1-[氯(乙氧基)磷基]十二烷 | 128894-08-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 1-[氯(乙氧基)磷基]十二烷
• 英文名称: ethyl n-dodecylchlorophoshonate
• 英文别名: Ethyl dodecylphosphonochloridate；1-[chloro(ethoxy)phosphoryl]dodecane
• CAS: 128894-08-6
• 化学式: C₁₄H₃₀ClO₂P
• 分子量: 296.818
• InChiKey: HHMUHUGHBNPMPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[氯(乙氧基)磷基]十二烷 、 4-羟基苯甲腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以83%的产率得到4-Cyanophenyl ethyl dodecylphosphonate
  参考文献：
  名称：

  Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels

  摘要：

  The structure-activity relationships of organophosphorus (OP) and organosulfur compounds were examined in vitro and in vivo as inhibitors of mouse brain monoacylglycerol lipase (MAGL) hydrolysis of 2-arachidonoylglycerol (2-AG) and agonist binding at the CB1 receptor. Several compounds showed exceptional potency toward MAGL activity with IC50 values of 0.1-10 nM in vitro and high inhibition at 10 mg/kg intraperitoneally in mice. We find for the first time that MAGL activity is a major in vivo determinant of 2-AG and arachidonic acid levels not only in brain but also in spleen, lung, and liver. Apparent direct OP inhibition of CB1 agonist binding may be due instead to metabolic stabilization of 2-AG in brain membranes as the actual inhibitor. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.08.007
• 作为产物：
  描述：

  十二烷基膦酸二乙基酯 在 N,N-二甲基甲酰胺 氯化亚砜 作用下， 反应 6.5h， 以31.6%的产率得到dodecylphosphonic dichloride
  参考文献：
  名称：

  Maier, Ludwig, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, p. 465 - 470

  摘要：

  DOI：

文献信息

• [EN] NEW PHOSPHONATE DERIVATIVES AS LIPASE AGENTS INHIBITING
  申请人：NOVO NORDISK A/S

  公开号：WO1992005788A1

  公开（公告）日：1992-04-16

  (EN) Compounds of the formula R-(R2=)P(X)-OR1 wherein R is an optionally substituted alkyl group, R1 is an optionally substituted alkyl group or an optionally substituted phenyl group, R2 is oxygen or sulphur, and X is a leaving group, can be used as lipase inhibiting agents.(FR) On peut utiliser comme agents inhibiteurs de la lipase des composés ayant la formule R-(R2=)P(X)-OR1, dans laquelle R est un groupe alkyle facultativement substitué, R1 est un groupe alkyle facultativement substitué ou un groupe phényle facultativement substitué, R2 désigne l'oxygène ou le soufre, et X est un groupe labile.
• Maier, Ludwig, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, p. 465 - 470
  作者：Maier, Ludwig

  DOI：——

  日期：——
• Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels
  作者：Daniel K. Nomura、Carolyn S.S. Hudak、Anna M. Ward、James J. Burston、Roger S. Issa、Karl J. Fisher、Mary E. Abood、Jenny L. Wiley、Aron H. Lichtman、John E. Casida

  DOI：10.1016/j.bmcl.2008.08.007

  日期：2008.11

  The structure-activity relationships of organophosphorus (OP) and organosulfur compounds were examined in vitro and in vivo as inhibitors of mouse brain monoacylglycerol lipase (MAGL) hydrolysis of 2-arachidonoylglycerol (2-AG) and agonist binding at the CB1 receptor. Several compounds showed exceptional potency toward MAGL activity with IC50 values of 0.1-10 nM in vitro and high inhibition at 10 mg/kg intraperitoneally in mice. We find for the first time that MAGL activity is a major in vivo determinant of 2-AG and arachidonic acid levels not only in brain but also in spleen, lung, and liver. Apparent direct OP inhibition of CB1 agonist binding may be due instead to metabolic stabilization of 2-AG in brain membranes as the actual inhibitor. Published by Elsevier Ltd.