(4-((1H-indol-3-yl)methyl)piperazin-1-yl)(furan-2-yl)methanone | 383149-20-0

• 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: (4-((1H-indol-3-yl)methyl)piperazin-1-yl)(furan-2-yl)methanone
• 英文别名: 3-{[4-(2-furoyl)piperazin-1-yl]methyl}-1H-indole；2-furyl[4-(1H-indol-3-ylmethyl)-1-piperazinyl]methanone；furan-2-yl[4-(1H-indol-3-ylmethyl)piperazin-1-yl]methanone；furan-2-yl-[4-(1H-indol-3-ylmethyl)piperazin-1-yl]methanone
• CAS: 383149-20-0
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: HZDVQZKEWSXXOR-UHFFFAOYSA-N

物化性质

• 沸点：
  514.4±50.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 聚合甲醛 、 1-(2-糠酰)哌嗪 以 甲醇 为溶剂， 反应 0.08h， 以42%的产率得到(4-((1H-indol-3-yl)methyl)piperazin-1-yl)(furan-2-yl)methanone
  参考文献：
  名称：

  新型曼尼希碱3-取代吲哚衍生物的合成与表征

  摘要：

  本研究通过微波辅助合成曼尼希反应和常规回流加热方法合成了10种吲哚核3位3位取代的吲哚衍生物。微波辅助合成比回流法更优选，因为微波辐射导致更高的产物收率、更好的纯度以及提高的能量效率和缩短的反应时间。通过FT-IR、元素分析、1H NMR和13C NMR光谱对3-取代吲哚衍生物的结构进行了表征

  DOI：

  10.14233/ajchem.2021.23035

文献信息

• Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida, Journal of the Chemical Society of Pakistan, 2012, vol. 34, # 3, p. 748 - 757
  作者：Khan, Khalid Mohammed、Rahim, Fazal、Ambreen, Nida、Taha, Muhammad、Iqbal, Sarosh、Haider, Syed Moazzam、Perveen, Shahnaz

  DOI：——

  日期：——
• Synthetic indole Mannich bases: Their ability to modulate in vitro cellular immunity
  作者：M. Ahmed Mesaik、Khalid Mohammed Khan、Fazal Rahim、Muhammad Taha、Syed Moazzam Haider、Shahnaz Perveen、Ahmed Shukralla Khalid、Omer M. Abdalla、Samreen Soomro、Wolfgang Voelter

  DOI：10.1016/j.bioorg.2015.05.003

  日期：2015.6

  The synthetic indole Mannich bases 1-13 have been investigated for their ability to modulate immune responses measured in vitro. These activities were based on monitoring their affects on T-lymphocyte proliferation, reactive oxygen species (ROS), IL (interleukin)-2, IL-4, and nitric oxide production. Compound 5 was found to be the most potent immunomodulator in this context. Four of the synthesized compounds, 5, 11, 12, and 13, have significant potent inhibitory effects on T-cell proliferation, IL-4, and nitric oxide production. However, none of the thirteen indole compounds exerted any activity against ROS production. (C) 2015 Elsevier Inc. All rights reserved.
• Synthesis and Characterization of 3-Substituted Indole Derivatives as Novel Mannich Bases
  作者：E. Erdag

  DOI：10.14233/ajchem.2021.23035

  日期：2021.3.31

  In this study, ten 3-substituted indole derivatives at the 3rd position of indole nucleus were synthesized via Mannich reaction with microwave assisted synthesis and the conventional reflux heating method. Microwave assisted synthesis is more preferrable than reflux method since the microwave irradiation lead to a higher product yields with better purity and improved energy efficiency with shortened

  本研究通过微波辅助合成曼尼希反应和常规回流加热方法合成了10种吲哚核3位3位取代的吲哚衍生物。微波辅助合成比回流法更优选，因为微波辐射导致更高的产物收率、更好的纯度以及提高的能量效率和缩短的反应时间。通过FT-IR、元素分析、1H NMR和13C NMR光谱对3-取代吲哚衍生物的结构进行了表征