(3-oxobutyl)tributylstannane | 98746-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-oxobutyl)tributylstannane
• CAS: 98746-44-2
• 化学式: C₁₆H₃₄OSn
• 分子量: 361.155
• InChiKey: GEPQESNGOKUNJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  363.2±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (3-oxobutyl)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(3-oxobutyl)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-(三丁基锡烷基)丙腈 在 NH₄Cl 作用下， 以 乙醚 、 水 为溶剂， 以59%的产率得到(3-oxobutyl)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

• Stereospecific cyclopropane synthesis from γ-stannyl alcohols
  作者：Ian Fleming、Christopher J. Urch

  DOI：10.1016/0022-328x(85)87366-6

  日期：1985.4
• Nakahira; Ryu; Ogawa, Organometallics, 1990, vol. 9, # 1, p. 277 - 280
  作者：Nakahira、Ryu、Ogawa、Kambe、Sonoda

  DOI：——

  日期：——
• Generation of ketone dilithio α,β-dianions and their reactions with electrophiles
  作者：Hiroyuki Nakahira、Masanobu Ikebe、Yoshiaki Oku、Noboru Sonoda、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1016/j.tet.2005.01.047

  日期：2005.3

  Ketone dilithio alpha,beta- and alpha,beta'-dianions can be generated by a tin-lithium exchange reaction of the lithium enolate of beta-tributyltin substituted ketones. A chelation-aided approach, which employs beta-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone alpha,beta-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles. (c) 2005 Elsevier Ltd. All rights reserved.
• NAKAHIRA, HIROYUKI;RYU, LHYONG;OGAWA, AKIYA;KAMBE, NOBUAKI;SONODA, NOBORU, ORGANOMETALLICS, 9,(1990) N, C. 277-280
  作者：NAKAHIRA, HIROYUKI、RYU, LHYONG、OGAWA, AKIYA、KAMBE, NOBUAKI、SONODA, NOBORU

  DOI：——

  日期：——
• FLEMING, I.;URCH, C. J., J. ORGANOMET. CHEM., 1985, 285, N 1-3, 173-191
  作者：FLEMING, I.、URCH, C. J.

  DOI：——

  日期：——