tetra(hexyn-1-yl)tin | 65481-77-8

• 分子结构分类: 有机化合物
• 英文名称: tetra(hexyn-1-yl)tin
• 英文别名: tetra(hex-1-yn-1-yl)tin
• CAS: 65481-77-8
• 化学式: C₂₄H₃₆Sn
• 分子量: 443.26
• InChiKey: XTCFHIGYAGDNEL-UHFFFAOYSA-N

物化性质

• 沸点：
  453.7±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  三乙基硼 、 tetra(hexyn-1-yl)tin 以 甲苯 为溶剂， 以75%的产率得到1,4,6,9-tetrabutyl-3,8-diethyl-2,7-bis(diethylboryl)-5-stannaspiro[4.4]nona-1,3,6,8-tetraene
  参考文献：
  名称：

  Synthesis of 1,6-dihalogeno-2,3,4,5-tetracarba-nido-hexaborane(6) derivatives

  摘要：

  1,4,6,9-Tetraalkyl-3,8-diethyl-2,7-bis(diethylboryl[4.4]mona-1,3,6,8-tetraenes (alkyl = Pt (2a), Pr (2b), Pr-i (2c), ''Bu (2d)) react with four equivalents of boron tribromide to give 2,3,4,5-tetraalkyl-1,6-dibromo-2,3,4,5-tetracarba-nido-hexaboranes(6) (3a-d) in high yield. By monitoring the progress of the reactions using C-13 NMR spectroscopy, 2,5-diboryl-substituted 3-borolenes (10) were identified as intermediates that rearrange to the carboranes via elimination of ethylboron dibromide. Treatment of 2 with boron triiodide affords the analogous 1,6-diodo-substituted carboranes 4. The reaction of 2 with an excess of boron trichloride proceeds rather slowly, again with a 3-borolene (9) as intermediate, and leads finally to a mixture of the carboranes 5 and 6 as a result of elimination of EtBCl(2) or BCl3. Treatment of 2 with BF3 leads to decomposition without any defined products. The carboranes 3 react stepwise with Li[Et(3)BH] to give first the monohydride with a B(6)-H bond (17) and the dihydride with B(6)-H and B(1)-H bonds (18).

  DOI：

  10.1016/0022-328x(95)05619-z
• 作为产物：
  描述：

  四氯化锡 、 1-己炔 在 二乙胺 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以67%的产率得到tetra(hexyn-1-yl)tin
  参考文献：
  名称：

  Stille交叉偶联反应中的四炔基锡烷：芳基炔的新有效途径†

  摘要：

  首次详细研究了与四炔基锡烷的斯蒂勒型交叉偶联反应。该反应提供了通往各种芳基炔烃的简单有效途径。讨论了所提出程序的优点和局限性。

  DOI：

  10.1039/c6nj03905g

文献信息

• Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones
  作者：Andrey S. Levashov、Nicolai A. Aksenov、Inna V. Aksenova、Valeriy V. Konshin

  DOI：10.1039/c7nj01376k

  日期：——

  The reaction of tetraalkynyltin with aldehydes was studied for the first time. The reaction was shown to proceed as a tandem process of nucleophilic addition of tin acetylide to aldehyde followed by Oppenauer-type oxidation of produced tin alcoholates, and may be used as a convenient one-pot approach to acetylenic ketones. The advantages and limitations of the proposed method are discussed.

  首次研究了四炔基锡与醛的反应。该反应显示为乙炔化锡向醛的亲核加成反应，然后对生成的醇锡锡进行Oppenauer型氧化的串联过程，该反应可以用作乙炔酮的便捷一锅法。讨论了该方法的优点和局限性。
• Lewis acid promoted reaction of tetraalkynylstannanes with acyl chlorides: An effective approach towards alkynyl ketones
  作者：Andrey S. Levashov、Dmitrii S. Buryi

  DOI：10.1016/j.tetlet.2017.10.035

  日期：2017.11

  Tetraalkynylstannanes were found to be atom-economical nucleophilic reagents for the synthesis of α,β-acetylenic ketones. The scope and some limitations of the method are discussed.

  发现四炔基锡烷是用于合成α，β-炔酮的原子经济的亲核试剂。讨论了该方法的范围和一些局限性。
• Transmetalation of Tetraalkynyltin Compounds with Grignard Reagents: Access to Mono- and Dialkyltin Products
  作者：Pascale Jaumier、Bernard Jousseaume、Mohammed Lahcini

  DOI：10.1002/(sici)1521-3773(19990201)38:3<402::aid-anie402>3.0.co;2-c

  日期：1999.2.1

  Monoalkyltrialkynyl- and dialkyldialkynyltin compounds can be selectively synthesized by transmetalation of tetraalkynyltin compounds with Grignard reagents; an example is given in Equation (1). This reaction provides a route to mono- and dialkyltin compounds that avoids the use of strongly electrophilic reagents. The labile tin-alkynyl bonds allow the transmetalation products to be converted into alkyltin oxides, chlorides, and alkoxides.
• Wrackmeyer, Bernd; Kehr, Gerald; Boese, Roland, Angewandte Chemie, 1991, vol. 103, p. 1374 - 1376
  作者：Wrackmeyer, Bernd、Kehr, Gerald、Boese, Roland

  DOI：——

  日期：——