(E)-8-(2-methyl-1,3-dioxolan-2-yl)oct-2-enoic acid | 190520-32-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-8-(2-methyl-1,3-dioxolan-2-yl)oct-2-enoic acid
• CAS: 190520-32-2
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: SAYYSCJNBCWJMQ-FNORWQNLSA-N

物化性质

• 沸点：
  356.0±17.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-8-(2-methyl-1,3-dioxolan-2-yl)oct-2-enoic acid 在 盐酸 、 水 作用下， 反应 4.0h， 生成 9-氧代-2-癸烯酸
  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：

  二乙基磷乙酸 、 6-(2-methyl-1,3-dioxolan-2-yl)-hexanal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以91%的产率得到(E)-8-(2-methyl-1,3-dioxolan-2-yl)oct-2-enoic acid
  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

文献信息

• 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
  作者：Tomasz K. Olszewski、Catherine Bomont、Philippe Coutrot、Claude Grison

  DOI：10.1016/j.jorganchem.2010.06.020

  日期：2010.10

  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.