[7-(1,3-dioxolan-2-yl)-1-heptenyl]-pentamethyl phosphoric triamide | 1251943-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: [7-(1,3-dioxolan-2-yl)-1-heptenyl]-pentamethyl phosphoric triamide
• CAS: 1251943-08-4
• 化学式: C₁₅H₃₂N₃O₃P
• 分子量: 333.411
• InChiKey: MDGPGTJLJDCXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  45.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [7-(1,3-dioxolan-2-yl)-1-heptenyl]-pentamethyl phosphoric triamide 在 硫酸 、 水 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以90%的产率得到7-(1,3-dioxolan-2-yl)heptanal
  参考文献：
  名称：

  Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

  摘要：

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.020
• 作为产物：
  描述：

  N-allyl-N-methyl-(bisdimethylamino) phosphoramide 、 2-(4-iodobutyl)-1,3-dioxolane 在 正丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 以74%的产率得到[7-(1,3-dioxolan-2-yl)-1-heptenyl]-pentamethyl phosphoric triamide
  参考文献：
  名称：

  Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

  摘要：

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.020