5-methoxy-3-(4-methoxyphenylmethyl)indole | 138469-75-7

• 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: 5-methoxy-3-(4-methoxyphenylmethyl)indole
• 英文别名: 5-methoxy-3-(4-methoxybenzyl)-1H-indole；5-methoxy-3-[(4-methoxyphenyl)methyl]-1H-indole
• CAS: 138469-75-7
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: SMUFELBAVIFGIR-UHFFFAOYSA-N

物化性质

• 沸点：
  453.3±35.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (5-甲氧基-2-硝基苯基)乙腈 在 palladium on activated charcoal 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 正丁醇 为溶剂， 生成 5-methoxy-3-(4-methoxyphenylmethyl)indole
  参考文献：
  名称：

  The use of o-nitroarylacetonitriles as carbon acid participants in the mitsunobu reaction

  摘要：

  The use of o-nitroarylacetonitriles as carbon acids in the Mitsunobu reaction is discussed as a method of carbon-carbon bond formation. This reaction represents a rare example of a carbon acid participating in a Mitsunobu reaction.

  DOI：

  10.1016/0040-4039(91)80474-k

文献信息

• Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols
  作者：Avijit Mondal、Rahul Sharma、Bishal Dutta、Debjyoti Pal、Dipankar Srimani

  DOI：10.1021/acs.joc.1c02702

  日期：2022.3.18

  Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates

  在此，我们展示了 Mn 催化的吲哚与醇的选择性 C-3 官能化。开发的催化剂还可以在稍微改进的反应条件下从同一组底物提供双（吲哚基）甲烷。机理研究表明，吲哚的 C-3 官能化是通过借氢途径进行的。为了突出实用性，合成了多种底物，包括九种结构上重要的药物分子。此外，我们还介绍了一种一锅级联策略，用于直接从 2-氨基苯基乙醇和酒精合成 C-3 官能化吲哚。
• Visible light mediated Iron-Catalyzed synthesis of C-3 alkylated Indoles, bisindolylmethanes and flavanones using alcohols
  作者：Mohd Waheed、Meshari A Alsharif、Mohammed Issa Alahmdi、Sayeed Mukhtar、Humaira Parveen

  DOI：10.1016/j.tetlet.2023.154428

  日期：2023.4

  benign, mild approach for synthesis of C-3 alkylated indoles, bisindolylmethanes and flavanones using alcohols at room temperature under visible light has been developed. The reported reaction conditions were favorable for a wide range of alcohols afforded good to excellent yields of the respective products. Additionally, the reaction system was successfully extended to the synthesis of flavanones from

  开发了一种在室温下可见光下使用醇类合成 C-3 烷基化吲哚、双吲哚基甲烷和黄烷酮的环境友好、温和的方法。所报告的反应条件有利于各种醇，从而提供了各自产品的良好至极佳收率。此外，该反应体系成功扩展到由2-羟基苯乙酮合成黄烷酮。低成本和空气稳定的 Knölker 铁催化剂已被用于通常需要较高温度的光解下醇的脱氢。
• Oxygen Dependent Switchable Selectivity during Ruthenium Catalyzed Selective Synthesis of <i>C3</i>-Alkylated Indoles and Bis(indolyl)methanes
  作者：Amit Kumar Guin、Subhasree Pal、Subhajit Chakraborty、Santana Chakraborty、Nanda D. Paul

  DOI：10.1021/acs.joc.3c01191

  日期：2023.12.15

  redox-controlled oxygen-dependent switchable selectivity during ruthenium-catalyzed selective synthesis of C3-alkylated indoles and bis(indolyl)methanes (BIMs). A wide variety of C3-alkylated indoles and BIMs were prepared selectively in moderate to good isolated yields by coupling a wide variety of indoles and alcohols, catalyzed by a well-defined, air-stable, and easy-to-prepare Ru(II)-catalyst (1a)

  在此，我们报道了在钌催化选择性合成C3烷基化吲哚和双（吲哚基）甲烷（BIM）过程中以配体为中心的氧化还原控制的氧依赖性可切换选择性。在结构明确、空气稳定且易于制备的 Ru(II) 催化下，通过偶联多种吲哚和醇，以中等至良好的分离收率选择性地制备多种C3烷基化吲哚和 BIM -带有氧化还原活性三齿钳（ L 1a ）的催化剂（ 1a ）。催化剂1a在氩气气氛下有效催化吲哚的C3烷基化，同时在氧气环境下专门产生BIM。一些含有 BIM 的药物分子也被有效合成。 1a对含有内部碳-碳双键的醇表现出优异的化学选择性。机理研究表明，配位偶氮芳香配体在催化过程中积极参与。在醇脱氢过程中，配体的偶氮部分储存从醇中除去的氢，随后将氢转移至亚烷基吲哚中间体，形成C3烷基化吲哚。而在氧气环境下，氢从配体支架转移到分子氧会产生H 2 O 2 ，​​不给亚烷基假吲哚中间体的氢化留下余地，而不是进行1,4-迈克尔型加成形成BIM。
• Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols
  作者：Xue-Qiang Chu、Ran Jiang、Yi Fang、Zheng-Yang Gu、Hua Meng、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.045

  日期：2013.1

  A series of HSO4- functionalized ILs was synthesized and used as efficient, green, and metal-free catalysts for benzylation. Notably, the catalytic system has wide substrate scopes and the ionic liquid catalysts were applied to investigate three different types of nucleophiles to give the desired benzylation products with moderate to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
• The use of o-nitroarylacetonitriles as carbon acid participants in the mitsunobu reaction
  作者：John E. Macor、Jennifer M. Wehner

  DOI：10.1016/0040-4039(91)80474-k

  日期：1991.12

  The use of o-nitroarylacetonitriles as carbon acids in the Mitsunobu reaction is discussed as a method of carbon-carbon bond formation. This reaction represents a rare example of a carbon acid participating in a Mitsunobu reaction.