((2S,5R)-5-Vinyl-tetrahydro-furan-2-yl)-methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: ((2S,5R)-5-Vinyl-tetrahydro-furan-2-yl)-methanol
• 英文别名: rac-[(2R,5S)-5-ethenyloxolan-2-yl]methanol,cis；[(2S,5R)-5-ethenyloxolan-2-yl]methanol
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: KBCPCIDYIKJEOR-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2S,5R)-5-Vinyl-tetrahydro-furan-2-yl)-methanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到cis-2-bromomethyl-5-vinyloxolane
  参考文献：
  名称：

  Stereoselective Zirconocene-mediated Ring Transformation of 2-Vinylhetero- cycles to Vinylcarbocycles

  摘要：

  Stereoselective ring transformation of 2-vinylheterocycles to vinylcarbocycles was efficiently carried out by the use of a zirconocene equivalent ("Cp2Zr"). The transformation proceeded through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine ring.

  DOI：

  10.3987/com-03-s(p)8
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 咪唑 、 (+)-2-(2-diphenylphosphinophenyl)-4-isopropyl-1,3-oxazoline 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 77.75h， 生成 ((2S,5R)-5-Vinyl-tetrahydro-furan-2-yl)-methanol
  参考文献：
  名称：

  钯(0)催化合成2,5-二取代四氢呋喃

  摘要：

  A stereoselective cyclization of an allylic ester to 2,5-disubstituted tetrahydrofurans catalyzed by palladium(0) is demonstrated. In this cyclization, acetoxy heptenol (6a) having a free hydroxy group prefered trans isomer to cis isomer. By the use of the protected acetoxy heptenol (6b), the cis selectivity was observed. The stereoselectivity was enhanced by the use of DPPIO ligand.

  DOI：

  10.3987/com-00-s(i)11

文献信息

• Synthesis of 2,5-Disubstituted Tetrahydrofurans Catalyzed by Palladium(0)
  作者：Osamu Hara、Kazushige Fujii、Yasumasa Hamada、Youji Sakagami

  DOI：10.3987/com-00-s(i)11

  日期：——

  A stereoselective cyclization of an allylic ester to 2,5-disubstituted tetrahydrofurans catalyzed by palladium(0) is demonstrated. In this cyclization, acetoxy heptenol (6a) having a free hydroxy group prefered trans isomer to cis isomer. By the use of the protected acetoxy heptenol (6b), the cis selectivity was observed. The stereoselectivity was enhanced by the use of DPPIO ligand.
• Stereoselective Zirconocene-mediated Ring Transformation of 2-Vinylhetero- cycles to Vinylcarbocycles
  作者：Yuji Hanzawa、Hiromichi Kiyono、Takeo Taguchi

  DOI：10.3987/com-03-s(p)8

  日期：——

  Stereoselective ring transformation of 2-vinylheterocycles to vinylcarbocycles was efficiently carried out by the use of a zirconocene equivalent ("Cp2Zr"). The transformation proceeded through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine ring.