5-nitro-3-[(5-nitro-1H-indol-3-yl)-(4-nitrophenyl)methyl]-1H-indole | 891828-48-1

• 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: 5-nitro-3-[(5-nitro-1H-indol-3-yl)-(4-nitrophenyl)methyl]-1H-indole
• CAS: 891828-48-1
• 化学式: C₂₃H₁₅N₅O₆
• 分子量: 457.402
• InChiKey: YJHYFPFCEXOBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基吲哚 、 对硝基苯甲醛 在 sulfonated rice husk ash 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以94%的产率得到5-nitro-3-[(5-nitro-1H-indol-3-yl)-(4-nitrophenyl)methyl]-1H-indole
  参考文献：
  名称：

  Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds

  摘要：

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。

  DOI：

  10.1039/c3ra44053b

文献信息

• Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds
  作者：Mohadeseh Seddighi、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1039/c3ra44053b

  日期：——

  Sulfonated rice husk ash (RHA-SO3H), a newly reported solid acid catalyst, was efficiently used for the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols), 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins) and bis(indolyl)methanes. The procedure gave the products in excellent yields within very short reaction times under mild and green conditions. Also this catalyst can be reused several times without appreciable loss of its catalytic activity.

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。
• Oxalate capped iron nanomaterial: from methylene blue degradation to bis(indolyl)methane synthesis
  作者：Rupa Pegu、Krishna Joyti Majumdar、Dhruba Joyti Talukdar、Sanjay Pratihar

  DOI：10.1039/c4ra04214j

  日期：——

  high-temperature calcination. The oxidation of Fe(0) to Fe3O4 at room temperature in open air leads to Fe-oxalate capped Fe3O4 [Fe(ox)–Fe3O4] nanomaterial on the gram scale. The Fe(ox)–Fe3O4 nanomaterial is found to be useful as a magnetically recoverable catalyst for the selective synthesis of bis(indolyl)methanes from the condensation between aldehydes and indoles in water. The as-prepared Fe(ox)–Fe3O4

  利用硼氢化钠（NaBH 4）还原铁（II）盐开发了一种高效，可持续和绿色的方法，用于合成选择性斜方铁（草酸盐）封端的Fe（0）[Fe（ox）–Fe（0）]纳米材料。在草酸存在下于室温下在水中。报告的方法是一种在不进行高温煅烧的情况下以克级生产Fe（ox）–Fe（0）纳米材料的经济有效的化学途径。在室温下，露天将Fe（0）氧化为Fe 3 O 4会导致克重草酸盐封端的Fe 3 O 4 [Fe（ox）–Fe 3 O 4 ]纳米材料。Fe（ox）–Fe 3 O 4发现纳米材料可用作磁性回收的催化剂，用于从水中醛和吲哚之间的缩合选择性合成双（吲哚基）甲烷。所制备的Fe（ox）–Fe 3 O 4纳米材料还具有出色的作为可重复使用的催化剂在紫外线辐射下降解亚甲基蓝（MB）的能力，并有望在许多其他应用中使用。水性反应介质，易于合成，使用外部磁体轻松分离催化剂以及催化剂的高效回收利用使该方案经济且可持续。
• Facile Synthesis of Bis(indolyl)methanes catalyzed by Ferric Dodecyl Sulfonate [Fe(DS)₃] in Water at Room Temperature
  作者：Shun‐Yi Wang、Shun‐Jun Ji

  DOI：10.1080/00397910701873318

  日期：2008.3.28

  Abstract Ferric dodecyl sulfonate [Fe(DS)3] is easily prepared and can be used as a Lewis acid surfactant catalyst in water to conduct the highly efficient electrophilic substitution reaction of indoles with aliphatic or aromatic aldehydes at room temperature.

  摘要 十二烷基磺酸铁[Fe(DS)3]制备简单，可在水中作为路易斯酸表面活性剂催化剂，在室温下进行吲哚与脂肪族或芳香族醛的高效亲电取代反应。
• 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.
• A clean synthesis of bis(indolyl)methane and biscoumarin derivatives using P₄VPy–CuO nanoparticles as a new, efficient and heterogeneous polymeric catalyst
  作者：Farhad Shirini、Abdollah Fallah-Shojaei、Laleh Samavi、Masoumeh Abedini

  DOI：10.1039/c6ra04893e

  日期：——

  the green, simple and highly efficient synthesis of bis(indolyl)methanes and 3,3′-(arylmethylene)bis(4-hydroxycoumarins). This methodology has some advantages such as short reaction times, environmentally friendly conditions, easy work-up, and excellent yields. This catalyst can be easily separated and re-used without any appreciable loss in its activity.

  P 4 VPy-CuO纳米颗粒作为新型固体催化剂，采用超声辐照法合成，并通过X射线衍射（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM）和傅立叶变换红外光谱（FT-IR）表征）光谱学。制备的催化剂用于绿色，简单，高效的双（吲哚基）甲烷和3,3'-（芳基亚甲基）双（4-羟基香豆素）的合成。该方法具有一些优点，例如反应时间短，环境友好的条件，易于后处理和优异的收率。该催化剂可以容易地分离和重复使用，而其活性没有任何明显的损失。