1-(2-Hydroxy-pentyl)-cyclopropanol | 847199-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-Hydroxy-pentyl)-cyclopropanol
• 英文别名: 1-(2-Hydroxypentyl)cyclopropan-1-ol
• CAS: 847199-72-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: AWGNSIRUEQQWMH-UHFFFAOYSA-N

物化性质

• 沸点：
  251.3±8.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-Hydroxy-pentyl)-cyclopropanol 在 aluminium(III) triflate 、 四氯化钛 、 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,7R)-7-Isopropyl-2-propyl-oxepan-4-one
  参考文献：
  名称：

  A Cyclopropane Fragmentation Approach to Heterocycle Assembly:  A Convergent Synthesis of Oxepanes

  摘要：

  A cyclopropanol fragmentation approach to the synthesis of oxepanes has been developed. This convergent strategy condenses cyclopropyl diols with aldehydes to form an acetal, which is subsequently rearranged to furnish a keto-oxepane. The reaction has been developed as a one-pot procedure, utilizing sequential addition of AI(OTf)(3) and TiCl4. Yields range from 50 to 70% for the sequence. A Zimmerman-Traxler transition state disposing substituents in equatorial positions is consistent with the observed formation of strictly cis products.

  DOI：

  10.1021/ol047426t
• 作为产物：
  描述：

  3-羟基己酸乙酯 、 乙基溴化镁 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以51%的产率得到1-(2-Hydroxy-pentyl)-cyclopropanol
  参考文献：
  名称：

  A Cyclopropane Fragmentation Approach to Heterocycle Assembly:  A Convergent Synthesis of Oxepanes

  摘要：

  A cyclopropanol fragmentation approach to the synthesis of oxepanes has been developed. This convergent strategy condenses cyclopropyl diols with aldehydes to form an acetal, which is subsequently rearranged to furnish a keto-oxepane. The reaction has been developed as a one-pot procedure, utilizing sequential addition of AI(OTf)(3) and TiCl4. Yields range from 50 to 70% for the sequence. A Zimmerman-Traxler transition state disposing substituents in equatorial positions is consistent with the observed formation of strictly cis products.

  DOI：

  10.1021/ol047426t