2H-1-苯并吡喃-2-酮,7-羟基-6-硝基- | 112212-20-1

• 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
• 中文名称: 2H-1-苯并吡喃-2-酮,7-羟基-6-硝基-
• 英文名称: 7-hydroxy-6-nitrocoumarin
• 英文别名: 6-nitro-7-hydroxycoumarin；7-hydroxy-6-nitrochromen-2-one
• CAS: 112212-20-1
• 化学式: C₉H₅NO₅
• 分子量: 207.142
• InChiKey: FYTIEXBLBZJANI-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  414.9±45.0 °C(Predicted)
• 密度：
  1.626±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2H-1-苯并吡喃-2-酮,7-羟基-6-硝基- 生成 7-acetoxy-6-nitro-coumarin
  参考文献：
  名称：

  Chakravarti; Ghosh, Journal of the Indian Chemical Society, 1935, vol. 12, p. 793

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基香豆素 在 5-methyl-1,4-dinitro-1H-imidazole 作用下， 以 乙腈 为溶剂， 以55%的产率得到2H-1-苯并吡喃-2-酮,7-羟基-6-硝基-
  参考文献：
  名称：

  蛋白质的光控酪氨酸硝化

  摘要：

  蛋白质的酪氨酸硝化是体内最重要的氧化翻译后修饰之一。其生化和生理研究的一个主要障碍是缺乏有效和化学选择性的蛋白质酪氨酸硝化试剂。在此，我们报告了一种通过使用生物相容性二硝基咪唑试剂进行光控蛋白质酪氨酸硝化的通用策略。在 390 nm 照射下，二硝基咪唑在中性水性缓冲液条件下以快速动力学和高化学选择性将肽和蛋白质中的酪氨酸残基有效转化为 3-硝基酪氨酸残基。3-硝基酪氨酸残基的掺入增强了套索肽天然产物的热稳定性，并赋予鼠肿瘤坏死因子-α强大的免疫原性以打破自身耐受。

  DOI：

  10.1002/anie.202102287

文献信息

• Highly efficient nitration of phenolic compounds by zirconyl nitrate
  作者：J. Jon Paul Selvam、V. Suresh、K. Rajesh、S. Ravinder Reddy、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.02.057

  日期：2006.4

  Zirconyl nitrate was found to be an excellent reagent in the nitration of phenol and substituted phenols to give nitrated phenols. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity.

  发现硝酸氧锆是在苯酚和取代的苯酚的硝化中得到硝化的苯酚的极好试剂。该方法在室温下对大多数实施例有效地进行，以高的区域选择性以中等至良好的产率产生硝基衍生物。
• CERIUM(IV) AMMONIUM NITRATE MEDIATED NITRATION OF COUMARINS
  作者：N. Ganguly、A. K. Sukai、S. De

  DOI：10.1081/scc-100000214

  日期：2001.1

  A new convenient method of nitration of coumarins using cerium(IV) ammonium nitrate (CAN) has been developed. Higher regioselectivity is observed with CAN and hydrogen peroxide in aqueous medium in comparison with CAN in acetic acid for nitration of 7-hydroxycoumarin, 7-hydroxy-4-methyl coumarin and their derivatives.

  已经开发了一种使用硝酸铈 (IV) 铵 (CAN) 硝化香豆素的新方法。与乙酸中的 CAN 相比，CAN 和过氧化氢在水性介质中对 7-羟基香豆素、7-羟基-4-甲基香豆素及其衍生物的硝化具有更高的区域选择性。
• REGIOSELECTIVE MONONITRATION OF COUMARINS USING CHROMIUM NITRATE AS NITRATING AGENT
  作者：Vandana Bansal、R. N. Khanna

  DOI：10.1081/scc-120003630

  日期：2002.1

  ABSTRACT A very efficient and simple method is presented for the regioselective mononitration of coumarins, using chromium nitrate in acetic anhydride, in high yields at room temperature.

  摘要提出了一种非常有效和简单的方法，用于香豆素的区域选择性单硝化，使用醋酸酐中的硝酸铬，在室温下以高产率进行。
• Synthesis of Fused Oxazolocoumarins from <i>o</i> -Hydroxynitrocoumarins and Benzyl Alcohol Under Gold Nanoparticles or FeCl₃ Catalysis
  作者：Evangelia-Eirini N. Vlachou、Gerasimos S. Armatas、Konstantinos E. Litinas

  DOI：10.1002/jhet.2842

  日期：2017.7

  Synthesis of fused oxazolocoumarins has been achieved from the one‐pot tandem reactions of o‐hydroxynitrocoumarins with benzyl alcohol in toluene under catalysis in a sealed tube at 150°C. The catalysis was performed by gold nanoparticles supported on TiO2 (0.4 mol% Au) or FeCl3 (5%) or silver nanoparticles supported on TiO2 (1.7 mol% Ag).

  邻羟基硝基香豆素与苯甲醇在甲苯中在150°C的密闭管催化下的单锅串联反应可实现稠合的恶唑香豆素的合成。通过负载在TiO 2（0.4 mol％Au）或FeCl 3（5％）上的金纳米颗粒或负载在TiO 2（1.7 mol％Ag）上的银纳米颗粒进行催化。
• Dual 5-HT1A agonists and 5-HT re-uptake inhibitors by combination of indole-butyl-amine and chromenonyl-piperazine structural elements in a single molecular entity
  作者：Timo Heinrich、Henning Böttcher、Kai Schiemann、Günter Hölzemann、Michael Schwarz、Gerd D. Bartoszyk、Christoph van Amsterdam、Hartmut E. Greiner、Christoph A. Seyfried

  DOI：10.1016/j.bmc.2004.07.014

  日期：2004.9

  The dual serotonin (5-HT) re-uptake inhibitor and 5-HT1A receptor agonist vilazodone was found to increase central serotonin levels in rat brain. In the course of structural modifications of vilazodone 3-4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]-butyl}-1H-indole-5-carbonitrile 8i and its fluorine analogue 6-4-[4-(5-fluor-3-indolyl)-butyl]-1-piperazinyl}-2H-1-benzopyran-2-one have been identified. These unsubstituted chromenones are equally potent at the 5-HT1A receptor and 5-HT transporter. The implementation of nitrogen functionalities in position 3 of the chromenones resulted in compounds acting as agonists at the 5-HT1A receptor and as 5-HT re-uptake inhibitors like vilazodone. Ex vivo 5-HT re-uptake inhibition and in vitro 5-HT agonism were determined in the PCA- and GTRgammaS-assay, respectively. The potential of these chromenones to increase central 5-HT levels was measured in microdialysis studies and especially the derivatives 3-4-[4-(3-amino-2-oxo-2H-chromen-6-yl)-piperazin-1-yl]-butyl-1H-indole-5-carbonitrile 8f, ethyl (6-4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-carbamate 8h and N-(6-4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-2-oxo-2H-chromen-3-yl)-acetamide 8k give rise to rapid development of increased serotonin levels in rat brain cortex, lasting longer than 3h. (C) 2004 Elsevier Ltd. All rights reserved.