hex-1-ynyl-diphenylsilane | 153327-97-0

• 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: hex-1-ynyl-diphenylsilane
• 英文别名: Hex-1-ynyl(diphenyl)silane
• CAS: 153327-97-0
• 化学式: C₁₈H₂₀Si
• 分子量: 264.442
• InChiKey: WIKMVLFZDAITHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  hex-1-ynyl-diphenylsilane 在 四(三苯基膦)钯 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 二(三叔丁基膦)钯 、 potassium tert-butylate 、 溴 、 sodium carbonate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 105.5h， 生成
  参考文献：
  名称：

  Silicon-Tethered Strategy for Copper(I)-Catalyzed Stereo- and Regioselective Alkylboration of Alkynes

  摘要：

  Stereoselective silicon-tethered alkylboration of alkynes in the presence of a copper(I) catalyst and a diboron reagent provided the corresponding cyclic alkenylboronates in high yields (up to 99% yield) with excellent regio- and syn-selectivities (E/Z = <1:99). The products, which can be considered as the formal alkyne intermolecular alkylboration products, undergo subsequent selective derivatization, including ring opening, to give functionalized trans-stilbene derivatives.

  DOI：

  10.1021/ol503620n
• 作为产物：
  描述：

  氯化二苯基硅烷 、 叔丁基二甲基(2-丙炔氧基)硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以54%的产率得到hex-1-ynyl-diphenylsilane
  参考文献：
  名称：

  Silicon-Tethered Strategy for Copper(I)-Catalyzed Stereo- and Regioselective Alkylboration of Alkynes

  摘要：

  Stereoselective silicon-tethered alkylboration of alkynes in the presence of a copper(I) catalyst and a diboron reagent provided the corresponding cyclic alkenylboronates in high yields (up to 99% yield) with excellent regio- and syn-selectivities (E/Z = <1:99). The products, which can be considered as the formal alkyne intermolecular alkylboration products, undergo subsequent selective derivatization, including ring opening, to give functionalized trans-stilbene derivatives.

  DOI：

  10.1021/ol503620n

文献信息

• Synthesis of lanthanide(II)–imine complexes and their use in carbon–carbon and carbon–nitrogen unsaturated bond transformation
  作者：Ken Takaki、Kimihiro Komeyama、Katsuomi Takehira

  DOI：10.1016/j.tet.2003.06.003

  日期：2003.12

  1 quantitatively, the structure of which was characterized by X-ray analysis. The imine complexes 1 catalyzed dehydrogenative silylation of terminal alkynes, hydrosilylation of imines and alkenes, and intermolecular hydrophosphination of alkynes. Moreover, dehydrogenative double silylation of conjugated dienes was achieved with 1.

  和sa金属将芳香族酮亚胺还原，直接定量得到二价氮杂蒽环丙烷丙烷配合物1，其结构通过X射线分析表征。亚胺络合物1催化末端炔烃的脱氢甲硅烷基化，亚胺和烯烃的氢化硅烷化以及炔烃的分子间加氢磷酸化。此外，共轭二烯的脱氢双甲硅烷基化是用1实现的。
• Ruthenium-Catalyzed Silyl Ether Formation and Enyne Metathesis Sequence:  Synthesis of Siloxacycles from Terminal Alkenyl Alcohols and Alkynylsilanes
  作者：Reagan L. Miller、Sarah V. Maifeld、Daesung Lee

  DOI：10.1021/ol049019n

  日期：2004.8.1

  Two consecutive ruthenium-catalyzed reactions have been achieved for the synthesis of siloxacycles from terminal alkenyl carbenols and alkynylsilanes. The metal-catalyzed dehydrogenative condensation between alcohols and silanes, generating molecular hydrogen as the only byproduct, allows for the subsequent enyne metathesis without isolating the intermediate silyl ethers. This system provides a streamlined

  从末端烯基甲醇和炔基硅烷合成硅氧烷环已实现了两个连续的钌催化反应。醇和硅烷之间的金属催化的脱氢缩合反应，产生分子氢作为唯一的副产物，可进行随后的烯炔复分解，而无需分离中间体甲硅烷基醚。该系统提供了对合成有用的构建基块的简化合成。[反应：看文字]
• Calcium-catalyzed C(sp)-H silylation of terminal alkynes with hydrosilanes
  作者：Xizhou Zheng、Shengjie Jiang、Chuan Dong、Qingyun Yao、Yingming Yao、Xin Xu

  DOI：10.1016/j.poly.2022.115771

  日期：2022.5

  This work reports a C(sp)-H silylation of terminal alkynes with hydrosilanes by using a molecular calcium hydride [(DIPPnacnac)CaH(thf)}2] (DIPPnacnac = CH(CMe)(2,6-iPr2-C6H3N)}2) as a catalyst. The reaction selectively afforded monoalkynylsilanes in high isolated yields with a broad substrate scope and high atom economy. A control experiment and kinetic studies were conducted to provide some insights

  这项工作报告了通过使用分子氢化钙 [( DIPP nacnac)CaH(thf)} 2 ] ( DIPP nacnac = CH(CMe)(2,6- i Pr 2 -C 6 H 3 N)} 2 ) 作为催化剂。该反应选择性地以高分离产率提供单炔基硅烷，具有广泛的底物范围和高原子经济性。进行了对照实验和动力学研究，以提供对催化反应的一些见解。此外，所得炔基硅烷容易衍生形成其他产物。
• Dehydrogenative Silylation of Terminal Alkynes Catalyzed by Ytterbium−Imine Complexes
  作者：Ken Takaki、Masanobu Kurioka、Tohru Kamata、Katsuomi Takehira、Yoshikazu Makioka、Yuzo Fujiwara

  DOI：10.1021/jo981008i

  日期：1998.12.1

  Catalytic dehydrogenative silylation of terminal alkynes with hydrosilanes has been achieved by using divalent Yb-imine complexes; The reaction with mono-, di-, and trihydrosilanes gave the corresponding alkynylsilanes in good yields. alpha,omega-Diynes were similarly silylated at both termini. Thus, oligomers were obtained from the diynes and dihydrosilanes. In addition, it has been found that the imine complexes exhibit catalytic activity for redistribution of the silyl groups of the alkynylsilanes and for Si-Si bond fission of disilanes.