4-hydroxy-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one | 1508266-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-Hydroxy-2-(4-nitrophenyl)-2,3-dihydropyran-6-one；4-hydroxy-2-(4-nitrophenyl)-2,3-dihydropyran-6-one
• CAS: 1508266-53-2
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: UUZIEHREQPXUNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-3-(4-硝基苯基)丙酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 以504 mg的产率得到4-hydroxy-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction

  摘要：

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.079

文献信息

• A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction
  作者：Masahiro Mineno、Yasuhiro Sawai、Kazuaki Kanno、Naotaka Sawada、Hideya Mizufune

  DOI：10.1016/j.tet.2013.10.079

  日期：2013.12

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.