2-氟乙炔基(三甲基)硅烷 | 38346-22-4

• 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
• 中文名称: 2-氟乙炔基(三甲基)硅烷
• 英文名称: fluoro(trimethylsilyl)acetylene
• 英文别名: Silane, (fluoroethynyl)trimethyl-；2-fluoroethynyl(trimethyl)silane
• CAS: 38346-22-4
• 化学式: C₅H₉FSi
• 分子量: 116.21
• InChiKey: TXLXSKCYPYZPOY-UHFFFAOYSA-N

物化性质

• 沸点：
  75.2±23.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氟乙炔基(三甲基)硅烷 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到4-氟-1H-吡唑
  参考文献：
  名称：

  N-Arylation of 4-fluoro-5-trimethylsilyl-1H-pyrazole

  摘要：

  The 1,3-dipolar cycloaddition reaction of fluoro(trimethylsilyl)acetylene prepared in situ with an excess of diazomethane smoothly proceeded to give the corresponding 4-fluoro-5-trimethylsilyl-1H-pyrazole in 84% yield. The copper iodide-catalyzed N-arylation of the fluorinated pyrazole with a variety of aryl iodides afforded N-aryl-4-fluoropyrazoles as desilylation products in good to excellent yields. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.019
• 作为产物：
  描述：

  三甲基氯硅烷 、 偏氟乙烯 在 仲丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 生成 2-氟乙炔基(三甲基)硅烷
  参考文献：
  名称：

  N-Arylation of 4-fluoro-5-trimethylsilyl-1H-pyrazole

  摘要：

  The 1,3-dipolar cycloaddition reaction of fluoro(trimethylsilyl)acetylene prepared in situ with an excess of diazomethane smoothly proceeded to give the corresponding 4-fluoro-5-trimethylsilyl-1H-pyrazole in 84% yield. The copper iodide-catalyzed N-arylation of the fluorinated pyrazole with a variety of aryl iodides afforded N-aryl-4-fluoropyrazoles as desilylation products in good to excellent yields. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.019

文献信息

• Regio- and stereoselective synthesis of tetrasubstituted (<i>E</i>)-(2-chloro-2-fluoro-1-iodovinyl)dimethylphenylsilane and its desilylative sonogashira coupling
  作者：Rin Tanaka、Keiichi Sato、Masahiro Shiosaki、Takeshi Hanamoto

  DOI：10.1039/d2ob01827f

  日期：——

  Trihalo-substituted vinylsilane was readily synthesized in 77% yield and in an excellent regio- and stereoselective manner from in situ-generated fluorosilylacetylene, followed by the addition of I2 and NCS. The silane was committed to sequential Sonogashira coupling with various terminal acetylenes under mild conditions, affording desilylated chlorofluoro-enyne adducts in moderate to good yields.

  三卤取代的乙烯基硅烷很容易以 77% 的产率合成，并以出色的区域和立体选择性方式从原位生成的氟甲硅烷基乙炔中合成，然后添加 I 2和 NCS。硅烷致力于在温和条件下与各种末端乙炔进行连续的 Sonogashira 偶联，以中等到良好的收率提供脱甲硅烷基化的氯氟-烯炔加合物。
• N-Arylation of 4-fluoro-5-trimethylsilyl-1H-pyrazole
  作者：Takeshi Hanamoto、Yuhko Iwamoto、Kenji Yamada、Ryoko Anno

  DOI：10.1016/j.jfluchem.2007.04.019

  日期：2007.10

  The 1,3-dipolar cycloaddition reaction of fluoro(trimethylsilyl)acetylene prepared in situ with an excess of diazomethane smoothly proceeded to give the corresponding 4-fluoro-5-trimethylsilyl-1H-pyrazole in 84% yield. The copper iodide-catalyzed N-arylation of the fluorinated pyrazole with a variety of aryl iodides afforded N-aryl-4-fluoropyrazoles as desilylation products in good to excellent yields. (C) 2007 Elsevier B.V. All rights reserved.