1-methyl-2-nitroindole

• 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: 1-methyl-2-nitroindole
• 英文别名: 1-Methyl-2-nitro-1H-indole
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: QDNLHHNZQKBDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  间氯溴苯 、 1-methyl-2-nitroindole 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以55%的产率得到3-(m-chlorophenyl)-1-methyl-2-nitroindole
  参考文献：
  名称：

  Synthesis of 3-Aryl-2-nitroindoles by Palladium-Catalyzed CH-Activation Reactions

  摘要：

  3-Aryl-2-nitroindoles were prepared via CH-activation reactions of N-methyl-2-nitroindole.

  DOI：

  10.1055/s-0035-1560053
• 作为产物：
  描述：

  2-碘-1H-吲哚 在 氢氧化钾 、 silver(I) nitrite 、 (n-Bu)4HSO₄ 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 62.0h， 生成 1-methyl-2-nitroindole
  参考文献：
  名称：

  A convenient synthesis of 2-nitroindoles

  摘要：

  The reaction of 2-iodo- and 2-bromoindoles with silver nitrite in aqueous acetone affords the corresponding 2-nitroindoles in modest to good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.112

文献信息

• Nitration of Heteroaryltrimethyltins by Tetranitromethane and Dinitrogen Tetroxide: Mechanistic Aspects, Scope and Limitations
  作者：Valérie Fargeas、Fabien Favresse、Didier Mathieu、Isabelle Beaudet、Pierre Charrue、Bruno Lebret、Marc Piteau、Jean-Paul Quintard

  DOI：10.1002/ejoc.200210611

  日期：2003.5

  The nitration of 2-(trimethylstannyl)heteroarenes by tetranitromethane (TNM) or dinitrogen tetroxide has been shown to be possible when the HOMO energy of the heteroaryltin is high enough to allow the formation of the corresponding radical cation. The reaction proceeds through a charge-transfer complex between heteroaryltin and TNM, followed by a single-electron transfer, which is enhanced under sunlamp

  当杂芳基锡的 HOMO 能量足够高以允许形成相应的自由基阳离子时，四硝基甲烷 (TNM) 或四氧化二氮对 2-(三甲基甲锡烷基) 杂芳烃的硝化已被证明是可能的。该反应通过杂芳基锡和 TNM 之间的电荷转移复合物进行，然后是单电子转移，在太阳灯照射下增强。因此，通过该方法获得了2-硝基苯并[b]呋喃、2-硝基苯并[b]噻吩、2-硝基吡啶和2-硝基吲哚。然而，由于 HOMO 轨道的低能量，2-甲锡烷基化嘧啶或甲锡烷基化 1,3,5-三嗪的硝化已被证明是不可能的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Electrooptic chromophores with large optical birefringence for applications at high speed and short wavelengths
  申请人：McGinniss D. Vincent

  公开号：US20060106262A1

  公开（公告）日：2006-05-18

  Disclosed is a series of materials, which exhibit large birefringence under the influence of an applied electric field. These materials are capable of switching this large birefringence with a characteristic time on the order of 1 microsecond or less. In addition, these materials have good optical loss at this wavelength, and are stable under irradiation. These materials are suitable for fabrication of optical devices such a variable optical attenuators, switches, and modulators that respond in these time frames or slower. These materials are also suitable for use across a wide range of wavelengths. As a second component of this invention, some of these novel materials exhibit these desired optical properties (large birefringence, low loss, stability under illumination) at wavelengths as short as about 400 nm. These materials are suitable for fabrication of optical devices operating at or about 405 nm, where conventional EO materials strongly absorb and/or quickly degrade.

  披露了一系列材料，这些材料在受到外加电场影响下表现出较大的双折射。这些材料能够在大约1微秒或更短的时间内切换这种较大的双折射。此外，这些材料在这个波长下具有良好的光学损耗，并且在辐照下稳定。这些材料适用于制造像可变光学衰减器、开关和调制器等在这些时间范围或更慢响应的光学器件。这些材料也适用于在广泛波长范围内使用。作为本发明的第二个组成部分，一些新型材料在约400纳米的波长下展现出这些理想的光学特性（较大的双折射、低损耗、辐照下的稳定性）。这些材料适用于制造在或约405纳米波长下运行的光学器件，传统的电光材料在这个波长下会强烈吸收和/或迅速降解。
• Organotin mediated nitration in heteroaromatic series using tetranitromethane or dinitrogen tetroxide
  作者：Fabien Favresse、Valérie Fargeas、Pierre Charrue、Bruno Lebret、Marc Piteau、Jean-Paul Quintard

  DOI：10.1016/s0022-328x(99)00699-3

  日期：2000.3

  2-Trimethylstannylated benzo[b]furan, benzo[b]thiophene, N-substituted indoles and pyridine afford the corresponding nitro derivatives in regioselective fashion upon treatment with tetranitromethane (using sun-lamp irradiation in the case of N-containing heterocycles) or with dinitrogen tetroxide. (C) 2000 Elsevier Science S.A. All rights reserved.
• A convenient synthesis of 2-nitroindoles
  作者：Sujata Roy、Gordon W. Gribble

  DOI：10.1016/j.tetlet.2004.12.112

  日期：2005.2

  The reaction of 2-iodo- and 2-bromoindoles with silver nitrite in aqueous acetone affords the corresponding 2-nitroindoles in modest to good yields. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 3-Aryl-2-nitroindoles by Palladium-Catalyzed CH-Activation Reactions
  作者：Viktor Iaroshenko、Peter Langer、Anton Ivanov、Alexander Villinger

  DOI：10.1055/s-0035-1560053

  日期：——

  3-Aryl-2-nitroindoles were prepared via CH-activation reactions of N-methyl-2-nitroindole.