4-(3-nitrophenyl)-2H-chromen-2-one | 1092835-47-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(3-nitrophenyl)-2H-chromen-2-one
• 英文别名: 4-(3-Nitrophenyl)chromen-2-one
• CAS: 1092835-47-6
• 化学式: C₁₅H₉NO₄
• 分子量: 267.241
• InChiKey: WUSKEVLNQYTHME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-羟基香豆素 、 3-硝基苯硼酸 在 sodium carbonate 、 对甲苯磺酰氯 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 以68%的产率得到4-(3-nitrophenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Palladium-catalyzed direct arylation of 4-hydroxycoumarins with arylboronic acids via C–OH bond activation

  摘要：

  Operationally simple PdCl2-Catalyzed direct arylation of 4-hydroxycoumarins with arylboronic acids via C-OH bond activation under mild conditions is described, which gave rise to the corresponding 4-arylcoumarins in good to excellent yields. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.116

文献信息

• Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts
  作者：Yang Yang、Jianwei Han、Xunshen Wu、Shujia Xu、Limin Wang

  DOI：10.1016/j.tetlet.2015.04.082

  日期：2015.6

  ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions. Additionally, this protocol provided an efficient alternative for the preparation of related 4-arylated coumarin compounds which are useful in the access to 5-lipoxygenase inhibitors.

  已经开发了使用二芳基碘鎓（III）盐的钯催化的邻羟基肉桂酸酯衍生物的芳基化/环化反应。用这种方法，可以容易地在无碱条件下以良好的产率制备4-芳基香豆素。另外，该方案为制备相关的4-芳基香豆素化合物提供了有效的替代方法，该化合物可用于获得5-脂氧合酶抑制剂。
• Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
  作者：Yoshihiko Yamamoto、Naohiro Kirai

  DOI：10.1021/ol802239n

  日期：2008.12.18

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.