(5-nitro-1H-indol-3-yl)-(2-nitrophenyl)methanol | 1415030-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5-nitro-1H-indol-3-yl)-(2-nitrophenyl)methanol
• CAS: 1415030-48-6
• 化学式: C₁₅H₁₁N₃O₅
• 分子量: 313.269
• InChiKey: IRPPXRFEUZDZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-nitro-1H-indol-3-yl)-(2-nitrophenyl)methanol 在 咪唑 、 C₇₂H₄₅NO₆P₂ 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 42.5h， 生成
  参考文献：
  名称：

  Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions

  摘要：

  The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.

  DOI：

  10.1021/ol403680c
• 作为产物：
  描述：

  5-硝基吲哚 、 邻硝基苯甲醛 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到(5-nitro-1H-indol-3-yl)-(2-nitrophenyl)methanol
  参考文献：
  名称：

  Cesium carbonate mediated synthesis of 3-(α-hydroxyaryl)indoles

  摘要：

  A series of 3-(alpha-hydroxyaryl)indoles have been synthesized by the reaction of aromatic aldehydes with indoles, catalyzed by cesium carbonate in DMF medium. The reactivity of the various alkali metal carbonates is discussed. The stability of 3-(alpha-hydroxyaryl)indoles is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.002

文献信息

• Cesium carbonate mediated synthesis of 3-(α-hydroxyaryl)indoles
  作者：Rasokkiyam Elayaraja、R. Joel Karunakaran

  DOI：10.1016/j.tetlet.2012.10.002

  日期：2012.12

  A series of 3-(alpha-hydroxyaryl)indoles have been synthesized by the reaction of aromatic aldehydes with indoles, catalyzed by cesium carbonate in DMF medium. The reactivity of the various alkali metal carbonates is discussed. The stability of 3-(alpha-hydroxyaryl)indoles is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions
  作者：Ming-Hua Zhuo、Yi-Jun Jiang、Yan-Sen Fan、Yang Gao、Song Liu、Suoqin Zhang

  DOI：10.1021/ol403680c

  日期：2014.2.21

  The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.