2528-36-1Relevant academic research and scientific papers
Synthesis, biochemical evaluation, and molecular modeling studies of aryl and arylalkyl di-n-butyl phosphates, effective butyrylcholinesterase inhibitors
Nakayama, Kensaku,Schwans, Jason P.,Sorin, Eric J.,Tran, Trina,Gonzalez, Jeannette,Arteaga, Elvis,McCoy, Sean,Alvarado, Walter
, p. 3171 - 3181 (2017/05/29)
A series of dialkyl aryl phosphates and dialkyl arylalkyl phosphates were synthesized. Their inhibitory activities were evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The di-n-butyl phosphate series consistently displayed selective inhibition of BChE over AChE. The most potent inhibitors of butyrylcholinesterase were di-n-butyl-3,5-dimethylphenyl phosphate (4b) [KI?=?1.0?±?0.4?μM] and di-n-butyl 2-naphthyl phosphate (5b) [KI?=?1.9?±?0.4?μM]. Molecular modeling was used to uncover three subsites within the active site gorge that accommodate the three substituents attached to the phosphate group. Phosphates 4b and 5b were found to bind to these three subsites in analogous fashion with the aromatic groups in both analogs being accommodated by the “lower region,” while the lone pairs on the P[dbnd]O oxygen atoms were oriented towards the oxyanion hole. In contrast, di-n-butyl-3,4-dimethylphenyl phosphate (4a) [KI?=?9?±?1?μM], an isomer of 4b, was found to orient its aromatic group in the “upper left region” subsite as placement of this group in the “lower region” resulted in significant steric hindrance by a ridge-like region in this subsite. Future studies will be designed to exploit these features in an effort to develop inhibitors of higher inhibitory strength against butyrylcholinesterase.
CDI-promoted direct esterification of P(O)-OH compounds with phenols
Xiong, Biquan,Hu, Chenghong,Li, Haotian,Zhou, Congshan,Zhang, Pangliang,Liu, Yu,Tang, Kewen
supporting information, p. 2482 - 2486 (2017/05/31)
A novel and efficient N,N′-carbonyl diimidazole-catalyzed protocol for the direct esterification of P(O)-OH compounds using phenols as efficient esterification reagents is illustrated. It is a simple way to synthesis a broad spectrum of functionalized O-aryl phosphinates, phosphonates, and phosphates from basic starting materials with moderate to excellent yields.
Copper-catalyzed direct esterification of P(O)-OH compounds with phenols
Xiong, Biquan,Zeng, Kui,Zhang, Shanshan,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
supporting information, p. 9293 - 9298 (2015/11/27)
A novel copper-catalyzed method for the direct esterification of P(O)-OH compounds using phenols as efficient esterification reagents is illustrated. It is a simple way to generate a broad spectrum of functionalized O-aryl phosphinates, phosphonates, and phosphates from basic starting materials with moderate to excellent yields.
Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates
Xiong, Biquan,Feng, Xiaofeng,Zhu, Longzhi,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
, p. 537 - 543 (2015/04/14)
Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.
Aerobic photooxidation of phosphite esters using diorganotelluride catalysts
Oba, Makoto,Okada, Yasunori,Nishiyama, Kozaburo,Ando, Wataru
supporting information; experimental part, p. 1879 - 1881 (2009/10/10)
Diorganotellurides containing bulky aromatic substituents are found to catalyze the photooxidation of phosphite esters using aerobic oxygen as a terminal oxidant. A Hammett plot with substituted triaryl phosphites yielding p = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.2009 American Chemical Society.
Catalytic Hydrolysis of Phosphate Esters in Microemulsions. 3. Analysis of the Hydrolysis Products of p-Nitrophenyl Diphenyl Phosphate via 31P NMR
Burnside, Beth A.,Szafraniec, Linda L.,Knier, Barry L.,Durst, H. Dupont,Mackay, Raymond A.,Longo, F.R.
, p. 2009 - 2011 (2007/10/02)
An analysis of the hydrolysis products of p-nitrophenyl diphenyl phosphate (PNDP) in three different microemulsions via 31P NMR has proven that diphenyl phosphate is the major product and that p-nitrophenyl phenyl phosphate is the second most abundant product in each of the three media.For the media containing butanol, butyl diphenyl phosphate is observed as a third primary product.Numerous secondary products result from the hydrolysis of butyl diphenyl phosphate.
Selective phosphorylation process
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, (2008/06/13)
A one step process for the preparation of phosphate esters of phenol comprising reacting phenol with a dimethyl disulfide and a trialkyl phosphite.
