S-(4-(1,3-dioxoisoindolin-2-yl)butyl)O,O-diethyl phosphorothioate | 1347618-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: S-(4-(1,3-dioxoisoindolin-2-yl)butyl)O,O-diethyl phosphorothioate
• 英文别名: 2-(4-Diethoxyphosphorylsulfanylbutyl)isoindole-1,3-dione；2-(4-diethoxyphosphorylsulfanylbutyl)isoindole-1,3-dione
• CAS: 1347618-12-5
• 化学式: C₁₆H₂₂NO₅PS
• 分子量: 371.394
• InChiKey: ZCPLATPMENEVQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  potassium O,O'-diethylthiophosphate 、 N-(4-溴丁基)邻苯二甲酰亚胺 以 乙醇 为溶剂， 反应 12.0h， 以42%的产率得到S-(4-(1,3-dioxoisoindolin-2-yl)butyl)O,O-diethyl phosphorothioate
  参考文献：
  名称：

  Homo- and hetero-dimers of inactive organophosphorous group binding at dual sites of AChE

  摘要：

  Homo- and hetero-dimers of inactive organophosphorous group(s) dramatically enhanced the acetylcholinesterase (AChE; EC 3.1.1.7) inhibiting potency, with the highest potency observed at a tether length of 6 methylene groups (6d) for the homodimers, and 7 methylene groups (8e) for the heterodimers. The docking model of Drosophila melanogaster AChE suggested that 6d and 8e bound at the catalytic and peripheral sites of AChE, in which two organophosphorous groups of 6d individually oriented towards TRP83 of catalytic sites and TRP321 of peripheral sites, and phthalicimide group of 8e was appropriately arranged for a pi-pi interaction with the phenyl ring of TYR330, furthermore, the organophosphorous group introduced hydrophobic interaction with TRP83. The compounds prepared in this work demonstrated high insecticidal activity to Lipaphis erysimi and Tetranychus cinnbarinus at the concentration 300 mg/L. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.098

文献信息

• Three-Component Coupling Reaction in Water: A One-Pot Protocol for the Construction of P-S-C(sp³ ) and P-Se-C(sp³ ) Bonds
  作者：Xinghua Zhang、Zheng Shi、Changwei Shao、Jinlong Zhao、Dungai Wang、Gaoqi Zhang、Liang Li

  DOI：10.1002/ejoc.201700344

  日期：2017.4.10

  A one-pot, three-component coupling reaction of primary alkyl halides (or tosylates), elemental sulfur/selenium, and P(O)–H compounds in water was developed. This procedure affords valuable phosphorothioates/phosphoroselenoates, including P-chiral compounds, with broad substrate scope and high efficiency. Moreover, this facile protocol can be applied to gram-scale preparations.

  开发了伯烷基卤化物（或甲苯磺酸盐）、元素硫/硒和 P(O)–H 化合物在水中的一锅三组分偶联反应。该过程提供了有价值的硫代磷酸酯/硒代磷酸酯，包括 P-手性化合物，具有广泛的底物范围和高效率。此外，这种简便的协议可以应用于克级制剂。