三甲基(辛-1-炔基)锡烷 | 109059-09-8

• 分子结构分类: 有机化合物 - 乙炔化物 - 金属乙炔化物
• 中文名称: 三甲基(辛-1-炔基)锡烷
• 英文名称: 1-trimethylstannyloct-1-yne
• 英文别名: tribmethyl(1-octynyl)tin；trimethyl(oct-1-ynyl)stannane；Trimethyl(oct-1-YN-1-YL)stannane
• CAS: 109059-09-8
• 化学式: C₁₁H₂₂Sn
• 分子量: 273.006
• InChiKey: WLACNHTWYONPKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  bis(cyclohexanyl)borane 、 三甲基(辛-1-炔基)锡烷 以 not given 为溶剂， 生成 1-dicyclohexylboranyloct-1-enyl(trimethyl)stannane
  参考文献：
  名称：

  Pelter, Andrew; Smith, Keith; Jones, Kevin, Pure and Applied Chemistry, 1991, vol. 63, p. 403 - 406

  摘要：

  DOI：
• 作为产物：
  描述：

  1-辛炔 、 三甲基氯化锡 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 三甲基(辛-1-炔基)锡烷
  参考文献：
  名称：

  Pelter, Andrew; Smith, Keith; Parry, David E., Australian Journal of Chemistry, 1992, vol. 45, # 1, p. 57 - 70

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Addition of Terminal Alkynes to Alkynylstannanes with Migration of the Stannyl Group
  作者：Eiji Shirakawa、Kouji Nakayama、Ryotaro Morita、Teruhisa Tsuchimoto、Yusuke Kawakami、Toshiaki Matsubara

  DOI：10.1246/bcsj.79.1963

  日期：2006.12

  In the presence of a catalytic amount of a ruthenium complex coordinated with PBu3, alkynylstannanes (R1C≡CSnBu3) were found to accept the addition of terminal alkynes (R2C≡CH) with a 1,2-shift of the stannyl group to give (E)- and (Z)-1-tributylstannylbut-1-en-3-ynes (Bu3SnC(R1)=CHC≡CR2). Various combinations of substrates having an aromatic and/or aliphatic substituent can be used, and the stereochemical outcome depends largely on the character of these substituents. The reaction of aliphatic terminal alkynes proceeds stereoselectively, and substituent R1 on the alkynylstannanes determines the configuration: E for R1 = alkyl and Z for R1 = aryl. In contrast, the reaction of arylacetylenes gave a mixture of stereoisomers irrespective of the character of substituent R1 on the alkynylstannane. Ruthenium–β-stannylvinylidene complexes generated from a ruthenium complex and an alkynylstannane with migration of the stannyl group are likely to be key intermediates, which accept addition of the C–H bond of terminal alkynes to give the corresponding stannylenynes. DFT calculation clearly shows that the 1,2-shift of the stannyl group on formation of ruthenium–β-stannylvinylidene complexes is more facile than the corresponding 1,2-hydrogen shift of the coordinating terminal alkynes. The effect of the substituents on the stereoselectivity also is discussed based on the calculation.

  在以PBu3配位的钌络合物的催化作用下，炔基锡烷（R1C≡CSnBu3）可以接受端炔（R2C≡CH）的加成，伴随锡基团的1,2-迁移，生成(E)-和(Z)-1-三丁基锡基丁-1-烯-3-炔（Bu3SnC(R1)=CHC≡CR2）。可以使用具有芳香和/或脂肪族取代基的各种底物组合，立体化学结果主要取决于这些取代基的性质。脂肪族端炔的反应具有立体选择性，且炔基锡烷上的取代基R1决定构型：R1为烷基时得到E构型，R1为芳基时得到Z构型。相比之下，芳基乙炔的反应产生立体异构体的混合物，与炔基锡烷上取代基R1的性质无关。由钌络合物和炔基锡烷经锡基团迁移生成的钌-β-锡基亚甲基络合物可能是关键中间体，它们接受端炔的C-H键加成生成相应的锡基烯炔。DFT计算清楚地表明，在形成钌-β-锡基亚甲基络合物时，锡基团的1,2-迁移比配位端炔的相应1,2-氢迁移更容易进行。文中还基于计算讨论了取代基对立体选择性的影响。
• ‘Alk-l-ynyllead triacetates’ as alk-1-ynyl carbocation equivalents. The α-alk-1-ynylation of β-dicarbonyl compounds and nitronate salts
  作者：Mark G. Moloney、John T. Pinhey、Eric G. Roche

  DOI：10.1016/s0040-4039(00)85124-2

  日期：1986.1

  alk-l-ynyltrimethylstannane results in the rapid formation of trimethylstannyl acetate and an unstable species, believed to be the corresponding alk-l-ynyllead triacetate, which can effect the rapid α-alkynylation of β-dicarbonyl compounds and nitronate salts.

  将四乙酸铅添加到烷基-1-炔基三甲基锡烷的氯仿溶液中会迅速形成乙酸三甲基锡烷基酯和不稳定的物质，据信是相应的烷基-1-炔基三乙酸铅，可导致β的快速α-炔基化-二羰基化合物和硝酸盐。
• A facile preparation of 1-perflouroalkylalkenes and alkynes. Palladium catalyzed reaction of perfluoroalkyl iodides with organotin compounds
  作者：Seijiro Matsubara、Makoto Mitani、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(01)81073-x

  日期：1987.1

  Alkenyl, allyl, and alkynylstannanes react with perfluoroalkyl iodides in the presence of a catalytic amount of Pd(PPh3)4 to give alkenes and alkynes bearing perfluoroalkyl group.

  在催化量的Pd（PPh 3）4存在下，烯基，烯丙基和炔基锡烷与全氟烷基碘反应，得到带有全氟烷基的烯烃和炔烃。
• Moloney, Mark G.; Pinhey, John T.; Roche, Eric G., Journal of the Chemical Society. Perkin transactions I
  作者：Moloney, Mark G.、Pinhey, John T.、Roche, Eric G.

  DOI：——

  日期：——
• Pelter, Andrew; Smith, Keith; Jones, Kevin D., Journal of the Chemical Society. Perkin transactions I, 1992, # 7, p. 747 - 748
  作者：Pelter, Andrew、Smith, Keith、Jones, Kevin D.

  DOI：——

  日期：——