2-tributylstannyl-1,3-dioxolane | 118418-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-tributylstannyl-1,3-dioxolane
• 英文别名: tributyl(1,3-dioxolan-2-yl)stannane
• CAS: 118418-21-6
• 化学式: C₁₅H₃₂O₂Sn
• 分子量: 363.128
• InChiKey: PWPIUKSUXKFJGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 2-tributylstannyl-1,3-dioxolane 在 正丁基锂 作用下， 生成 (1,3-dioxolan-2-yl)-tert-butyldimethylsilane
  参考文献：
  名称：

  Formylsilanes. Chemoenzymic and chemical synthesis of the 2,4-dinitrophenylhydrazones of these apparently air- and water-stable compounds

  摘要：

  Formylsilanes have long been reported to be notoriously unstable compounds. In fact, no formylsilane has been reported that was stable in air or in water nor are there any known hydrates, imines, or hydrazones of formylsilanes. We have found that monoamine oxidase catalyzes the oxidation of (aminomethyl)-tert-butyl-dimethylsilane in aqueous buffer at pH 9 to give, apparently, either formyl-tert-butyldimethylsilane or the corresponding hydrate, which is isolated as the 2,4-dinitrophenylhydrazone. The chemical synthesis of this same compound and the corresponding formyltrimethylsilane was carried out in low yields by a standard route to acylsilanes but in good yields by a new route involving conversion of (1,3-dioxolan-2-yl)tri-n-butylstannane to the corresponding silanes followed by acid hydrolysis. Although the formylsilane could not be isolated, it or its hydrate apparently is stable enough in water to survive incubation for several hours prior to the 2,4-dinitrophenylhydrazine trapping reaction.

  DOI：

  10.1021/jo00050a046
• 作为产物：
  描述：

  乙二醇 、 diethoxymethyltributyltin 在 catalyst: p-toluenesulfonic acid 作用下， 以 苯 为溶剂， 以72%的产率得到2-tributylstannyl-1,3-dioxolane
  参考文献：
  名称：

  α-三丁基锡缩醛：通过乙二氧基甲基三丁基锡的反缩醛化制备，并用于合成新的α-锡烷基化醚

  摘要：

  容易获得的二乙氧基甲基三丁基锡的反缩醛化反应可提供多种新的α-锡烷基缩醛，当它们含有不稳定或手性烷氧基时，有望具有较高的选择性有机合成潜力。通过用有机铝卤化物处理或通过使用乙酰氯/格氏试剂序列，可以将α-锡烷基缩醛转化为相应的取代的α-锡烷基醚。该研究集中于烯丙基，均烯丙基和均炔丙基衍生物，它们提供了有机合成的最佳潜力。

  DOI：

  10.1016/0022-328x(90)80020-z

文献信息

• Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals
  作者：Isabelle Beaudet、Alain Duchêne、Jean-Luc Parrain、Jean-Paul Quintard

  DOI：10.1016/0022-328x(92)83085-v

  日期：1992.4

  The substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents has been examined in a search for new methods of preparing functional acetals. The efficiency of the substitution of the acetoxy group is highly dependent on the nature of the organometallic reagents: soft nucleophiles with strong electrophilic assistance by the counterion are the best reagents. Allyl-, propargyl-

  为了寻找制备功能性乙缩醛的新方法，已经研究了用有机金属试剂取代二烷氧基甲基乙酸酯的乙酰氧基。乙酰氧基的取代效率高度依赖于有机金属试剂的性质：具有抗衡离子的强亲电助剂的柔软亲核试剂是最好的试剂。通过这种途径制备了烯丙基，炔丙基，高烯丙基，高炔丙基和α-锡烷基缩醛，其中二烷氧基甲基乙酸酯经常用作二烷基苯基原甲酸酯的有用替代物。
• Stereospecific Cyclopropanation Reactions of Stannyl-Substituted Acetals with Alkenes via <i>γ</i>-Elimination of Tin
  作者：Masanobu Sugawara、Jun-ichi Yoshida

  DOI：10.1055/s-1998-1896

  日期：1998.10

  The reactions of stannyl substituted acetals with olefins resulted in the elimination of both the triorganostannyl group and the alkoxy group on the same carbon, and the production of the corresponding alkoxycyclopropanes in good yields. The stereospecificity of the present reaction suggests that γ-elimination of tin is very fast.

  锡取代的乙醛与烯烃反应后，同一碳上的三有机锡基和烷氧基均被消除，并以良好的收率生成相应的烷氧基环丙烷。本反应的立体特异性表明，δ-消除锡的速度非常快。
• SHINER, CHRISTOPHER S.;TSUNODA, TETSUTO;GOODMAN, BURTON A.;INGHAM, STEPHE+, J. AMER. CHEM. SOC., 111,(1989) N, C. 1381-1392
  作者：SHINER, CHRISTOPHER S.、TSUNODA, TETSUTO、GOODMAN, BURTON A.、INGHAM, STEPHE+

  DOI：——

  日期：——
• DUCHENE, ALAIN;BOISSIERE, SOPHIE;PARRAIN, JEAN-LUC;QUINTARD, JEAN-PAUL, J. ORGANOMET. CHEM., 387,(1990) N, C. 153-162
  作者：DUCHENE, ALAIN、BOISSIERE, SOPHIE、PARRAIN, JEAN-LUC、QUINTARD, JEAN-PAUL

  DOI：——

  日期：——
• α-tributylstannylacetals: Preparation via transacetalisation of diethoxymethyltributyltin, and use for the synthesis of new α-stannylated ethers
  作者：Alain Duchêne、Sophie Boissière、Jean-Luc Parrain、Jean-Paul Quintard

  DOI：10.1016/0022-328x(90)80020-z

  日期：1990.5

  diethoxymethyltributyltin affords a large variety of new α-stannylacetals, which are expected to have a high potential for selective organic synthesis when they contain labile or chiral alkoxy groups. The α-stannylacetals can be converted into the corresponding substituted α-stannyl-ethers by treatment with organoaluminium halides or by use of an acetyl chloride/Grignard reagent sequence. The study has concentrated

  容易获得的二乙氧基甲基三丁基锡的反缩醛化反应可提供多种新的α-锡烷基缩醛，当它们含有不稳定或手性烷氧基时，有望具有较高的选择性有机合成潜力。通过用有机铝卤化物处理或通过使用乙酰氯/格氏试剂序列，可以将α-锡烷基缩醛转化为相应的取代的α-锡烷基醚。该研究集中于烯丙基，均烯丙基和均炔丙基衍生物，它们提供了有机合成的最佳潜力。