3-(5-methylene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester | 859427-91-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(5-methylene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester
• CAS: 859427-91-1
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: NEEIJWVBIOKQRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(5-methylene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester 、 对氯碘苯 在 palladium diacetate 、 silver(I) acetate 、 三苯基膦 、 lithium hydroxide 作用下， 以 乙腈 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 3-[5-(4-Chloro-benzyl)-2-oxo-2H-pyran-3-yl]-propionic acid 、 3-{5-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-2-oxo-5,6-dihydro-2H-pyran-3-yl}-propionic acid 、 3-{5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-oxo-5,6-dihydro-2H-pyran-3-yl}-propionic acid
  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 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 四丁基氟化铵 、 丙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 244.0h， 生成 3-(5-methylene-2-oxo-5,6-dihydro-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