3-(2-nitro-1-o-tolylethyl)-1H-indole | 1202694-50-5

• 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-(2-nitro-1-o-tolylethyl)-1H-indole
• 英文别名: 3-(1-(2-methylphenyl)-2-nitroethyl)-1H-indole；3-[1-(2-methylphenyl)-2-nitroethyl]-1H-indole
• CAS: 1202694-50-5
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: BCDHUHYXMMGKOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 1-甲基-2-[(E)-2-硝基乙烯基]苯 在 HY zeolite 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以89%的产率得到3-(2-nitro-1-o-tolylethyl)-1H-indole
  参考文献：
  名称：

  Michael addition of indoles to β-nitrostyrenes catalyzed by HY zeolite under solvent-free conditions

  摘要：

  Michael addition of indoles to beta-nitrostyrenes is reported using HY zeolite as catalyst under mild reaction conditions. This methodology allows the synthesis of various indole derivatives in good to high yields at 50 C under solvent-free conditions. The short reaction time and achieving high yield of the desired products are the main advantages of the present work. The catalyst can be easily recovered and reused for six successive runs without considerable changes in yields. This Michael addition catalyzed by HY zeolite is operationally simple and can be considered as a greener protocol as it avoids the use of corrosive acids and toxic reagents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.112

文献信息

• An efficient class of bis-NHC salts: applications in Pd-catalyzed reactions under mild reaction conditions
  作者：Chien-Cheng Chiu、Hui-Tzu Chiu、Dong-Sheng Lee、Ta-Jung Lu

  DOI：10.1039/c8ra04094j

  日期：——

  (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.

  这项研究描述了一类有效的双-N-杂环卡宾 (bis-NHC) 盐，可以很容易地由市售且廉价的起始材料制成。描述了这些盐在 Pd 催化反应中的应用。原位生成的钯 (Pd) 催化剂在温和的反应条件下非常有效。
• Water-soluble (salicyladimine)₂Cu complex as an efficient and renewable catalyst for Michael addition of indoles to nitroolefins in water
  作者：Haojie Jiang、Jie Zhang、Jianwei Xie、Ping Liu、Mei Xue

  DOI：10.1080/00397911.2016.1258478

  日期：2017.2.1

  ABSTRACT An efficient and environmentally friendly protocol has been demonstrated for water-soluble (salicyladimine)2Cu complex-catalyzed Michael addition of indoles to nitroolefins in water at 30 °C. A variety of substituted indoles and β-nitrostyrenes could be worked well to provide the title products in 81–97% yields. Moreover, the catalyst can be reused directly at least for four times without

  摘要 在 30 °C 下，水溶性（水杨酸二亚胺）2Cu 络合物催化吲哚与硝基烯烃迈克尔加成反应是一种高效且环保的方案。各种取代的吲哚和 β-硝基苯乙烯可以很好地工作，以 81-97% 的产率提供标题产品。此外，催化剂可以直接重复使用至少四次，而不会显着降低活性。图形概要
• Oxidative organophotoredox catalysis: a regioselective synthesis of 2-nitro substituted imidazopyridines and 3-substituted indoles, initiated by visible light
  作者：Snehlata Yadav、Madhulika Srivastava、Pratibha Rai、Bhartendu Pati Tripathi、Anu Mishra、Jaya Singh、Jagdamba Singh

  DOI：10.1039/c6nj02365g

  日期：——

  example of green chemistry, due to the fact that molecular oxygen and visible light have been utilized effectively for the transformation. The procedure involves intramolecular C–N heterocyclization, followed by aerobic oxidation and C–C bond formation at room temperature. This green protocol has also been successfully extended to the regioselective synthesis of 3-substituted indoles via indole and nitroalkene

  我们建立了一种温和，无金属，一锅，可见光催化的程序，用于在开放气氛下通过硝基烯烃和2-氨基吡啶高度区域选择性合成2-硝基-3-芳基咪唑并[1,2- a ]吡啶。一种光氧化还原催化剂曙红Y，它是一种廉价的有机染料，已在转化中用作光敏剂。由于已将分子氧和可见光有效地用于转化，因此该方案可作为绿色化学的一个实例。该过程涉及分子内C–N杂环化，然后在室温下进行好氧氧化和C–C键形成。此绿色方案也已成功扩展到3-取代吲哚的区域选择性合成通过吲哚和硝基烯烃通过自由基途径。
• 2,6-Bis(amido)benzoic Acid with Internal Hydrogen Bond as Brønsted Acid Catalyst for Friedel-Crafts Reaction of Indoles
  作者：Katsuhiko Moriyama、Toru Sugiue、Yuki Saito、Shoichi Katsuta、Hideo Togo

  DOI：10.1002/adsc.201401189

  日期：2015.6.15

  Benzoic acid catalysts bearing two amide groups that increase the Brønsted acidity of the carboxylic acid moiety by internal hydrogen‐bonding interactions were designed as a novel class of carboxylic acid catalysts for the Friedel–Crafts reaction of indoles with β‐nitrostyrenes and 3,3‐disubstituted 3H‐indoles to obtain the corresponding Friedel–Crafts adducts in high yields. The internal hydrogen‐bonding

  带有两个酰胺基团的苯甲酸催化剂通过内部氢键相互作用增加了羧酸部分的布朗斯台德酸度，被设计为一类新型的羧酸催化剂，用于吲哚与β-硝基苯乙烯和3,3-的Friedel-Crafts反应。双取代的3 H吲哚，以高收率获得相应的Friedel-Crafts加合物。与内部氢键结合的苯甲酸催化剂相比，苯胺酸具有较高的布朗斯台德酸度，后者基于DMSO中通过紫外分光光度滴定法测得的p K a得出。
• Synthesis of 2-Indolyl-1-nitroalkane Derivatives Using Nanocrystalline Titanium(IV) Oxide
  作者：M. Lakshmi Kantam、Soumi Laha、Jagjit Yadav、P. Srinivas

  DOI：10.1080/00397910902883728

  日期：2009.10.21

  The catalytic Friedel-Crafts alkylation of indoles with nitroalkenes to furnish 2-indolyl-1-nitroalkane derivatives at room temperature with moderate to excellent yields is reported using nanocrystalline titanium(IV) oxide (nano-TiO2) catalyst. In all cases, a single regioisomer was obtained. After completion of the reaction, the catalyst was recovered by centrifugation and activated under a nitrogen flow for 1h at 250 degrees C for further reuse. The nano-TiO2 can be reused for four cycles with a slight decrease of activity under the same reaction conditions.