6-chloro-3-(1-(2-methylphenyl)-2-nitroethyl)-1H-indole | 1586812-89-6

• 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: 6-chloro-3-(1-(2-methylphenyl)-2-nitroethyl)-1H-indole
• 英文别名: 6-chloro-3-[1-(2-methylphenyl)-2-nitroethyl]-1H-indole
• CAS: 1586812-89-6
• 化学式: C₁₇H₁₅ClN₂O₂
• 分子量: 314.771
• InChiKey: GHLKDAKTJYSTDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 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：

  6-氯吲哚 、 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87%的产率得到6-chloro-3-(1-(2-methylphenyl)-2-nitroethyl)-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

• 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。