4-methyl-7-nitro-2H-chromen-2-one | 179897-88-2

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 4-methyl-7-nitro-2H-chromen-2-one
• 英文别名: 4-methyl-7-nitrocoumarin；7-nitro-4-methylcoumarin；4-methyl-7-nitrochromen-2-one
• CAS: 179897-88-2
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: OGFCYRNIJNJKBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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

• 作为反应物：
  描述：

  4-methyl-7-nitro-2H-chromen-2-one 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 以10%的产率得到2-isopropenyl-5-nitrophenol
  参考文献：
  名称：

  Ethylene glycol as hydrogen donor for the syntheses of thymol analogues via hydrolysis of 4-methylcoumarins

  摘要：

  Treatment of 4-methylcoumarins with potassium hydroxide in ethylene glycol resulted in the formation of the 'normal' 2-isopropenylphenols and/or the 'abnormal' 2-isopropylphenols depending on the nature of the substrates. The solvent ethylene glycol was believed to be the hydrogen donor for double-bonding reduction where 2-isopropylphenol was produced. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.122
• 作为产物：
  描述：

  间硝基苯酚 、 乙酰乙酸乙酯 在 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium chloride immobilized on micro/mesoporous HY zeolite 作用下， 以 neat (no solvent) 为溶剂， 反应 2.5h， 以82%的产率得到4-methyl-7-nitro-2H-chromen-2-one
  参考文献：
  名称：

  固定在沸石上的离子液体：通过Pechmann反应合成香豆素的表征和催化活性

  摘要：

  在这项工作中，第一步是将1-甲基-3-（3-三甲氧基甲硅烷基丙基）咪唑鎓氯化物（[MTMSPIm] Cl）固定在HY和NaY沸石上作为酸性催化剂。通过不同的方法如FTIR，TGA，XRD，BET，SEM，EDX和ICP对合成的催化剂进行了很好的表征。催化剂的表征确实显示了负载在胺官能化沸石上的离子液体。同样，结果显示出催化剂的微/介孔结构已经作为一类重要的催化材料出现。微/介催化剂（[MTMSPIm] Cl @沸石）用作酸性催化剂，可在无溶剂条件下通过Pechmann反应合成香豆素。研究了催化剂用量，溶剂和时间等不同因素的影响。最后，催化剂可以很容易地分离出来，并至少在五个反应中再用于下一步反应，而催化剂的收率和结构没有任何重大变化。改性沸石与[MTMSPIm] Cl的比较显示出较高的收率和选择性，且温和的条件与其他工作有关。

  DOI：

  10.1007/s13738-020-01950-x

文献信息

• Ytterbium triflate promoted coupling of phenols and propiolic acids: synthesis of coumarins
  作者：Serena Fiorito、Francesco Epifano、Vito A. Taddeo、Salvatore Genovese

  DOI：10.1016/j.tetlet.2016.05.087

  日期：2016.6

  Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols

  香豆素是众所周知的天然和半合成产品，具有重要的有效药理活性。在这封信中，描述了一种化学合成这类化合物的改进方法。在10％的Yb（OTf）3水合物作为催化剂存在下，在短时间内从微波辐射和无溶剂条件下，短短地从不同取代的酚和丙酸作为起始原料，以良好的产率获得了香豆素。
• Steroid receptor modulator compounds and methods
  申请人：——

  公开号：US20040186132A1

  公开（公告）日：2004-09-23

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  本文披露了高亲和力、高选择性的非类固醇化合物，可作为类固醇受体调节剂。同时也披露了包含这些化合物的药物组合物，以及使用这些化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法，还包括制备这些化合物的中间体和制备类固醇受体调节剂化合物的方法。
• Methods for the preparation of coumarine derivatives
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1041071A1

  公开（公告）日：2000-10-04

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  本发明公开了对类固醇受体具有高亲和力、高选择性调节作用的非类固醇化合物。还公开了含有此类化合物的药物组合物、使用所公开化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法、制备化合物时有用的中间体以及制备类固醇受体调节剂化合物的工艺。
• Nitrocoumarins for detecting all micro-organisms
  申请人：——

  公开号：US20020031795A1

  公开（公告）日：2002-03-14

  This invention concerns a compound for detecting the presence or absence of at least one microorganism. The invention also concerns the use of a compound in a detection and/or diagnostic test. The said invention further concerns a method for detecting nitroaryl reductase activity in a bacteria culture medium. Finally, the invention concerns the use of such a compound, methods for isolating and detecting microorganisms or a group of microorganisms in a sample likely to contain them, and various applications thereof. The invention is characterized in that the compound consist of a nitrocoumarin molecule or one of its derivatives, which is fluorescent in reduced state. The invention is particularly applicable in the field of diagnosis.

  本发明涉及一种用于检测是否存在至少一种微生物的化合物。本发明还涉及一种化合物在检测和/或诊断试验中的用途。本发明还涉及一种检测细菌培养基中硝基芳香还原酶活性的方法。最后，本发明涉及这种化合物的用途、在可能含有微生物的样品中分离和检测微生物或微生物群的方法及其各种应用。 本发明的特征在于，该化合物由硝基香豆素分子或其衍生物之一组成，在还原状态下具有荧光性。 本发明尤其适用于诊断领域。
• CuFe₂O₄ Nanoparticles: A Magnetically Recoverable and Reusable Catalyst for the Synthesis of Coumarins via Pechmann Reaction in Water
  作者：Seyed Meysam Baghbanian、Maryam Farhang

  DOI：10.1080/00397911.2013.835423

  日期：2014.3.4

  The synthesis of coumarins by hydroxyalkylation of phenols with ethyl acetoacetate (via Pechmann reaction) is attempted using magnetically separable and reusable CuFe2O4 nanoparticles in water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications((R)) for the following free supplemental resource(s): Full experimental and spectral details.]