4-Methyl-6-phenyl-1-propan-2-yl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2(10),3(7),5,8,12-pentaene | 1202458-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-Methyl-6-phenyl-1-propan-2-yl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2(10),3(7),5,8,12-pentaene
• CAS: 1202458-75-0
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: JDDZPNGPHWGWIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-异丙基呋喃 、 6,7-dibromo-1-methyl-3-phenyl-1H-indole 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 生成 、 4-Methyl-6-phenyl-1-propan-2-yl-14-oxa-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2(10),3(7),5,8,12-pentaene
  参考文献：
  名称：

  Experimental and Theoretical Investigations into the Unusual Regioselectivity of 4,5-, 5,6-, and 6,7-Indole Aryne Cycloadditions

  摘要：

  The 6,7-indolyne shows remarkable regioselectivity in its cycloaddition with 2-substituted furans. Electron-donating groups give predominantly the more sterically crowded product, while electron-withdrawing groups display the opposite regioselectivity, By contrast, 4,5- and 5,6-indolynes show no regioselectivity. Optimized electronic structure calculations using the M06-2X density functional and 6-311+G(2df,p) basis set revealed that the 6,7-indolynes are highly polar structures and that their cycloadditions have substantial electrophilic substitution character that leads to the observed preference for contrasteric products.

  DOI：

  10.1021/ol902415s