4-hydroxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one | 62378-62-5

• 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-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-Hydroxy-6-(1-trans-styryl)-5,6-dehydro-2-pyron；4-Hydroxy-6-styryl-5,6-dihydro-pyran-2-one；4-hydroxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
• CAS: 62378-62-5
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: GAEBQUJLHSUKEK-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 kawain
  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
• 作为产物：
  描述：

  (E)-ethyl 3-hydroxy-5-phenylpent-4-enoate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 以370.3 mg的产率得到4-hydroxy-6-[(E)-2-phenylethenyl]-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

• Biomimetic iterative method for polyketide synthesis
  作者：Kengo Akagawa、Kazuaki Kudo

  DOI：10.1039/c7cc04033d

  日期：——

  iterative method for synthesizing polyketides was demonstrated, in which the chain elongation of a carboxylic acid was performed by decarboxylative dehydration condensation with a malonic acid half thioester. After transforming the resulting β-ketothioester into an appropriate form, the carboxylic acid functionality was regenerated for the next elongation step.

  证明了合成聚酮化合物的迭代方法，其中羧酸的链延长是通过与丙二酸半硫酯的脱羧脱水缩合而进行的。将所得的β-酮硫酯转化为合适的形式后，可将羧酸官能团再生，用于下一步的延伸步骤。
• IZAWA T.; MUKAIYAMA T., CHEM. LETT., 1975, NO 2, 161-164
  作者：IZAWA T.、 MUKAIYAMA T.

  DOI：——

  日期：——
• 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.