2-hydroxy-5-(2-furyl)tetrahydrofuran | 38299-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-hydroxy-5-(2-furyl)tetrahydrofuran
• 英文别名: 5-(Furan-2-yl)oxolan-2-ol
• CAS: 38299-92-2
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: NYWBRBBXSMROAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(2-furyl)tetrahydrofuran 在 吡啶 、 咪唑 、 1-pentynyl copper 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium hydride 、 lithium cyclohexylisopropylamide 、 溶剂黄146 、 sodium iodide 、 zinc(II) chloride 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 41.75h， 生成 methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate
  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：

  2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 28.0h， 以30%的产率得到2-hydroxy-5-(2-furyl)tetrahydrofuran
  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

• Lactols in an asymmetric aldol-desymmetrization sequence: access to tetrahydro-4H-furo[2,3-b]pyran-2-one and tetrahydro-4H-furo[2,3-b]furan-2-one derivatives
  作者：Ji-Yao Li、Ke-Wei Yu、Chao-Chao Xie、Yan-Kai Liu

  DOI：10.1039/c6ob02420c

  日期：——

  An asymmetric aldol-desymmetrization sequence was developed which provided highly efficient access to important bicyclic oxygen-containing scaffolds with multiple chiral centers and one is a quaternary stereogenic center containing a free hydroxy group. Moreover, starting from racemic precursors, the final products were obtained as two separable diastereomers by flash chromatography. Several other

  开发了不对称的醛醇脱对称序列，其提供了对具有多个手性中心的重要的双环含氧支架的高效访问，一个是具有游离羟基的季立体构型中心。此外，从外消旋前体开始，通过快速色谱法将最终产物制成两种可分离的非对映异构体。使用该策略还可以轻松生成其他几个杂环。
• Selvamurugan; Aidhen, Journal of Chemical Research - Part S, 2000, # 12, p. 590 - 592
  作者：Selvamurugan、Aidhen

  DOI：——

  日期：——