4-hydroxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one | 55848-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-Hydroxy-6-phenylethyl-5,6-dihydro-2-pyron；4-hydroxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• CAS: 55848-89-0
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UNBTWZJRDJZBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one 、 硫酸二甲酯 以84%的产率得到
  参考文献：
  名称：

  IZAWA T.; MUKAIYAMA T., CHEM. LETT., 1975, NO 2, 161-164

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基-5-苯基戊酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 以366 mg的产率得到4-hydroxy-6-(2-phenylethyl)-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

• HIV PROTEASE INHIBITORS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1112269A2

  公开（公告）日：2001-07-04
• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEASE DU VIH
  申请人：WARNER LAMBERT CO

  公开号：WO2000015634A2

  公开（公告）日：2000-03-23

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.
• 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.
• IZAWA T.; MUKAIYAMA T., CHEM. LETT., 1975, NO 2, 161-164
  作者：IZAWA T.、 MUKAIYAMA T.

  DOI：——

  日期：——