6-hydroxy-3-nitrocoumarin | 158521-86-9

• 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: 6-hydroxy-3-nitrocoumarin
• 英文别名: 6-Hydroxy-3-nitrochromen-2-one
• CAS: 158521-86-9
• 化学式: C₉H₅NO₅
• 分子量: 207.142
• InChiKey: GYCMERREXDAHAG-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C(Solv: ethanol (64-17-5))
• 沸点：
  457.8±45.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：

  三氟甲磺酸异丙酯 、 6-hydroxy-3-nitrocoumarin 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 6-Isopropoxy-3-nitro-chromen-2-one
  参考文献：
  名称：

  Phospholipase C Inhibitors: A New Class of Agents

  摘要：

  A series of nitrocoumarin and nitrochromene derivatives have been prepared and shown to inhibit the phosphatidylinositol-specific phospholipase C(PLC)(IC50 < 10 mu g/mL) isolated from human melanoma. The inhibition of PLC by nitrocoumarin 4a was time-dependent and irreversible. The inhibition of PLC was shown to interfere with inositide metabolism in whole cells (IC50 = 4 mu g/mL) in a manner consistent with their proposed mode of activity, Finally, the compounds were shown to be growth inhibitory to cultured melanoma cells (ID50 = 2 mu g/ML), suggesting that PLC may be an attractive new target for chemotherapeutic intervention.

  DOI：

  10.1021/jm00040a016
• 作为产物：
  描述：

  硝基乙酸乙酯 、 2,5-二羟基苯甲醛 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以75%的产率得到6-hydroxy-3-nitrocoumarin
  参考文献：
  名称：

  l -Proline catalyzed condensation of salicylaldehydes with ethyl nitroacetate: an efficient access to 3-nitrocoumarins

  摘要：

  Abstractl-Proline catalyzed condensation of salicylaldehydes and ethyl nitroacetate afforded 3-nitrocoumarins in good to high yields under mild conditions. This organocatalyzed process offers a much improved yield of 3-nitrocoumarins and well tolerates both electron-donating and electron-withdrawing substituents on the phenyl ring. Graphical abstract

  DOI：

  10.1007/s00706-016-1736-4

文献信息

• 3-Nitrocoumarins as Dienophiles in the Diels−Alder Reaction in Water. An Approach to the Synthesis of Nitrotetrahydrobenzo[<i>c</i>]chromenones and Dihydrodibenzo[<i>b</i>,<i>d</i>]furans
  作者：David Amantini、Francesco Fringuelli、Oriana Piermatti、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo034956e

  日期：2003.11.1

  cyclopentadiene (12) were investigated in aqueous medium, in organic solvent and under solventless conditions. The reactions performed in water occurred in heterogeneous phase but were faster than those executed in toluene or dichloroethane (DCE). 1a-c, 5, and 6 behaved as 2pi components in the Diels-Alder cycloadditions with 7-10 and 12, and exo adducts were preferentially or exclusively produced. Surprisingly

  3-硝基香豆素（1a），6-氯-3-硝基香豆素（1b）和6-，7-和8-羟基-3-硝基香豆素（1c，5和6）的[4 + 2]环加成（E）-戊二烯（7），异戊二烯（8），2,3-二甲基-1,3-丁二烯（9），2-甲氧基-1,3-丁二烯（10），2,3-二甲氧基-1，在水性介质中，有机溶剂中和无溶剂条件下研究了3-丁二烯（11）和环戊二烯（12）。在水中进行的反应发生在异相中，但比在甲苯或二氯乙烷（DCE）中进行的反应要快。在Diels-Alder环加成7-10和12中，1a-c，5和6表现为2pi成分，并且优先或专门生产exo加成物。出乎意料的是，1a在水中的环加成中表现为4pi成分，分离出11和4-取代的3-硝基苯并二氢吡喃酮20和21。羟基-3-硝基香豆素1c，5和6与1,3-二烯9的环加成反应在水或有机溶剂中不起作用，但在无溶剂条件下起作用。源自正常电子需求Diels-Alder反应的
• Uncatalyzed [4 + 2] Cycloadditions of 3-Nitrocoumarins with Vinyl Ethers in Solventless Conditions. A New Entry to Chromene Derivatives
  作者：David Amantini、Francesco Fringuelli、Ferdinando Pizzo

  DOI：10.1021/jo0260185

  日期：2002.10.1

  (ethyl vinyl ether (8), 2,3-dihydrofuran (9), and 3,4-dihydro-2H-pyran (10)) were investigated in water, in neat conditions, and in organic solvents. The cycloadditions do not require the use of catalysts and are highly endo diastereoselective, and in water the cyclic nitronates 13, 18, and 23 are converted into chromene derivatives via hydrolysis, decarboxylation, and acetalation reactions. A one-pot

  研究了3-硝基香豆素5与富电子的亲双烯体（乙基乙烯基醚（8），2,3-二氢呋喃（9）和3,4-二氢-2H-吡喃（10））的[4 + 2]环加成反应。在水，纯净条件和有机溶剂中。环加成不需要使用催化剂，并且对内非对映选择性高，并且在水中，环状硝酸酯13、18和23通过水解，脱羧和缩醛化反应转化为亚甲基苯衍生物。基于在纯净/水条件下的连续反应的一锅法程序可将3-硝基香豆素5用作合成色酚，四氢呋喃-和四氢吡喃并色酮的结构单元。首次研究了将1,2-恶嗪环的CO键作为缩醛的一部分的环状硝酸酯的水解。
• Compositions and methods for enhancing paracellular permeability across epithelial and endothelial barriers
  申请人：——

  公开号：US20020115641A1

  公开（公告）日：2002-08-22

  Compositions and methods for enhancing paracellular permeability at an absorption site in a subject are disclosed. The method includes: (a) administering an effective amount of a phospholipase C inhibitor to a subject at a time in which enhanced paracellular permeability is desired; and (b) enhancing paracellular permeability in the subject at the absorption site through the administering of the effective amount of the phospholipase C inhibitor. The disclosed compositions and methods provide enhanced absorption of a hydrophilic drug in a subject.

  本发明公开了用于增强受试者吸收部位旁细胞渗透性的组合物和方法。该方法包括(a) 在需要增强细胞旁通透性时，向受试者施用有效量的磷脂酶 C 抑制剂；以及 (b) 通过施用有效量的磷脂酶 C 抑制剂，增强受试者吸收部位的细胞旁通透性。所公开的组合物和方法可增强受试者对亲水性药物的吸收。
• Perrella Frank W., Chen Shih-Fong, Behrens Davette L., Kaltenbach Robert +, J. Med. Chem, 37 (1994) N 14, S 2232-2237
  作者：Perrella Frank W., Chen Shih-Fong, Behrens Davette L., Kaltenbach Robert +

  DOI：——

  日期：——
• COMPOSITIONS AND METHODS FOR ENHANCING PARACELLULAR PERMEABILITY ACROSS EPITHELIAL AND ENDOTHELIAL BARRIERS
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1379235B1

  公开（公告）日：2006-12-20