3-(1-(naphthalen-2-yl)-2-nitroethyl)-1H-indole | 1046140-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-(naphthalen-2-yl)-2-nitroethyl)-1H-indole
• 英文别名: 3-(1-naphthalen-2-yl-2-nitroethyl)-1H-indole
• CAS: 1046140-10-6
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: FGWZEIUPVRHCBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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 、 2-(2-nitrovinyl)naphthalene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90%的产率得到3-(1-(naphthalen-2-yl)-2-nitroethyl)-1H-indole
  参考文献：
  名称：

  An Efficient Method for the N-Bromosuccinimide Catalyzed Synthesis of Indolyl-Nitroalkanes

  摘要：

  描述了一种由溴代琥珀酰亚胺催化的高效实用的吲哚基-亚硝基烷烃衍生物合成方法。通过将不同的β-硝基苯乙烯与各种取代吲哚反应，证明了该方法的普遍性，合成了一系列多样化的3-取代吲哚衍生物。这种方法的优点在于简单的反应条件和良好的吲哚基-亚硝基烷烃产率。

  DOI：

  10.3390/molecules14103952

文献信息

• Efficient synthesis of 2-indolyl-1-nitroalkanes catalyzed by tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate
  作者：Elham Safaei、Sara Sobhani、Nasrin Razavi

  DOI：10.1142/s1088424612004549

  日期：2012.2

  A new method for the synthesis of 2-indolyl-1-nitroalkanes from indoles and β-nitrostyrene via Michael addition catalyzed by [ Cu (3,4-tmtppa)] (MeSO₄)₄ as a reusable catalyst under solvent-free conditions is described. This method has been also successfully applied for Michael addition of 3-methyl-1-phenyl-5-pyrazolone with β-nitrostyrenes.

  本文介绍了一种在无溶剂条件下以[Cu (3,4-tmtppa)] (MeSO4)4为可重复使用催化剂，通过迈克尔加成法从吲哚和β-硝基苯乙烯合成 2-吲哚基-1-硝基烷烃的新方法。该方法还被成功应用于 3-甲基-1-苯基-5-吡唑酮与 β-硝基苯烯的迈克尔加成反应。
• An Efficient Method for the N-Bromosuccinimide Catalyzed Synthesis of Indolyl-Nitroalkanes
  作者：Chun-Wei Kuo、Chun-Chao Wang、Hu-Lin Fang、B. Raju、Veerababurao Kavala、Pateliya Habib、Ching-Fa Yao

  DOI：10.3390/molecules14103952

  日期：——

  An efficient and practical method for the synthesis of indolyl-nitroalkane derivatives catalyzed by N-bromosuccinimide is described. The generality of this method was demonstrated by synthesizing an array of diverse 3-substituted indole derivatives by the reaction of different β-nitrostyrenes with various substituted indoles. Simple reaction conditions accompanied by good yields of indolyl-nitroalkanes are the merits of this methodology.

  描述了一种由溴代琥珀酰亚胺催化的高效实用的吲哚基-亚硝基烷烃衍生物合成方法。通过将不同的β-硝基苯乙烯与各种取代吲哚反应，证明了该方法的普遍性，合成了一系列多样化的3-取代吲哚衍生物。这种方法的优点在于简单的反应条件和良好的吲哚基-亚硝基烷烃产率。
• Enantioselective Friedel−Crafts Alkylation of Indoles with Nitroalkenes Catalyzed by Bifunctional Tridentate Bis(oxazoline)−Zn(II) Complex
  作者：Shao-Feng Lu、Da-Ming Du、Jiaxi Xu

  DOI：10.1021/ol060586f

  日期：2006.5.1

  [reaction: see text] A more practical and efficient catalytic asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes using bifunctional tridentate bis(oxazoline)-Zn(OTf)(2) as catalyst has been developed. Various types of the nitroalkylated indoles were obtained in excellent yields (85-99%) and high enantioselectivities (up to 98% ee).

  [反应：见正文]已经开发了一种更加实用和有效的催化催化剂，它以双官能三齿双（恶唑啉）-Zn（OTf）（2）为催化剂，用硝基烯烃对吲哚进行不对称的Friedel-Crafts烷基化反应。以优异的产率（85-99％）和高对映选择性（高达98％ee）获得了各种类型的硝基烷基化的吲哚。
• Catalyst free conjugate addition of indoles and pyrroles to nitro alkenes under solvent free condition (SFC): an effective greener route to access 3-(2-nitro-1-phenylethyl)-1H-indole and 2-(2-nitro-1-phenylethyl)-1H-pyrrole derivatives
  作者：Pateliya Mujjamil Habib、Veerababurao Kavala、Chun-Wei Kuo、Mustafa J. Raihan、Ching-Fa Yao

  DOI：10.1016/j.tet.2010.05.104

  日期：2010.8

  Catalyst free conjugate addition of reactive hetero aromatics (pyrrole and indoles) to nitro alkenes under solvent free condition is described. This method provides several advantages, such as operational simplicity, solvent-free conditions and good yields of products. Also it is environmentally friendly and more cost effective alternative to existing protocols. (C) 2010 Elsevier Ltd. All rights reserved.
• Montmorillonite K10–Catalyzed Michael Addition of Indoles to Nitroolefins Under Solvent-Free Conditions
  作者：Wei-Yi Chen、Xin-Sheng Li

  DOI：10.1080/00397910802632555

  日期：2009.5.7

  Montmorillonite K10 is a very inexpensive and readily available reagent and efficiently catalyzes the Michael addition of indoles to nitroolefins under solvent-free conditions. Reasonable to excellent yields of the desired products were obtained in most cases.