4-[(1H-indol-3-yl)methyl]-N,N-diethylbenzenamine | 134627-71-7

• 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: 4-[(1H-indol-3-yl)methyl]-N,N-diethylbenzenamine
• 英文别名: 3-((4-(N,N-Diethylamino)phenyl)methyl)-indole；4-((1H-indol-3-yl)methyl)-N,N-diethylaniline；N,N-diethyl-4-(1H-indol-3-ylmethyl)aniline
• CAS: 134627-71-7
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: KHJMHGYEOLDHHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 (4-Benzotriazol-1-ylmethyl-phenyl)-diethyl-amine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以95%的产率得到4-[(1H-indol-3-yl)methyl]-N,N-diethylbenzenamine
  参考文献：
  名称：

  Benzotriazole as a synthetic auxiliary: advantageous syntheses of substituted diarylmethanes and heterocyclic analogs

  摘要：

  4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation. Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dyes. Other 4-(benzotriazol-1-ylmethyl)anilines react similarly.

  DOI：

  10.1021/jo00014a014

文献信息

• ZnCl2 promoted efficient, one-pot synthesis of 3-arylmethyl and diarylmethyl indoles
  作者：Selva Ganesan Subramaniapillai、Asaithampi Ganesan

  DOI：10.1016/j.tetlet.2013.11.115

  日期：2014.1

  mediated convenient, one-pot synthesis of 3-arylmethyl and diarylmethyl indoles was accomplished in good yields. Under reaction condition, in situ formation of kinetically stable bis(indolyl)methane product was identified. Its subsequent conversion to the thermodynamically stable 3-diarylmethyl indole at elevated temperature and pressure was confirmed by carrying out pressure tube reaction with bis(indolyl)methane

  无水ZnCl 2介导的方便，一锅法合成3-芳基甲基和二芳基甲基吲哚的收率很高。在反应条件下，原位形成了动力学上稳定的双（吲哚基）甲烷产物。通过与双（吲哚基）甲烷进行压力管反应，证实了其随后在升高的温度和压力下转化为热力学稳定的3-二芳基甲基吲哚。
• Ruthenium-Catalyzed Alkylation of Indoles with Tertiary Amines by Oxidation of a sp³CH Bond and Lewis Acid Catalysis
  作者：Ming-Zhong Wang、Cong-Ying Zhou、Man-Kin Wong、Chi-Ming Che

  DOI：10.1002/chem.200902387

  日期：2010.5.17

  catalysts for direct C‐3 alkylation of indoles, giving the desired products in high yields (up to 82 % based on 60–95 % substrate conversions). These ruthenium compounds catalyze oxidative coupling reactions of a wide variety of anilines and indoles bearing electron‐withdrawing or electron‐donating substituents with high regioselectivity when using tBuOOH as an oxidant, resulting in the alkylation of N‐arylindoles

  钌卟啉（特别是[Ru（2,6-Cl 2 tpp）CO]； tpp =四苯基卟啉）和RuCl 3可以作为氧化和/或路易斯酸催化剂，用于吲哚的直接C-3烷基化，从而以高纯度得到所需的产物收率（基于60–95％的底物转化率，最高可达82％）。当使用t BuOOH作为氧化剂时，这些钌化合物催化具有高区域选择性的带有吸电子或给电子取代基的各种苯胺和吲哚的氧化偶联反应，导致N-芳基吲哚烷基化为3-[[[ N -芳基-N-烷基）氨基]甲基}吲哚（收率：最高82％，转化率：最高95％）和N的烷基化-烷基或N -H吲哚成3- [对-（二烷基氨基）苄基]吲哚（收率：最高73％，转化率：最高92％）。提议涉及两个途径的暂定反应机理：可以由SP的氧化而生成的中间亚胺离子3 Ç 由oxoruthenium物种的烷基化苯胺的H键; 然后该亚胺离子可能被N-芳基吲哚捕获（途径A）或转化为甲醛，随后在路易斯的存在下，原
• A novel multi-component reaction of indole, formaldehyde, and tertiary aromatic amines
  作者：Atul Kumar、Siddharth Sharma、Ram Awatar Maurya

  DOI：10.1016/j.tetlet.2009.08.046

  日期：2009.10

  A novel multi-component reaction of indoles, formaldehydes, and tertiary aromatic amines is described for the synthesis of dialkylaminoarylated indoles using silica-supported perchloric acid (HClO4–SiO2) as an inexpensive and highly efficient catalyst. The key features of this multi-component reactions are operational simplicity, mild reaction conditions, regioselectivity, and recycling of catalyst

  描述了一种新颖的吲哚，甲醛和芳族叔胺的多组分反应，该反应使用二氧化硅负载的高氯酸（HClO 4 -SiO 2）作为廉价且高效的催化剂来合成二烷基氨基芳基化的吲哚。这种多组分反应的关键特征是操作简便，温和的反应条件，区域选择性和催化剂的循环利用。
• KATRIZKY, ALAN R.;LAN, XIANGFU;LAM, JAMSHED N., J. ORG. CHEM., 56,(1991) N4, C. 4397-4403
  作者：KATRIZKY, ALAN R.、LAN, XIANGFU、LAM, JAMSHED N.

  DOI：——

  日期：——
• Benzotriazole as a synthetic auxiliary: advantageous syntheses of substituted diarylmethanes and heterocyclic analogs
  作者：Alan R. Katritzky、Xiangfu Lan、Jamshed N. Lam

  DOI：10.1021/jo00014a014

  日期：1991.7

  4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation. Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dyes. Other 4-(benzotriazol-1-ylmethyl)anilines react similarly.