2-hydroxy-3-(1H-indol-3-yl)naphthalene-1,4-dione | 1240385-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-(1H-indol-3-yl)naphthalene-1,4-dione
• CAS: 1240385-31-2
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: XVKFZWXTLYMASM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.16
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以5%的产率得到2-hydroxy-3-(1H-indol-3-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes

  摘要：

  Phenyliodonium ylide of lawsone, activated by BF3 center dot Et2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3 center dot Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.120

文献信息

• Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes
  作者：Elias Glinis、Elizabeth Malamidou-Xenikaki、Haris Skouros、Spyros Spyroudis、Maria Tsanakopoulou

  DOI：10.1016/j.tet.2010.04.120

  日期：2010.7

  Phenyliodonium ylide of lawsone, activated by BF3 center dot Et2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3 center dot Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction. (C) 2010 Elsevier Ltd. All rights reserved.