1-Cyclohex-2-en-1-ylhept-2-yn-1-ol | 1007130-94-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-Cyclohex-2-en-1-ylhept-2-yn-1-ol
• CAS: 1007130-94-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: RPZVEBZEWUUYIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (hexyn-1-yl)silver 、 1-氧杂螺[2.5]辛-4-烯 在 二氯二茂锆 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以53%的产率得到1-Cyclohex-2-en-1-ylhept-2-yn-1-ol
  参考文献：
  名称：

  Zirconium-Promoted Epoxide Rearrangement−Alkynylation Sequence

  摘要：

  [GRAPHICS]Additions of terminal alkynes to electrophiles are important transformations in organic chemistry. Generally, activated terminal alkynes react with epoxides in an S(N)2 fashion to form homopropargylic alcohols. We have developed a new synthetic method to form propargylic alcohols from epoxides and terminal alkynes via 1,2-shifts. This method involves cationic zirconium acetylides as both the activator of epoxides and nucleophiles. line to the mild conditions to pre-activate alkynes with silver nitrate, this synthetic method is useful for both electron-rich and electron-deficient alkynes with other acid- and base-sensitive functional groups.

  DOI：

  10.1021/jo702306k

文献信息

• Zirconium-Promoted Epoxide Rearrangement−Alkynylation Sequence
  作者：Brian J. Albert、Kazunori Koide

  DOI：10.1021/jo702306k

  日期：2008.2.1

  [GRAPHICS]Additions of terminal alkynes to electrophiles are important transformations in organic chemistry. Generally, activated terminal alkynes react with epoxides in an S(N)2 fashion to form homopropargylic alcohols. We have developed a new synthetic method to form propargylic alcohols from epoxides and terminal alkynes via 1,2-shifts. This method involves cationic zirconium acetylides as both the activator of epoxides and nucleophiles. line to the mild conditions to pre-activate alkynes with silver nitrate, this synthetic method is useful for both electron-rich and electron-deficient alkynes with other acid- and base-sensitive functional groups.