di-n-butyl m-methylbenzyl phosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: di-n-butyl m-methylbenzyl phosphate
• 英文别名: dibutyl (3-methylbenzyl)phosphate；di-n-butyl 3-methylbenzyl phosphate；Dibutyl (3-methylphenyl)methyl phosphate；dibutyl (3-methylphenyl)methyl phosphate
• 化学式: C₁₆H₂₇O₄P
• 分子量: 314.362
• InChiKey: FNTYUIHYKIXGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间二甲苯 、 磷酸二丁酯 在 二叔丁基过氧化物 、 十六烷基三甲基溴化铵 作用下， 反应 10.0h， 以77%的产率得到di-n-butyl m-methylbenzyl phosphate
  参考文献：
  名称：

  十六烷基三甲基溴化铵催化甲基芳烃中的苄基C（sp 3）-H键与P（O）-OH化合物的氧化交叉脱氢偶联

  摘要：

  有机磷化合物的合成的高效无金属方法通过苄型C（SP的氧化交脱氢偶联3报道）-H债券methylarenes用P（O）-OH的化合物通过十六烷基三甲基溴化铵（CTAB）催化。反应中可耐受各种甲基芳烃和P（O）-OH化合物，产率中等至良好。与以前的研究相比，本研究扩展了底物的范围，并采用了铵盐催化剂（CTAB）和氧化剂（DTBP）的新反应体系。控制和机械实验的结果通常与提出的总体途径一致。该方法可避免使用有毒的P卤素试剂和P（O）-H化合物来合成有机磷化合物。

  DOI：

  10.1039/c8ob02772b

文献信息

• Synthesis, biochemical evaluation, and molecular modeling studies of aryl and arylalkyl di- n -butyl phosphates, effective butyrylcholinesterase inhibitors
  作者：Kensaku Nakayama、Jason P. Schwans、Eric J. Sorin、Trina Tran、Jeannette Gonzalez、Elvis Arteaga、Sean McCoy、Walter Alvarado

  DOI：10.1016/j.bmc.2017.04.002

  日期：2017.6

  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) [ICy = 1.0 0.4 LM] and di-n-butyl 2-naphthyl phosphate (5b) [K-t=1.9 0.4 I.L.M]. 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=0 oxygen atoms were oriented towards the oxyanion hole. In contrast, din-butyl-3,4-dimethylphenyl phosphate (4a) [K = 9 111M], 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. (C) 2017 Elsevier Ltd. All rights reserved.
• Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp³)–H bonds in methylarenes with P(O)–OH compounds
  作者：Hang Li、Jian Lei、Yongping Liu、Yi Chen、Chak-Tong Au、Shuang-Feng Yin

  DOI：10.1039/c8ob02772b

  日期：——

  An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)–H bonds in methylarenes with P(O)–OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is reported. Various methylarenes and P(O)–OH compounds are tolerated in the reaction with moderate to good yields. Compared to previous studies, the present study

  有机磷化合物的合成的高效无金属方法通过苄型C（SP的氧化交脱氢偶联3报道）-H债券methylarenes用P（O）-OH的化合物通过十六烷基三甲基溴化铵（CTAB）催化。反应中可耐受各种甲基芳烃和P（O）-OH化合物，产率中等至良好。与以前的研究相比，本研究扩展了底物的范围，并采用了铵盐催化剂（CTAB）和氧化剂（DTBP）的新反应体系。控制和机械实验的结果通常与提出的总体途径一致。该方法可避免使用有毒的P卤素试剂和P（O）-H化合物来合成有机磷化合物。