(4-oxopentyl)tributylstannane | 195876-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-oxopentyl)tributylstannane
• CAS: 195876-24-5
• 化学式: C₁₇H₃₆OSn
• 分子量: 375.182
• InChiKey: NYZLHPKHGYIUDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-oxopentyl)tributylstannane 、 sodium chloride 在 2,6-lutidine 、 Bu₄NClO₄ 、 molecular sieve 4A 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 chloro(4-oxopentyl)dibutylstannane
  参考文献：
  名称：

  Intramolecular Assistance of Electron Transfer. Oxidative Cleavage of the Carbon−Tin Bond of Tetraalkylstannanes

  摘要：

  Experimental and theoretical studies of intramolecular assistance by carbonyl groups and heteroatoms in the electron transfer driven cleavage of the carbon-tin bond of tetraalkylstannanes has been carried out. Carbonyl groups and heteroatoms (oxygen and nitrogen) in an appropriate position of tetraalkylstannane facilitate the electron transfer and selective cleavage of the carbon-tin bond. Although the coordination of the carbonyl groups and heteroatoms to tin was not detected in the neutral molecules, molecular orbital calculations indicate that the coordination of such groups to tin in the cation radical intermediate stabilizes the system and weakens the carbon-tin bond. These results offer striking examples of the intramolecular assistance of electron transfer driven reactions.

  DOI：

  10.1021/ja970899t
• 作为产物：
  描述：

  甲基碘化镁 、 (3-氰基丙基)三丁基锡烷 在 NH₄Cl 作用下， 以 乙醚 、 水 为溶剂， 以55%的产率得到(4-oxopentyl)tributylstannane
  参考文献：
  名称：

  Intramolecular Assistance of Electron Transfer. Oxidative Cleavage of the Carbon−Tin Bond of Tetraalkylstannanes

  摘要：

  Experimental and theoretical studies of intramolecular assistance by carbonyl groups and heteroatoms in the electron transfer driven cleavage of the carbon-tin bond of tetraalkylstannanes has been carried out. Carbonyl groups and heteroatoms (oxygen and nitrogen) in an appropriate position of tetraalkylstannane facilitate the electron transfer and selective cleavage of the carbon-tin bond. Although the coordination of the carbonyl groups and heteroatoms to tin was not detected in the neutral molecules, molecular orbital calculations indicate that the coordination of such groups to tin in the cation radical intermediate stabilizes the system and weakens the carbon-tin bond. These results offer striking examples of the intramolecular assistance of electron transfer driven reactions.

  DOI：

  10.1021/ja970899t

文献信息

• Intramolecular Assistance of Electron Transfer. Oxidative Cleavage of the Carbon−Tin Bond of Tetraalkylstannanes
  作者：Jun-ichi Yoshida、Mitsuhiko Izawa

  DOI：10.1021/ja970899t

  日期：1997.10.1

  Experimental and theoretical studies of intramolecular assistance by carbonyl groups and heteroatoms in the electron transfer driven cleavage of the carbon-tin bond of tetraalkylstannanes has been carried out. Carbonyl groups and heteroatoms (oxygen and nitrogen) in an appropriate position of tetraalkylstannane facilitate the electron transfer and selective cleavage of the carbon-tin bond. Although the coordination of the carbonyl groups and heteroatoms to tin was not detected in the neutral molecules, molecular orbital calculations indicate that the coordination of such groups to tin in the cation radical intermediate stabilizes the system and weakens the carbon-tin bond. These results offer striking examples of the intramolecular assistance of electron transfer driven reactions.