triethyl(naphthalen-1-ylethynyl)silane | 1446713-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: triethyl(naphthalen-1-ylethynyl)silane
• 英文别名: Triethyl(2-naphthalen-1-ylethynyl)silane；triethyl(2-naphthalen-1-ylethynyl)silane
• CAS: 1446713-42-3
• 化学式: C₁₈H₂₂Si
• 分子量: 266.458
• InChiKey: CDQUGYBRXJMVRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  三乙基(碘)硅烷 、 1-乙炔基萘 在 [{Ir(μ-Cl)(CO)2}2] 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以73%的产率得到triethyl(naphthalen-1-ylethynyl)silane
  参考文献：
  名称：

  A new and efficient route for the synthesis of alkynyl functionalized silicon derivatives

  摘要：

  The iridium-based catalytic system, [{Ir(mu-Cl)(CO)(2)}(2)]/NEt(i-Pr)(2), was examined in the coupling reaction of iodotrisubstituted silanes (R3SiI) with various terminal arylalkynes ((RC)-C-1 CH). Under optimum conditions, the process occurs very efficiently (in particular for Me3SiI and Me2PhSiI), giving exclusively the respective C-sp-silyl functionalized alkynes ((RC)-C-1 CSiR3). Additionally, this iridium-based catalytic system was successfully used for the preparation of selected bis(phenylethynyl) disubstituted silanes [(R2Si)-Si-2(C CPh)(2)] via coupling of phenylacetylene with appropriate diiodo-disubstituted silanes ((R2SiI2)-Si-2). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.103

文献信息

• Heterogeneously Catalyzed Aerobic Cross-Dehydrogenative Coupling of Terminal Alkynes and Monohydrosilanes by Gold Supported on OMS-2
  作者：Kazuya Yamaguchi、Ye Wang、Takamichi Oishi、Yoshiyuki Kuroda、Noritaka Mizuno

  DOI：10.1002/anie.201300988

  日期：2013.5.17

  Cross‐dehydrogenative coupling of various terminal alkynes and monohydrosilanes efficiently proceeded in the presence of gold supported on OMS‐2 (Au/OMS‐2) using O2 as a terminal oxidant, affording the corresponding alkynylsilanes in moderate to high yields (see picture). The observed catalysis was truly heterogeneous, and the catalyst could be reused at least ten times without a significant loss of

  在OMS-2（Au / OMS-2）上负载金的情况下，使用O 2作为末端氧化剂，可以有效地进行各种末端炔烃和一氢硅烷的交叉脱氢偶联反应，从而以中等至高收率提供相应的炔基硅烷（参见图片） 。观察到的催化确实是非均相的，并且该催化剂可以重复使用至少十次，而不会显着降低其高催化性能。
• A new and efficient route for the synthesis of alkynyl functionalized silicon derivatives
  作者：Ireneusz Kownacki、Bartosz Orwat、Bogdan Marciniec、Agnieszka Kownacka

  DOI：10.1016/j.tetlet.2013.11.103

  日期：2014.1

  The iridium-based catalytic system, [Ir(mu-Cl)(CO)(2)}(2)]/NEt(i-Pr)(2), was examined in the coupling reaction of iodotrisubstituted silanes (R3SiI) with various terminal arylalkynes ((RC)-C-1 CH). Under optimum conditions, the process occurs very efficiently (in particular for Me3SiI and Me2PhSiI), giving exclusively the respective C-sp-silyl functionalized alkynes ((RC)-C-1 CSiR3). Additionally, this iridium-based catalytic system was successfully used for the preparation of selected bis(phenylethynyl) disubstituted silanes [(R2Si)-Si-2(C CPh)(2)] via coupling of phenylacetylene with appropriate diiodo-disubstituted silanes ((R2SiI2)-Si-2). (C) 2013 Elsevier Ltd. All rights reserved.