3,3′-(1-phenylethane-1,1-diyl)bis(5-nitro-1H-indole) | 1275586-52-1

• 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: 3,3′-(1-phenylethane-1,1-diyl)bis(5-nitro-1H-indole)
• 英文别名: 5-nitro-3-[1-(5-nitro-1H-indol-3-yl)-1-phenylethyl]-1H-indole
• CAS: 1275586-52-1
• 化学式: C₂₄H₁₈N₄O₄
• 分子量: 426.431
• InChiKey: WSNQAFXDCVBEGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-硝基吲哚 、 苯乙酮 在 potassium hydrogensulfate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以42%的产率得到3,3′-(1-phenylethane-1,1-diyl)bis(5-nitro-1H-indole)
  参考文献：
  名称：

  Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties

  摘要：

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.12.004

文献信息

• Decarboxylative Addition of Propiolic Acids with Indoles to Synthesize Bis(indolyl)methane Derivatives with a Pd(II)/LA Catalyst
  作者：Miao Zeng、Jing-Wen Xue、Hongwu Jiang、Kaiwen Li、Yunong Chen、Zhuqi Chen、Guochuan Yin

  DOI：10.1021/acs.joc.1c00762

  日期：2021.6.18

  introduces a Pd(II)/LA-catalyzed (LA: Lewis acid) decarboxylative addition reaction for the synthesis of bis(indolyl)methane derivatives. The presence of Lewis acid such as Sc(OTf)3 triggered Pd(II)-catalyzed decarboxylative addition of propiolic acids with indoles to offer the bis(indolyl)methane derivatives in moderate to good yields, whereas neither Pd(II) nor Lewis acid alone was active for this synthesis

  探索高效有机合成的新方案对于药物开发至关重要。本工作介绍了用于合成双（吲哚基）甲烷衍生物的 Pd（II）/LA 催化（LA：路易斯酸）脱羧加成反应。路易斯酸如 Sc(OTf) 3 的存在触发了 Pd(II) 催化的丙炔酸与吲哚的脱羧加成，以中等至良好的产率提供双（吲哚基）甲烷衍生物，而 Pd(II) 和路易斯酸都没有单独对这种合成有活性。Pd(OAc) 2的催化效率高度依赖于添加的路易斯酸的路易斯酸度，即更强的路易斯酸提供更高的双（吲哚基）甲烷衍生物产率。同时，这种 Pd(II)/LA 催化的脱羧加成反应对吲哚骨架和丙炔酸的苄基环上的多功能富电子或缺电子取代基显示出良好的耐受性。对该 Pd(II)/Sc(III) 催化的原位1 H NMR 动力学的研究揭示了由吡咯加成到炔基-Pd 生成的瞬态乙烯基-Pd(II)/Sc(III) 中间体的形成脱羧后的 (II)/Sc(III) 物种，这在之前几乎没有观察到。
• Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes
  作者：Euan B. McLean、Francesca M. Cutolo、Orla J. Cassidy、David J. Burns、Ai-Lan Lee

  DOI：10.1021/acs.orglett.0c02526

  日期：2020.9.4

  Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.
• Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties
  作者：Litao Wang、Wei Wei、Yong Guo、Jian Xu、Shijun Shao

  DOI：10.1016/j.saa.2010.12.004

  日期：2011.2

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.