triisopropyl(ethynyl)germane | 545433-35-0

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: triisopropyl(ethynyl)germane
• 英文别名: triisopropylgermylacetylene；ethynyltriisopropylgermane；i-Pr3Ge(CCH)；ethynyl-tri(propan-2-yl)germane
• CAS: 545433-35-0
• 化学式: C₁₁H₂₂Ge
• 分子量: 226.886
• InChiKey: YWXTXBOKJUSWMY-UHFFFAOYSA-N

物化性质

• 沸点：
  75 °C(Press: 10 Torr)
• 密度：
  0.9659 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  triisopropyl(ethynyl)germane 在 dihydrogen hexachloroplatinate 、 三氯硅烷 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 1.5h， 生成 3,3-diethynyl-6,6-diisopropyl-7-methyl-6-germa-3-silaoct-4-en-1-yne
  参考文献：
  名称：

  多不饱和脂肪族取代基硅烷和锗烷的合成

  摘要：

  炔烃 R3MC≡CH (M = Si, Ge) 的氢化硅烷化得到加合物，其随后用乙炔基溴化镁处理得到多不饱和硅烷和锗烷 R3MCH=CHSi(C≡CH)3。后者可以进行相同的转变以导致不饱和链增长。

  DOI：

  10.1007/s11172-012-0279-z
• 作为产物：
  描述：

  isopropyltrichlorogermane 、 乙炔基溴化镁 以 乙醚 为溶剂， 以85%的产率得到triisopropyl(ethynyl)germane
  参考文献：
  名称：

  摘要：

  The reaction of ethynylmagnesium bromide with chloroisopropylgermanes (i-Pr4-nGeCln, n = 1-3) was used to prepare previously unknown ethynylisopropylgermanes i-Pr4-nGe(C=CH)(n) (n = 1-3). The reaction of Me(3)SiCequivalent toCMgBr with i-PrGeCl3 afforded i-Pr(Me(3)SiCequivalent toC)(3-n)GeCln(n = 1, 2). The reaction of the monochloride with BrMdCequivalent toCH gave i-Pr(HC=C)(2)GeCequivalent toCSiMe(3), while with the dichloride, i-Pr(HCequivalent toC) Ge(Cequivalent toSiMe(3))(2) formed. The latter compounds were obtained by independent synthesis from i-PrGe(Cequivalent toCH)(3), EtMgBr, and ClSiMe3. The reaction of (bromomagnesioethynyl)triisopropylgermane with Me3SiCl gave i-Pr(3)GeCequivalent toSiMe(3).

  DOI：

  10.1023/a:1023450909838

文献信息

• Iridium complex catalyzed germylative coupling reaction between alkynes and iodogermanes – a new route to alkynylgermanium and alkynylgermasilicon compounds
  作者：Monika Rzonsowska、Ireneusz Kownacki、Beata Dudziec、Bogdan Marciniec

  DOI：10.1039/c4dt02290d

  日期：——

  The new reaction of terminal alkynes with iodogermanes proceeding in the presence of an IrI-complex [Ir(μ-Cl)(CO)2}2] (I) and NEt(iPr)2, as a hydrogen iodide acceptor, leads to the formation of functionalized alkynylgermanes. This reaction occurs via direct activation of the Csp–H bond in the starting alkyne. Detailed stoichiometric experiments using [Ir(cod)(CCPh)(PCy3)] (IVa) and iodogermane were

  末端炔烃与碘代锗烷的新反应是在作为碘化氢受体的Ir I-络合物[Ir（μ-Cl）（CO）2 } 2 ]（I）和NEt（i Pr）2的存在下进行的，导致功能化的炔基锗烷的形成。该反应通过起始炔烃中C sp -H键的直接活化而发生。进行了详细的化学计量学实验，使用[Ir（cod）（CCPh）（PCy 3）]（IVa）和碘锗烷，并提出了炔烃和碘锗烷之间生芽偶联反应的合理机理的建议。
• Transition Metal‐Free Catalytic C−H Silylation of Terminal Alkynes with bis(Trimethylsilyl)acetylene Initiated by KHMDS
  作者：Krzysztof Kuciński、Grzegorz Hreczycho

  DOI：10.1002/cctc.202200794

  日期：2022.9.20

  Dealkynative Coupling: C−H silylation of several terminal acetylenes has been established by using sustainable and eco-friendly main-group catalysis. As a result, several alkynes, including pharmaceuticals, were selectively silylated under transition metal-free conditions. Mechanistic studies provided strong support for the deprotonation step, which is followed by the formation of pentacoordinated

  Dealkynative Coupling：通过使用可持续和环保的主基团催化，已经建立了几种末端乙炔的 C-H 硅烷化。结果，包括药物在内的几种炔烃在无过渡金属条件下被选择性甲硅烷基化。机理研究为去质子化步骤提供了强有力的支持，随后形成五配位硅物种。
• Access to Unsaturated Organogermanes via (De)Hydrosilylation Mediated by Cobalt Complexes
  作者：Konstancja Broniarz、Grzegorz Hreczycho

  DOI：10.1021/acs.orglett.3c02326

  日期：2023.9.8

  the reaction can proceed via dehydrogenative coupling or hydrosilylation. Importantly, the presented method is characterized by mild reaction conditions, allowing rapid access to a wide range of organogermanes.

  使用氢硅烷对炔基锗烷进行官能化是通过钴催化完成的。根据所使用的反应物，反应可以通过脱氢偶联或氢化硅烷化进行。重要的是，该方法的特点是反应条件温和，可以快速获得多种有机锗烷。
• A new catalytic route to borylgermyl-substituted buta-1,3-dienes
  作者：Jadwiga Pyziak、Jędrzej Walkowiak、Marcin Hoffmann、Bogdan Marciniec

  DOI：10.1016/j.jorganchem.2015.06.018

  日期：2015.10

  The [Ru(CO)CIH(PCy3)(2)] catalyzed reaction of terminal germyl-substituted alkynes with vinylboronates gives borylgermyl-substituted buta-1,3-dienes as products with high stereo- and regioselectivity. The process that proceeds via direct activation of the C-sp-H bond in the germylalkyne, is a very effective and easy tool for the synthesis of unique borylgermylated alkynes. Eight new compounds were synthesized and fully characterized spectrally. We also determined the mechanism of the process on the basis of stoichiometric reactions, kinetic measurements and DFT calculations. (C) 2015 Elsevier B.V. All rights reserved.