsky, Roman,Fallek, Amit,Fallek, Reut,Portnoy, Moshe
, (2020)
Seeking to selectively functionalize natural and synthetic amphiphiles, we explored acylation of model amphiphilic diols. The use of a nucleophilic catalyst enabled a remarkable shift of the site selectivity from the polar site, preferred in background noncatalyzed or base-promoted reactions, to the apolar site. This tendency was significantly enhanced for organocatalysts comprising an imidazole active site surrounded by long/branched tails. An explanation of these orthogonal modes of selectivity is supported by competitive experiments with monoalcohol substrates.
Synthesis method of ethyl 8-bromocaprylate
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Paragraph 0060; 0065-0067; 0070; 0074-0076; 0078; 0082; ..., (2021/07/10)
The invention provides a synthesis method of ethyl 8-bromocaprylate, which comprises the following steps: S1, carrying out substitution reaction on 1,6-dibromohexane and diethyl malonate to obtain a compound 2-(6-bromohexyl)-diethyl malonate; S2, enabling the 2-(6-bromohexyl)-diethyl malonate to carry out ester hydrolysis and a decarboxylation reaction so as to obtain 8-bromocaprylic acid; and S3, carrying out an esterification reaction on the 8-bromocaprylic acid and absolute ethyl alcohol to obtain ethyl 8-bromocaprylate. According to the synthesis method of ethyl 8-bromocaprylate, disclosed by the embodiment of the invention, firstly, 1,6-dibromohexane initial raw material and diethyl malonate are subjected to substitution reaction to generate 2-(6-bromohexyl) diethyl malonate, and then ester hydrolysis and decarboxylation reaction are carried out to obtain 8-bromocaprylic acid; and finally,esterification reaction is carried out to generate ethyl 8-bromocaprylate. The raw materials are easy to obtain, side reactions in the reaction are few, the process is simple, and the method is suitable for industrial production, and has a very wide application prospect.
Synthesis, antiproliferation, and docking studies of N-phenyl-lipoamide and 8-mercapto-N-phenyloctanamide derivatives: Effects of C6 position thiol moiety
Zhang, Shi-Jie,Hu, Wei-Xiao
, p. 3312 - 3320 (2012/11/07)
Some N-phenyl lipoamide and 8-mercapto- N-phenyloctanamide derivatives were synthesized and their in vitro antiproliferative activity was evaluated. The experimental results indicated that 8-mercapto-N-phenyloctanamides might be good histone deacetylase inhibitors rather than N-phenyl lipoamides, who had thiol moiety at C6 position. To verify the antiproliferation data on structural basis, in silico docking studies of the representative compounds into the crystal structure of histone deacetylase- like protein using AutoDock 4.0 program were performed. Furthermore, sulfur acetylated 8-mercapto-Nphenyloctanamide improved its in vitro antiproliferative activity, probably due to the increasing of its cell membrane permeability. While the identification of enzymatic target of N-phenyl lipoamides with dithiolane is still ongoing. Springer Science+Business Media, LLC 2011.
