triethyl(4-aminophenylethynyl)silane | 1421764-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triethyl(4-aminophenylethynyl)silane
• 英文别名: 4-(2-Triethylsilylethynyl)aniline；4-(2-triethylsilylethynyl)aniline
• CAS: 1421764-15-9
• 化学式: C₁₄H₂₁NSi
• 分子量: 231.413
• InChiKey: XMOFOIWOWHLJDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triethyl(4-aminophenylethynyl)silane 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 生成
  参考文献：
  名称：

  Nanostructured Monolayers on Carbon Substrates Prepared by Electrografting of Protected Aryldiazonium Salts

  摘要：

  The electrogeneration of aryl radicals from protected diazonium salts combined with protection-deprotection steps was evaluated to design functional monolayers on carbon substrates with a well-controlled organization at the nanometric scale. The structure of the obtained monolayer is adjusted by varying the size of the protecting group that is introduced on the precursors (trimethylsilyl, triethylsilyl, and tri(isopropyl)silyl were tested in the present study). After deprotection, a robust ethynylaryl monolayer is obtained whatever the substituent that serves as a platform to attach other functional groups by a specific "click chemistry" coupling step. Electrochemical and structural analyses show that the organization of the attached monolayer is totally governed by the size of the protecting group that leaves a footprint after removal but maintains a total availability of the immobilized functional groups. Properties of the monolayer (charge transfer, permeation of molecules through the layer, density of functional groups) were examined in combination with the performances for postfunctionalization taken with an alkyl-ferrocene derivative as an example of the immobilized species.

  DOI：

  10.1021/cm303844v
• 作为产物：
  描述：

  三乙基矽乙炔 、 对碘苯胺 在 四(三苯基膦)钯 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以79%的产率得到triethyl(4-aminophenylethynyl)silane
  参考文献：
  名称：

  Nanostructured Monolayers on Carbon Substrates Prepared by Electrografting of Protected Aryldiazonium Salts

  摘要：

  The electrogeneration of aryl radicals from protected diazonium salts combined with protection-deprotection steps was evaluated to design functional monolayers on carbon substrates with a well-controlled organization at the nanometric scale. The structure of the obtained monolayer is adjusted by varying the size of the protecting group that is introduced on the precursors (trimethylsilyl, triethylsilyl, and tri(isopropyl)silyl were tested in the present study). After deprotection, a robust ethynylaryl monolayer is obtained whatever the substituent that serves as a platform to attach other functional groups by a specific "click chemistry" coupling step. Electrochemical and structural analyses show that the organization of the attached monolayer is totally governed by the size of the protecting group that leaves a footprint after removal but maintains a total availability of the immobilized functional groups. Properties of the monolayer (charge transfer, permeation of molecules through the layer, density of functional groups) were examined in combination with the performances for postfunctionalization taken with an alkyl-ferrocene derivative as an example of the immobilized species.

  DOI：

  10.1021/cm303844v

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。
• Nanostructured Monolayers on Carbon Substrates Prepared by Electrografting of Protected Aryldiazonium Salts
  作者：Yann R. Leroux、Philippe Hapiot

  DOI：10.1021/cm303844v

  日期：2013.2.12

  The electrogeneration of aryl radicals from protected diazonium salts combined with protection-deprotection steps was evaluated to design functional monolayers on carbon substrates with a well-controlled organization at the nanometric scale. The structure of the obtained monolayer is adjusted by varying the size of the protecting group that is introduced on the precursors (trimethylsilyl, triethylsilyl, and tri(isopropyl)silyl were tested in the present study). After deprotection, a robust ethynylaryl monolayer is obtained whatever the substituent that serves as a platform to attach other functional groups by a specific "click chemistry" coupling step. Electrochemical and structural analyses show that the organization of the attached monolayer is totally governed by the size of the protecting group that leaves a footprint after removal but maintains a total availability of the immobilized functional groups. Properties of the monolayer (charge transfer, permeation of molecules through the layer, density of functional groups) were examined in combination with the performances for postfunctionalization taken with an alkyl-ferrocene derivative as an example of the immobilized species.