4-chloro-2-(triethylsilylethynyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-2-(triethylsilylethynyl)phenol
• 英文别名: 4-Chloro-2-(2-triethylsilylethynyl)phenol
• 化学式: C₁₄H₁₉ClOSi
• 分子量: 266.843
• InChiKey: NIGYRAACECZEKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  17
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对氯苯酚 在 gallium(III) trichloride 、 正丁基锂 作用下， 以 正己烷 、 邻二氯苯 为溶剂， 反应 0.17h， 以87%的产率得到4-chloro-2-(triethylsilylethynyl)phenol
  参考文献：
  名称：

  GaCl₃-Catalyzed Ortho-Ethynylation of Phenols

  摘要：

  Phenols are ethynylated at the ortho position with silylated chloroethyne in the presence of a catalytic amount of GaCl3 and lithium phenoxide. The lithium salt is essential for the catalysis, and addition of 2,6-di(tert-butyl)-4-methylpyridine inhibits desilylation and hydration of the products. The reaction can be applied to various substituted phenols giving the ortho-ethynylated products in high yields, and the turnover numbers based on GaCl3 are between 8 and 10. The reaction mechanism involves addition of in situ formed phenoxygallium to the haloethyne followed by the elimination of GaCl3.

  DOI：

  10.1021/ja026108r

文献信息

• GaCl₃-Catalyzed Ortho-Ethynylation of Phenols
  作者：Katsumi Kobayashi、Mieko Arisawa、Masahiko Yamaguchi

  DOI：10.1021/ja026108r

  日期：2002.7.1

  Phenols are ethynylated at the ortho position with silylated chloroethyne in the presence of a catalytic amount of GaCl3 and lithium phenoxide. The lithium salt is essential for the catalysis, and addition of 2,6-di(tert-butyl)-4-methylpyridine inhibits desilylation and hydration of the products. The reaction can be applied to various substituted phenols giving the ortho-ethynylated products in high yields, and the turnover numbers based on GaCl3 are between 8 and 10. The reaction mechanism involves addition of in situ formed phenoxygallium to the haloethyne followed by the elimination of GaCl3.