1-methyl-3-(4-nitrophenyl)-1H-indole | 51206-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methyl-3-(4-nitrophenyl)-1H-indole
• 英文别名: 1-Methyl-3-(4-nitrophenyl)indole
• CAS: 51206-87-2
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: HVHUWNOKRBPNNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 亚硝酸特丁酯 、 lithium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 22.33h， 生成 1-methyl-3-(4-nitrophenyl)-1H-indole
  参考文献：
  名称：

  抗坏血酸作为金自由基介导的吲哚与氯化芳重氮的芳基化反应中的芳基自由基诱导剂。

  摘要：

  近年来，对促进金的氧化添加以进入由该金属介导的温和的交叉偶联过程的方案的兴趣增加了。在此背景下，我们在本文中报道抗坏血酸是一种天然且易于获得的抗氧化剂，可用于加速芳基重氮氯化物到AuI上的氧化加成。以这种方式产生的芳基-AuIII物种已被用于以一锅法从苯胺和对位，间位和邻位取代的芳基重氮鎓氯化物制备3-芳基吲哚。基于EPR分析，循环伏安法和DFT计算，详细研究了氧化加成的潜在机理。有趣的是，我们发现在该方案中，氯化物原子诱导了AuII / AuIII氧化步骤。

  DOI：

  10.1002/chem.201904413

文献信息

• Catalytic Au(<scp>i</scp>)/Au(<scp>iii</scp>) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles
  作者：Jessica Rodriguez、Abdallah Zeineddine、E. Daiann Sosa Carrizo、Karinne Miqueu、Nathalie Saffon-Merceron、Abderrahmane Amgoune、Didier Bourissou

  DOI：10.1039/c9sc01954e

  日期：——

  electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate

  已充分研究了半不稳定（P，N）MeDalphos配体引发碘代芳烃向金的氧化加成的能力。竞争实验和Hammett相关性在化学计量氧化加成反应和与1,3,5-三甲氧基苯的催化C–C交叉偶联中都证明了金对于富电子底物的明显偏好。此特征与钯通常遇到的电子剥夺性底物的更高反应性形成鲜明对比。基于DFT计算和关键过渡状态的详细分析（特别是使用NBO，CDA和ETS-NOCV方法），提出了两种金属的不同行为，这是由于基底和金属之间的逆电子流导致的。的确，碘苯的氧化加成与金在过渡态时从基底到金属的电荷转移有关，而钯则相反。金中心的较高亲电性有利于富电子的基质，而钯的重要背向供稿则有利于电子贫乏的基质。碘代芳烃的简便氧化加成结合金的倾向（III）络合物易于与富电子（杂）芳烃反应，促使我们将（MeDalphos）AuCl络合物应用于吲哚的催化芳基化反应，这是一项具有挑战性但非常重要的转化。金络合物被证明是非常
• HFIP-Promoted Bischler Indole Synthesis under Microwave Irradiation
  作者：Guangkai Yao、Zhi-Xiang Zhang、Cheng-Bei Zhang、Han-Hong Xu、Ri-Yuan Tang

  DOI：10.3390/molecules23123317

  日期：——

  1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was found to be effective for the Bischler indole synthesis under microwave irradiation in the absence of a metal catalyst. Under the catalysis of HFIP, a wide range of α-amino arylacetones were successfully transformed into indole derivatives with moderate to good yields.

  发现 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) 在没有金属催化剂的情况下在微波辐射下对 Bischler 吲哚合成有效。在HFIP的催化下，广泛的α-氨基芳基丙酮成功地转化为吲哚衍生物，产率中等至良好。
• AgONO-Assisted Direct CH Arylation of Heteroarenes with Anilines
  作者：Saravanan Gowrisankar、Jayasree Seayad

  DOI：10.1002/chem.201403640

  日期：2014.9.26

  A novel copper‐catalyzed CH arylation of heteroarenes with anilines by an in situ diazonium reaction is established by using silver nitrite (AgONO) as an unconventional nitrosating reagent under acid‐free conditions. It provides a complementary approach for the CH arylation of electron‐rich heteroarenes with aromatic amines affording a variety of heterobiaryls in moderate to good yields.

  一种新颖的铜催化Ç 芳基化与苯胺通过原位重氮反应通过使用亚硝酸银（AgONO）作为无酸的条件下一个非常规的亚硝基化试剂建立杂芳烃小时。它为富电子杂芳基与芳族胺的C芳基化提供了一种补充方法，该芳族胺以中等至良好的收率提供了各种杂二芳基。
• Abnormal NHC supported palladacycles: Regioselective arylation of heteroarenes via decarboxylation
  作者：Anex Jose、Gonela Vijaykumar、Pavan K. Vardhanapu、Swadhin K. Mandal

  DOI：10.1016/j.jorganchem.2018.01.046

  日期：2018.6

  We report synthesis of two new palladium(II) complexes of abnormal N-heterocyclic carbene ligands. The catalytic activity of these palladium(II) complexes was examined for the decarboxylative arylation of N-methylindole-carboxylic acids. An exclusive regioselectivity and very good yields were obtained with a variety of aryl halide partners. (C) 2018 Elsevier B.V. All rights reserved.
• Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions
  作者：Robert J. Phipps、Neil P. Grimster、Matthew J. Gaunt

  DOI：10.1021/ja801767s

  日期：2008.7.1

  We have developed a new site-selective Cu(II)-catalyzed C-H bond funtionalization process that can selectively arlate indoles at either the C3 or C2 position under miled conditions. The scope of arylation process is broad and tolerates broad functionality on both indole and aryl unit, which makes it amenable to further elaboartion. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl that undergoes intial addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group of C3 to C2, and this can be controlled by the nature of the group on the nitrogen atm; free (NH)-and N-alkylindoles deliver the C3-arylated product, whereas N-acytylindoles affored the C2 isomer, both with excellent yield and selectivity.