1-cyclopropylbutane-1,4-diol | 147588-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclopropylbutane-1,4-diol
• 英文别名: 1-Cyclopropylbutane-1,4-diol
• CAS: 147588-64-5
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: NKGYVRWIFVRDLA-UHFFFAOYSA-N

物化性质

• 沸点：
  256.5±8.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 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-cyclopropylbutane-1,4-diol 在 dilithium tetrachlorocuprate 、 三甲基溴硅烷 、 magnesium 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 反式-4-十三碳烯-1-醇
  参考文献：
  名称：

  Alkylation of acetylcyclopropane cyclohexylimine by ethylene oxide derivatives as a key step in the synthesis of some insect acetogenin pheromones

  摘要：

  The interaction of Li derivatives of acetylcyclopropane cyclohexylimine with ethylene, propylene, and isoprene oxides leads efficiently to the corresponding gamma-cyclopropylketols. The cyclopropylcarbinol corresponding to the first of them is smoothly converted under the action of the couple Me3SiBr/ZnBr2 to a linear E-C7-homoallyl bromide, which is then used in the stereocontrolled synthesis of tridec-4E-enyl and trideca-4E, 7Z-dienyl acetates - components of the sex pheromones of some Lepidoptera species.

  DOI：

  10.1007/bf00863822
• 作为产物：
  描述：

  1-cyclopropyl-4-hydroxybutan-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 1-cyclopropylbutane-1,4-diol
  参考文献：
  名称：

  Moiseenkov, Alexander M.; Czeskis, Boris A.; Ivanova, Natalya M., Journal of the Chemical Society. Perkin transactions I, 1991, p. 2639 - 2649

  摘要：

  DOI：

文献信息

• Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent
  作者：Thomas K. Hutton、Kenneth W. Muir、David J. Procter

  DOI：10.1021/ol0358399

  日期：2003.12.1

  undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol. [reaction: see text]

  根据反应中使用的醇助溶剂，γ-不饱和酮会经历由碘化sa（II）介导的两个非常不同的立体选择性环化反应。只需将醇助溶剂从甲醇更改为叔丁醇，即可在前所未有的羟醛螺环化和新型环丁醇形成工艺之间进行切换。[反应：看文字]
• Moiseenkov, Alexander M.; Czeskis, Boris A.; Ivanova, Natalya M., Journal of the Chemical Society. Perkin transactions I, 1991, p. 2639 - 2649
  作者：Moiseenkov, Alexander M.、Czeskis, Boris A.、Ivanova, Natalya M.、Nefedov, Oleg M.

  DOI：——

  日期：——
• Alkylation of acetylcyclopropane cyclohexylimine by ethylene oxide derivatives as a key step in the synthesis of some insect acetogenin pheromones
  作者：N. M. Ivanova、B. E. Cheskis、A. M. Moiseenkov、O. M. Nefedov

  DOI：10.1007/bf00863822

  日期：1992.10

  The interaction of Li derivatives of acetylcyclopropane cyclohexylimine with ethylene, propylene, and isoprene oxides leads efficiently to the corresponding gamma-cyclopropylketols. The cyclopropylcarbinol corresponding to the first of them is smoothly converted under the action of the couple Me3SiBr/ZnBr2 to a linear E-C7-homoallyl bromide, which is then used in the stereocontrolled synthesis of tridec-4E-enyl and trideca-4E, 7Z-dienyl acetates - components of the sex pheromones of some Lepidoptera species.