4-(3-methoxyphenyl)but-1-ynyl-trimethylsilane | 189812-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-methoxyphenyl)but-1-ynyl-trimethylsilane
• CAS: 189812-98-4
• 化学式: C₁₄H₂₀OSi
• 分子量: 232.398
• InChiKey: VRIXNPVUMJTGMV-UHFFFAOYSA-N

物化性质

• 沸点：
  290.8±23.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenyl)but-1-ynyl-trimethylsilane 在 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 {[4-(3-Methoxyphenyl)but-1-yn-1-yl]oxy}tri(propan-2-yl)silane
  参考文献：
  名称：

  Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

  摘要：

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

  DOI：

  10.1021/ja046586x
• 作为产物：
  描述：

  [3-(trimethylsilyl)prop-2-yn-1-yl]magnesium bromide 、 3-甲氧基溴苄 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-(3-methoxyphenyl)but-1-ynyl-trimethylsilane
  参考文献：
  名称：

  Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

  摘要：

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

  DOI：

  10.1021/ja046586x

文献信息

• Synthesis of Trisubstituted Indoles on the Solid Phase via Palladium-Mediated Heteroannulation of Internal Alkynes
  作者：Han-Cheng Zhang、Kimberly K. Brumfield、Bruce E. Maryanoff

  DOI：10.1016/s0040-4039(97)00417-6

  日期：1997.4

  Palladium-mediated heteroannulation of internal alkynes with resin-bound o-iodoaniline derivatives 4 or 5a provided diverse trisubstituted indoles 6 in good yields. The facile reaction of trimethylsilylalkynes afforded resin-bound precursors useful for obtaining other 2-substituted indole derivatives, such as 12. © 1997 Elsevier Science Ltd.

  钯介导的内部炔与树脂结合的邻碘苯胺衍生物4或5a的异环化反应可提供多种三取代的吲哚6，收率很高。三甲基甲硅烷基炔烃的简便反应提供了可用于获得其他2取代的吲哚衍生物，如12的树脂结合的前体。©1997爱思唯尔科学有限公司。
• The utility of the coupling reaction between propargyl grignard reagent and allylic halides for the synthesis of acetylenes
  作者：Robert E. Ireland、Marcia I. Dawson、Christopher A. Lipinski

  DOI：10.1016/s0040-4039(01)98200-0

  日期：1970.1