cyclopropylmethyltributylstannane | 81938-26-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: cyclopropylmethyltributylstannane
• 英文别名: tributyl(cyclopropylmethyl)stannane
• CAS: 81938-26-3
• 化学式: C₁₆H₃₄Sn
• 分子量: 345.156
• InChiKey: PZDNSPVKYHSKSC-UHFFFAOYSA-N

物化性质

• 沸点：
  78 °C(Press: 0.07 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  cyclopropylmethyltributylstannane 在 碘 作用下， 以 氘代氯仿 为溶剂， 生成 4-碘-1-丁烯
  参考文献：
  名称：

  The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction.

  摘要：

  The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R = Me) and 1b (R = Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.

  DOI：

  10.1016/s0040-4039(00)74893-3
• 作为产物：
  描述：

  三正丁基氢锡 、 环丙基甲基氯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以37%的产率得到cyclopropylmethyltributylstannane
  参考文献：
  名称：

  Radical Coupling of Iodocarbonyl Compounds with Butenylindium Generated by Transmetalation between Cyclopropylmethylstannane and Indium Halides

  摘要：

  The reaction of cyclopropylmethylstannane 1 with alpha-iodocarbonyl compounds 2 in the presence of either InBr3 or InCl3 gave the C-C coupling products 3. Various types of iodocarbonyl compounds such as esters, amides, and ketones were applied to this system to afford the corresponding cyclopropylethylsubstituted carbonyls 3. Transmetalation between cyclopropylmethylstannane and indium halides afforded butenylindium dihalide and dibutenylindium halide, as confirmed by NMR spectroscopy. The reactivity of dibutenylindium halide was greater than that of monobutenyl species. The active species, dibutenylindium halide, was stabilized by complexation using DPPE, and its structure was analyzed using X-ray crystallography. The solid state of the complex shows a linear structure with a core (-Cl-In-Cl-In-P-C-C-P-In-),, with five-coordinated indium centers. The reaction between I and 2, mediated by indium halides, proceeded in a radical manner. The in situ-generated alkylindium species and a small amount of oxygen, which can be supplied by atmospheric air, initiated the radical reaction.

  DOI：

  10.1021/om8009156

文献信息

• Synthesis of Cyclopropane-Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds
  作者：Kensuke Kiyokawa、Itaru Suzuki、Makoto Yasuda、Akio Baba

  DOI：10.1002/ejoc.201001471

  日期：2011.4

  by-product to be inert to the reaction system. In addition, the transmetalation of a (cyclopropylmethyl)stannane and InBr3 provided the dibutenylindium bromide as a single product, which smoothly coupled with the unstable phosphonyl radical species from the iodo phosphorus compound. A photochemical method (UV irradiation) was also applied and accelerated the coupling reaction. The cyclopropylmethylated

  通过（环丙基甲基）锡烷和 InBr3 之间的金属转移反应制备的 α-或 β-碘代磷化合物（如碘膦酸酯、碘代膦氧化物和碘代硫代膦酸酯）与丁烯基的自由基偶联，得到相应的环丙基甲基化产物。自由基反应是由丁烯基铟产生的自由基物种在少量氧气的辅助下引发的。Butenylindium 不仅可用作环丙基甲基化试剂，还可用作自由基引发剂。为了成功偶联，使用了锡/铟金属转移，其中卤化锡副产物对反应系统呈惰性非常重要。此外，（环丙基甲基）锡烷和 InBr3 的金属转移提供了二丁烯基溴化铟作为单一产品，其与来自碘磷化合物的不稳定膦酰基物种顺利偶联。还应用了光化学方法（紫外线照射）并加速了偶联反应。产生的环丙基甲基化膦酸酯是 Horner-Wadsworth-Emmons 反应的良好中间体，并产生带有环丙烷部分的官能化烯烃。
• Substituted Butenylindium Generated by Transmetalation of Cyclopropylmethylstannane with Indium Iodide: Synthesis and Characterization of Monobutenylindium
  作者：Kensuke Kiyokawa、Makoto Yasuda、Akio Baba

  DOI：10.1021/om200094m

  日期：2011.4.11

  dibutenylindium species. The bulky substituent on a cyclopropyl ring selectively afforded the monobutenylindium species, which allowed the isolation and X-ray structural analysis of the monobutenylindium complex. In an investigation of the generated substituted butenylindium species, we found that indium halide interacted with the less sterically hindered carbon−carbon bond of the cyclopropyl ring during transmetalation

  取代的环丙基甲基锡与碘化铟之间的金属转移提供了相应的单丁烯基和二丁烯基铟。环丙基环上的庞大取代基选择性提供了单丁烯基铟物种，从而可以对单丁烯基铟络合物进行分离和X射线结构分析。在对生成的取代丁烯铟物种的研究中，我们发现卤化铟在金属转移过程中与环丙基环的空间位阻较小的碳-碳键相互作用。另外，我们检查了取代的丁烯铟物种与α-碘酸酯的自由基偶联反应。环丙基甲基化和烯烃产物的分布证明了反应受到丁烯基铟物种取代基的空间效应的显着影响，
• Radical Coupling of Iodocarbonyl Compounds with Butenylindium Generated by Transmetalation between Cyclopropylmethylstannane and Indium Halides
  作者：Makoto Yasuda、Kensuke Kiyokawa、Kenji Osaki、Akio Baba

  DOI：10.1021/om8009156

  日期：2009.1.12

  The reaction of cyclopropylmethylstannane 1 with alpha-iodocarbonyl compounds 2 in the presence of either InBr3 or InCl3 gave the C-C coupling products 3. Various types of iodocarbonyl compounds such as esters, amides, and ketones were applied to this system to afford the corresponding cyclopropylethylsubstituted carbonyls 3. Transmetalation between cyclopropylmethylstannane and indium halides afforded butenylindium dihalide and dibutenylindium halide, as confirmed by NMR spectroscopy. The reactivity of dibutenylindium halide was greater than that of monobutenyl species. The active species, dibutenylindium halide, was stabilized by complexation using DPPE, and its structure was analyzed using X-ray crystallography. The solid state of the complex shows a linear structure with a core (-Cl-In-Cl-In-P-C-C-P-In-),, with five-coordinated indium centers. The reaction between I and 2, mediated by indium halides, proceeded in a radical manner. The in situ-generated alkylindium species and a small amount of oxygen, which can be supplied by atmospheric air, initiated the radical reaction.
• The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction.
  作者：Andrew J Lucke、David J Young

  DOI：10.1016/s0040-4039(00)74893-3

  日期：1991.2

  The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R = Me) and 1b (R = Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.