diethyl (2RS,6SR)-4-benzyloxy-2,6-dimethyleneheptanedioate | 950916-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl (2RS,6SR)-4-benzyloxy-2,6-dimethyleneheptanedioate
• 英文别名: diethyl (2R,6S)-2,6-dihexyl-4-phenylmethoxyheptanedioate
• CAS: 950916-84-4
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: OQSBXOMHOIYLSM-FITHBNAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (2RS,6SR)-4-benzyloxy-2,6-dimethyleneheptanedioate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到(2RS,6SR)-4-benzyloxy-2,6-dimethyleneheptane-1,7-diol
  参考文献：
  名称：

  Radical mediated stereoselective synthesis of meso-7,11-dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper

  摘要：

  meso-7,11-Dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper, was synthesized from ethyl 2-(bromomethyl) propenoate in nine steps and 14% overall yield. The key step in the synthesis is the highly diastereo-selective chelation-controlled radical reaction of diethyl 4-benzyloxy-2,6-dimethyleneheptanedioate with pentyl iodide performed in the presence of 6 equiv of MgBr2 center dot OEt2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.027
• 作为产物：
  描述：

  ethyl 2-(2-hydroxyethyl)propenoate 在 三乙基硼 、 三氟甲磺酸 、 三正丁基氢锡 、 sodium acetate 、 氯化铵 、 pyridinium chlorochromate 、 magnesium bromide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 29.0h， 生成 diethyl (2RS,6SR)-4-benzyloxy-2,6-dimethyleneheptanedioate
  参考文献：
  名称：

  Radical mediated stereoselective synthesis of meso-7,11-dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper

  摘要：

  meso-7,11-Dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper, was synthesized from ethyl 2-(bromomethyl) propenoate in nine steps and 14% overall yield. The key step in the synthesis is the highly diastereo-selective chelation-controlled radical reaction of diethyl 4-benzyloxy-2,6-dimethyleneheptanedioate with pentyl iodide performed in the presence of 6 equiv of MgBr2 center dot OEt2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.027