diethyl 2,2-bis(3-iodopropyl)malonate | 163012-41-7

• 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: diethyl 2,2-bis(3-iodopropyl)malonate
• CAS: 163012-41-7
• 化学式: C₁₃H₂₂I₂O₄
• 分子量: 496.124
• InChiKey: DOURZWFVHWDIPK-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±42.0 °C(Predicted)
• 密度：
  1.723±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  19.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diethyl 2,2-bis(3-iodopropyl)malonate 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到Ethyl cis-5-hydroxybicyclo<3.3.0>octane-1-carboxylate
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Tandem Intramolecular Nucleophilic Acyl Substitution/Intramolecular Barbier Cyclizations

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion-cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.

  DOI：

  10.1021/ja00118a007
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 bis(cyclohexanyl)borane 、 sodium acetate 、 一氯化碘 、 sodium hydride 作用下， 反应 5.5h， 生成 diethyl 2,2-bis(3-iodopropyl)malonate
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Tandem Intramolecular Nucleophilic Acyl Substitution/Intramolecular Barbier Cyclizations

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion-cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.

  DOI：

  10.1021/ja00118a007