3-[1-(1-naphthyl)prop-2-en-1-yl]-1H-indole | 1051488-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[1-(1-naphthyl)prop-2-en-1-yl]-1H-indole
• 英文别名: 3-(1-naphthalen-1-ylprop-2-enyl)-1H-indole
• CAS: 1051488-52-8
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: RLBDNWVBIISLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-萘甲醛 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 硫酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 3-[1-(1-naphthyl)prop-2-en-1-yl]-1H-indole
  参考文献：
  名称：

  Iridium-Catalyzed C-3 Allylation of Indoles with Allylic Alcohols Promoted by a Brønsted Acid

  摘要：

  A highly regioselective method has been developed for the allylation of indoles with an iridium catalyst. This regioselective procedure uses allylic alcohols directly as allylating agents in the presence of a catalytic amount of sulfuric acid. A wide range of indoles reacted smoothly with asymmetrical allylic alcohols to give the corresponding branched products in branched-to-linear ratios of up to 99: 1 and yields as high as 92%. A series of inorganic and organic acids were tested in this approach, and it was shown that acids with pK(a) values in acetonitrile of less than 15 are required in this iridium-catalyzed system.

  DOI：

  10.1055/s-0033-1341156

文献信息

• Iridium-Catalyzed C-3 Allylation of Indoles with Allylic Alcohols Promoted by a Brønsted Acid
  作者：Chun Cai、Shu-jie Chen、Guo-ping Lu

  DOI：10.1055/s-0033-1341156

  日期：——

  A highly regioselective method has been developed for the allylation of indoles with an iridium catalyst. This regioselective procedure uses allylic alcohols directly as allylating agents in the presence of a catalytic amount of sulfuric acid. A wide range of indoles reacted smoothly with asymmetrical allylic alcohols to give the corresponding branched products in branched-to-linear ratios of up to 99: 1 and yields as high as 92%. A series of inorganic and organic acids were tested in this approach, and it was shown that acids with pK(a) values in acetonitrile of less than 15 are required in this iridium-catalyzed system.