2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan | 109976-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan
• 英文别名: 3-[2-(1,3-Dioxanyl)]-1-(2-furyl)-1-propanol；3-(1,3-dioxan-2-yl)-1-(furan-2-yl)propan-1-ol
• CAS: 109976-35-4
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: BFRDDOLNTCRBPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan 在 盐酸 、 sodium hydride 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 61.5h， 生成 ethyl 2-fluoro-5-(hydroxy-5-oxo-1-cyclopenten-1-yl)-2-(E)-pentenoate
  参考文献：
  名称：

  Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost

  摘要：

  A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.

  DOI：

  10.1021/jm00394a004
• 作为产物：
  描述：

  糠醛 、 2-(2-溴乙基)-1,3-二氧杂环己烷 在 碘 、 magnesium 、 mercury dichloride 作用下， 生成 2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan
  参考文献：
  名称：

  Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost

  摘要：

  A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.

  DOI：

  10.1021/jm00394a004

文献信息

• Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost
  作者：Paul W. Collins、Steven W. Kramer、Gary W. Gullikson

  DOI：10.1021/jm00394a004

  日期：1987.11

  A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.