2-methyl-2-((trimethylsilyl)oxy)nonanenitrile | 65790-43-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-methyl-2-((trimethylsilyl)oxy)nonanenitrile
• 英文别名: 2-Methyl-2-trimethylsilyloxynonanitril；2-Methyl-2-trimethylsilyloxynonanenitrile
• CAS: 65790-43-4
• 化学式: C₁₃H₂₇NOSi
• 分子量: 241.449
• InChiKey: DIVQVHMTSAJKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  280.0±23.0 °C(Predicted)
• 密度：
  0.866±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 2-壬酮 在 polystyrene-supported triphenylphosphine 作用下， 以 neat (no solvent) 为溶剂， 反应 4.5h， 生成 2-methyl-2-((trimethylsilyl)oxy)nonanenitrile
  参考文献：
  名称：

  通过1,2-化学选择性高效合成氰醇三甲基甲硅烷基醚氰基硅烷化 羰基

  摘要：

  在这里，我们报告了一种可持续的协议，用于 羰基化合物 1a–g和3a–m使用三甲基甲硅烷基氰化物 和 三苯膦 支撑在聚苯乙烯上 催化剂 在下面 溶剂无条件。已经表明，少量的催化剂 允许化学选择性1,2-加成 三甲基甲硅烷基氰化物α，β-不饱和羰基1a–g（5 mol％）和饱和羰基3a–m（2 mol％）。氰醇三甲基甲硅烷基醚2a–g和4a–m的制备以良好的收率（72–99％）和非常低的E因子值（5–10）完成。最后，通过设置两种不同的流程进一步提高了效率，这使我们能够大规模进行氰醇三甲基甲硅烷基醚4a的代表性制备，E因子为0.16或0.47，减少了90％或72％与我们的批次条件相比

  DOI：

  10.1039/c2gc36442e

文献信息

• <i>n</i>-Butyllithium as a highly efficient precatalyst for cyanosilylation of aldehydes and ketones
  作者：Zihan Kang、Xiaojuan Xu、Yuhong Wang、Wenxuan Zhang、Shuai Zhou、Xu Zhu、Mingqiang Xue

  DOI：10.1039/d1ob01297e

  日期：——

  A highly efficient cyanosilylation protocol mediated by the easily available n-BuLi with a wide range of aldehydes and ketones was developed. This protocol features excellent yields with very low n-BuLi loadings (0.01–0.05 mol%) at room temperature, solvent-free process, good chemo-/regio-selectivity and functional group tolerance and scalability. A possible reaction pathway based upon stoichiometric

  开发了一种由易于获得的正丁基锂和多种醛和酮介导的高效氰基化方案。该协议的特点是在室温下具有极低的n- BuLi 负载 (0.01–0.05 mol%)、无溶剂工艺、良好的化学/区域选择性和官能团耐受性和可扩展性，具有出色的收率。提出了一种基于化学计量反应性的可能反应途径。
• Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene
  作者：Taichi Kano、Kouji Sasaki、Teppei Konishi、Haruka Mii、Keiji Maruoka

  DOI：10.1016/j.tetlet.2006.04.141

  日期：2006.7

  The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields.

  N-杂环卡宾的合成用途通过醛，酮和亚胺的三烷基甲硅烷基氰化来证明。在催化量3a的存在下，与Me 3 SiCN的反应平稳进行，以良好的产率获得了相应的氰醇三甲基甲硅烷基醚或氨基腈衍生物。
• The application of spontaneous flocculation for the preparation of lanthanide-containing polyoxometalates intercalated layered double hydroxides: highly efficient heterogeneous catalysts for cyanosilylation
  作者：Yueqing Jia、Shen Zhao、Yu-Fei Song

  DOI：10.1016/j.apcata.2014.09.005

  日期：2014.10

  The lanthanide-containing polyoxometalates (POMs) have been intercalated into layered double hydroxides (LDHs) successfully through the spontaneous flocculation method, resulting in the formation of new heterogeneous LDHs-POMs catalysts Mg3Al-LnW(10) (Ln = Eu, Tb and Dy). The synthetic method can prevent Mg2+/Al3+ cations leaching out of the LDHs during intercalation and successfully control the final Mg2+/Al3+ ratio in the corresponding (MgAl)-Al-3-LnW(10). Most importantly, the as-prepared Mg3Al-LnW(10) can be obtained without the formation of the impurity phase. The heterogeneous Mg3Al-EuW10 exhibits highly efficient catalytic reactivity for cyanosilylation of various aldehydes and ketones under solvent-free conditions. The Mg3Al-EuW10 can be easily recovered and reused for at least 10 times without obvious decrease of catalytic activity and the composition and the structure of the Mg3Al-EuW10 catalyst remain stable. Moreover, the Mg3Al-EuW10-catalyzed cyanosilylation of benzaldehyde and hexanal gives the highest TON of 119,950 and 119,906, respectively. (c) 2014 Elsevier B.V. All rights reserved.
• Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls
  作者：Giacomo Strappaveccia、Daniela Lanari、Dmitri Gelman、Ferdinando Pizzo、Ornelio Rosati、Massimo Curini、Luigi Vaccaro

  DOI：10.1039/c2gc36442e

  日期：——

  and 3a–m using trimethylsilyl cyanide and triphenylphosphine supported on polystyrene as a catalyst under solvent-free conditions. It has been shown that a small amount of the catalyst allows the chemoselective 1,2-addition of trimethylsilyl cyanide to α,β-unsaturated carbonyls 1a–g (5 mol%) and to saturated carbonyls 3a–m (2 mol%). The preparation of cyanohydrin trimethylsilyl ethers 2a–g and 4a–m

  在这里，我们报告了一种可持续的协议，用于 羰基化合物 1a–g和3a–m使用三甲基甲硅烷基氰化物 和 三苯膦 支撑在聚苯乙烯上 催化剂 在下面 溶剂无条件。已经表明，少量的催化剂 允许化学选择性1,2-加成 三甲基甲硅烷基氰化物α，β-不饱和羰基1a–g（5 mol％）和饱和羰基3a–m（2 mol％）。氰醇三甲基甲硅烷基醚2a–g和4a–m的制备以良好的收率（72–99％）和非常低的E因子值（5–10）完成。最后，通过设置两种不同的流程进一步提高了效率，这使我们能够大规模进行氰醇三甲基甲硅烷基醚4a的代表性制备，E因子为0.16或0.47，减少了90％或72％与我们的批次条件相比