Tert-butyl 1,3-dihydro-2-benzofuran-5-carboxylate | 1409512-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: Tert-butyl 1,3-dihydro-2-benzofuran-5-carboxylate
• CAS: 1409512-50-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: ONCUDLZXPKKZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙炔醚 、 叔丁基丙炔酸酯 在 gold on TiO₂ 作用下， 以 正辛烷 为溶剂， 反应 18.0h， 以66%的产率得到Tert-butyl 1,3-dihydro-2-benzofuran-5-carboxylate
  参考文献：
  名称：

  Reactivity of Electron-Deficient Alkynes on Gold Nanoparticles

  摘要：

  Propiolates cyclotrimerize in the presence of catalytic amounts of gold nanoparticles to give aryl benzoates in high yields and with turnover frequencies of thousands per hour. Types of alkynes other than propiolates do not react, and, if molecular oxygen is present and dissociated by the gold nanoparticles, electron-rich arenes engage with the propiolate to form a new C-C bond. The activation of propiolates and electron-rich arenes to form C-C bonds, beyond gold-catalyzed Michael additions, constitutes a new example of how and where gold nanoparticles modify the electronic density of unsaturated C-C bonds and opens the door to future transformations.

  DOI：

  10.1021/cs400362c

文献信息

• Reactivity of Electron-Deficient Alkynes on Gold Nanoparticles
  作者：Antonio Leyva-Pérez、Judit Oliver-Meseguer、Jose R. Cabrero-Antonino、Paula Rubio-Marqués、Pedro Serna、Saud I. Al-Resayes、Avelino Corma

  DOI：10.1021/cs400362c

  日期：2013.8.2

  Propiolates cyclotrimerize in the presence of catalytic amounts of gold nanoparticles to give aryl benzoates in high yields and with turnover frequencies of thousands per hour. Types of alkynes other than propiolates do not react, and, if molecular oxygen is present and dissociated by the gold nanoparticles, electron-rich arenes engage with the propiolate to form a new C-C bond. The activation of propiolates and electron-rich arenes to form C-C bonds, beyond gold-catalyzed Michael additions, constitutes a new example of how and where gold nanoparticles modify the electronic density of unsaturated C-C bonds and opens the door to future transformations.