tributyl[2-(2-pyridyl)ethyl]stannane | 195876-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tributyl[2-(2-pyridyl)ethyl]stannane
• 英文别名: [2-(2-pyridyl)ethyl]tributyltin；[2-(2-pyridyl)ethyl]tributylstannane
• CAS: 195876-17-6
• 化学式: C₁₉H₃₅NSn
• 分子量: 396.204
• InChiKey: ZOTOXPDOGGUPEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tributyl[2-(2-pyridyl)ethyl]stannane 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三(五氟苯基)膦 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 dimethyl [(E)-5-(2-pyridyl)-2-penten-1-yl]malonate
  参考文献：
  名称：

  可去除2-PyMe2Si基团指导的区域选择性催化烯丙基烷基化

  摘要：

  一般实验。NMR 光谱记录在 Varian GEMINI-2000 (1H 300 MHz, 13C 75 MHz) 和 JEOL A-500 (1H 500 MHz, 13C 125 MHz) 光谱仪上，在 CDCl3 中使用内标 (7.26 ppm 1H, 77.0 ppm 13C)。EI 质谱记录在 JMS-SX102A 光谱仪上。FAB 质谱记录在 JMS-HX110A 光谱仪上。在 Shimadzu FTIR-8100 分光光度计上记录红外光谱。凝胶渗透色谱采用日本分析工业 LC-918 进行。除非另有说明，所有材料均从商业供应商处获得，无需进一步纯化即可使用。在使用前，二乙醚 (Et2O) 和四氢呋喃 (THF) 在氩气下从二苯甲酮酮基钠中新鲜蒸馏。根据文献程序制备2-吡啶基三甲基硅烷。

  DOI：

  10.1021/ja0157346
• 作为产物：
  描述：

  2-乙烯基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 以63%的产率得到tributyl[2-(2-pyridyl)ethyl]stannane
  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 from Heteroatom Compounds. Electrochemical Oxidation of 2-(2-Pyridyl)ethyl-Substituted Ethers, Sulfides, and Selenides
  作者：Mitsuru Watanabe、Seiji Suga、Jun-ichi Yoshida

  DOI：10.1246/bcsj.73.243

  日期：2000.1

  Organoheteroatom compounds having a 2-(2-pyridyl)ethyl group were synthesized and their oxidation potentials were determined by rotating disk electrode voltammetry. The oxidation potentials were found to be less positive than those of the corresponding compounds having a phenyl group in place of the pyridyl group. The dynamic coordination of the pyridyl group to the heteroatom, which stabilizes the

  合成了具有 2-(2-吡啶基)乙基的有机杂原子化合物，并通过旋转圆盘电极伏安法测定了它们的氧化电位。发现氧化电位低于具有苯基代替吡啶基的相应化合物的氧化电位。吡啶基与杂原子的动态配位稳定了阳离子自由基中间体，似乎是促进电子转移的原因。分子内辅助的量级随着母体化合物氧化电位的增加而增加。这种趋势可以用吡啶氮的非键合 p 轨道和母体杂原子化合物的 HOMO 之间的能量匹配来解释。
• 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.
• Regioselective Catalytic Allylic Alkylation Directed by Removable 2-PyMe₂Si Group
  作者：Kenichiro Itami、Tooru Koike、Jun-ichi Yoshida

  DOI：10.1021/ja0157346

  日期：2001.7.1

  materials were obtained from commercial suppliers and used without further purification. Diethyl ether (Et2O) and tetrahydrofuran (THF) were freshly distilled under argon from sodium benzophenone ketyl prior to use. 2-Pyridyltrimethylsilane was prepared according to the literature procedures.1 [2-(2-Pyridyl)ethyl]tributyltin was prepared according to the literature procedures.2

  一般实验。NMR 光谱记录在 Varian GEMINI-2000 (1H 300 MHz, 13C 75 MHz) 和 JEOL A-500 (1H 500 MHz, 13C 125 MHz) 光谱仪上，在 CDCl3 中使用内标 (7.26 ppm 1H, 77.0 ppm 13C)。EI 质谱记录在 JMS-SX102A 光谱仪上。FAB 质谱记录在 JMS-HX110A 光谱仪上。在 Shimadzu FTIR-8100 分光光度计上记录红外光谱。凝胶渗透色谱采用日本分析工业 LC-918 进行。除非另有说明，所有材料均从商业供应商处获得，无需进一步纯化即可使用。在使用前，二乙醚 (Et2O) 和四氢呋喃 (THF) 在氩气下从二苯甲酮酮基钠中新鲜蒸馏。根据文献程序制备2-吡啶基三甲基硅烷。