4-hydroxy-5-hydroxymethyl-3-methylenetetrahydropyran-2-one | 859427-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-5-hydroxymethyl-3-methylenetetrahydropyran-2-one
• 英文别名: 4-Hydroxy-5-(hydroxymethyl)-3-methylideneoxan-2-one
• CAS: 859427-83-1
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: WVGQWJRUDISHEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-hydroxymethyl-3-methylenetetrahydropyran-2-one 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 四丁基氟化铵 、 silver(I) acetate 、 丙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 266.0h， 生成 3-[5-(4-Chloro-benzyl)-2-oxo-2H-pyran-3-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of arylidene-substituted gelastatin analogues and their screening for MMP-2 inhibitory activity

  摘要：

  A series of arylidene-substituted gelastatin analogues were synthesized in a divergent manner. Each analogue was obtained as a mixture of isomers. Calculation methods were devised to deduce the MMP-2 inhibitory activity of each isomer from the activity of an isomeric mixture and its composition. This protocol is suitable for rapidly generating a variety of arylidene-substituted gelastatin analogues and screening them for highly active inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.037
• 作为产物：
  描述：

  2-{hydroxy-[2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methyl}acrylic acid methyl ester 在 硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到4-hydroxy-5-hydroxymethyl-3-methylenetetrahydropyran-2-one
  参考文献：
  名称：

  Synthesis of arylidene-substituted gelastatin analogues and their screening for MMP-2 inhibitory activity

  摘要：

  A series of arylidene-substituted gelastatin analogues were synthesized in a divergent manner. Each analogue was obtained as a mixture of isomers. Calculation methods were devised to deduce the MMP-2 inhibitory activity of each isomer from the activity of an isomeric mixture and its composition. This protocol is suitable for rapidly generating a variety of arylidene-substituted gelastatin analogues and screening them for highly active inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.037