3-(pyrrolidin-1-yl(3,4,5-trimethoxyphenyl)methyl)-1H-indole | 1609026-95-0

• 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-(pyrrolidin-1-yl(3,4,5-trimethoxyphenyl)methyl)-1H-indole
• 英文别名: 3-[pyrrolidin-1-yl-(3,4,5-trimethoxyphenyl)methyl]-1H-indole
• CAS: 1609026-95-0
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: VXBSNFWEAGEIRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄醇 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-四甲基哌啶氧化物 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 生成 3-(pyrrolidin-1-yl(3,4,5-trimethoxyphenyl)methyl)-1H-indole
  参考文献：
  名称：

  Iron mediated one pot three component synthesis of 3-substituted indoles via aerobic iminium ion formation

  摘要：

  An efficient and economical method was developed for the synthesis of 3 substituted indoles by a highly efficient one-pot three component coupling reaction of substituted or unsubstituted benzyl alcohol, N-methyl aniline or pyrrolidine, and indoles or substituted indoles. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.12.047

文献信息

• Natural Products for Drug Discovery: Discovery of Gramines as Novel Agents against a Plant Virus
  作者：Aidang Lu、Tienan Wang、Hao Hui、Xiaoye Wei、Weihao Cui、Chunlv Zhou、Hongyan Li、Ziwen Wang、Jincheng Guo、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.8b06859

  日期：2019.2.27

  Plant viral diseases seriously affect crop yield and quality. The natural product gramine (1) and its simple structural analogues 2-35 were synthesized from indoles, amines, and aldehydes in one step. The antiviral effects of these alkaloids were evaluated systematically. Most of these compounds were found to have higher antiviral effects than commercial ribavirin for the first time. Especially compounds 22, 30, and 31 exhibited significantly higher effects than ningnanmycin, thereby emerging as novel antiviral leads for further optimization. The preliminary implementation indicated that these compounds likely inhibit the assembly of tobacco mosaic virus (TMV) by cross-linking TMV capsid protein. Gramine analogues were also found to have broad-spectrum fungicidal effects. Although gramine has been reported to have influence on germination and development of Erysiphe graminis, these compounds displayed no fungicidal effects against Blumeria graminis f. sp. tritici on wheat in our test. Some of these compounds also exhibited certain insecticidal activities.
• Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction
  作者：U. Chinna Rajesh、Rohit Kholiya、V. Satya Pavan、Diwan S. Rawat

  DOI：10.1016/j.tetlet.2014.03.112

  日期：2014.4

  A highly efficient and sustainable approach for the multi-component synthesis of biologically important 3-amino alkylated indoles has been investigated via Mannich-type reaction under catalyst-free, ethylene glycol as a recyclable promoting medium. The wide applicability of the present method was examined with various substrates viz substituted aldehydes, indoles and secondary amines. This method will be useful for a large scale synthesis of 3-amino alkylated indoles without the use of column chromatography. The present method provides higher environmental compatibility and sustainability factors such as smaller E-factor (0.433) and higher atom-economy (AE = 93.3%). (C) 2014 Elsevier Ltd. All rights reserved.
• Iron mediated one pot three component synthesis of 3-substituted indoles via aerobic iminium ion formation
  作者：Vinay K. Singh、Laxmi Kant Sharma、Rana Krishna Pal Singh

  DOI：10.1016/j.tetlet.2015.12.047

  日期：2016.1

  An efficient and economical method was developed for the synthesis of 3 substituted indoles by a highly efficient one-pot three component coupling reaction of substituted or unsubstituted benzyl alcohol, N-methyl aniline or pyrrolidine, and indoles or substituted indoles. (C) 2015 Published by Elsevier Ltd.