8-nitro-4-methylcoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-nitro-4-methylcoumarin
• 英文别名: 4-methyl-8-nitrochromen-2-one
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: ZHRWYUMUJKDWQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 硝苯酚 在 1,1'-butylenebispyridinium hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.58h， 以91%的产率得到8-nitro-4-methylcoumarin
  参考文献：
  名称：

  硫酸亚丁基双吡啶鎓一锅法合成香豆碱衍生物

  摘要：

  3-羟基苯酚与乙酰乙酸乙酯的Pechmann缩合反应在1,1'-丁烯双吡啶硫酸氢盐存在下作为高效，绿色且可回收的催化剂在室温下无溶剂条件下以良好的收率生产7-羟基-4-甲基香豆素。该催化剂具有以下优点：良好至优异的产率，短的反应时间，操作简单和后处理程序容易。

  DOI：

  10.1007/s11164-015-2261-5

文献信息

• One-pot synthesis of coumarine derivatives using butylenebispyridinium hydrogen sulfate as novel ionic liquid catalyst
  作者：Sobhan Rezayati、Fatemeh Sheikholeslami-Farahani、Faramarz Rostami-Charati、Saeid Afshari Sharif Abad

  DOI：10.1007/s11164-015-2261-5

  日期：2016.5

  reaction of 3-hydroxyphenol and ethyl acetoacetate in the presence of 1,1′‐butylenebispyridinium hydrogen sulfate as an efficient, green, and recyclable catalyst produces 7-hydroxy-4-methylcoumarin in good yield under solvent-free conditions at room temperature. This catalyst has advantages such as the following: good to excellent yields, short reaction times, simplicity in operation, and easy workup procedure

  3-羟基苯酚与乙酰乙酸乙酯的Pechmann缩合反应在1,1'-丁烯双吡啶硫酸氢盐存在下作为高效，绿色且可回收的催化剂在室温下无溶剂条件下以良好的收率生产7-羟基-4-甲基香豆素。该催化剂具有以下优点：良好至优异的产率，短的反应时间，操作简单和后处理程序容易。
• Coumarins: Facile and Expeditious Synthesis<i>via</i>Keggin-Type Heteropolycompounds under Solvent-Free Condition
  作者：Ezzat Rafiee、Akram Fakhri、Mohammad Joshaghani

  DOI：10.1002/jhet.621

  日期：2013.8

  Different Keggin‐type heteropolycompounds were used in Pechmann reaction to obtain biologically active coumarins. Effect of solvent, catalyst loading, and molar ratios of substrates was studied to introduce the best reaction condition. The optimized reaction condition was extended to Pechmann reaction of methylacetoacetate with various monohydric and polyhydric phenols. This rapid procedure afforded

  Pechmann反应中使用了不同的Keggin型杂多化合物来获得具有生物活性的香豆素。研究了溶剂，催化剂用量和底物摩尔比的影响，以引入最佳反应条件。优化的反应条件扩展到乙酰乙酸甲酯与各种一元和多元酚的Pechmann反应。这种快速的过程提供了结构多样的香豆素，具有高到极好的收率。该方法的优点是反应时间短，操作简单，反应条件温和。优化的催化剂可重复使用四次。
• Tetrakis(acetonitrile)copper(I) hexafluorophosphate catalyzed coumarin synthesis via pechmann condensation under solvent-free condition
  作者：Ebrahim Soleimani、Mohammad Mehdi Khodaei、Nasim Batooie、Saadi Samadi

  DOI：10.1002/jhet.814

  日期：2012.3

  Tetrakis(acetonitrile)copper(I) hexafluorophosphate (Cu(CH3CN)4PF6) is used as an efficient catalyst in the Pechmann condensation reaction of phenols with ethyl acetoacetate leading to the formation of coumarin derivatives in excellent yields under solvent free conditions at ambient temperature. The method is simple, solvent‐free and gives excellent yields in a short reaction time. J. Heterocyclic

  四（乙腈）铜（I）六氟磷酸酯（ Cu（CH 3 CN）4 PF 6）在酚与乙酰乙酸乙酯的Pechmann缩合反应中用作有效的催化剂，导致在无溶剂条件下以优异的产率形成香豆素衍生物在环境温度下。该方法简单，无溶剂，并且在较短的反应时间内即可获得出色的收率。J.杂环化​​学。，（2011）。
• Samarium(III) catalyzed one-pot construction of coumarins
  作者：Sushilkumar S. Bahekar、Devanand B. Shinde

  DOI：10.1016/j.tetlet.2004.09.013

  日期：2004.10

  Samarium(III) nitrate hexahydrate as a catalyst is used as an alternative to conventional acid catalysts in the von Pechmann condensation of phenols with ethyl acetoacetate leading to the formation of coumarin derivatives.

  六水合硝酸nitrate（III）用作苯酚与乙酰乙酸乙酯在von Pechmann缩合反应中形成香豆素衍生物的常规酸催化剂的替代品。
• Zinc mediated transesterification of β-ketoesters and coumarin synthesis
  作者：Subhash P Chavan、K Shivasankar、R Sivappa、Ramesh Kale

  DOI：10.1016/s0040-4039(02)02006-3

  日期：2002.11

  The transesterification of ketoesters using zinc and iodine is described. The reaction has been done on a variety of alcohols and phenols. Alcohols furnish transesterified products whereas phenols gave 4-methylcoumarins. The method is highly promising compared with existing methods. (C) 2002 Elsevier Science Ltd. All rights reserved.