(3-ethynyl-hex-5-en-1-yn-3-yl)cyclohexane | 1261299-46-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (3-ethynyl-hex-5-en-1-yn-3-yl)cyclohexane
• CAS: 1261299-46-0
• 化学式: C₁₄H₁₈
• 分子量: 186.297
• InChiKey: JLSSDTULVVJTGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (3-ethynyl-hex-5-en-1-yn-3-yl)cyclohexane 在 potassium osmate(VI) dihydrate 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以63%的产率得到4-cyclohexyl-4-ethynyl-hex-5-yne-1,2-diol
  参考文献：
  名称：

  Reversal of Selectivity in Gold-Catalyzed Cyclizations of 3,3-Disubstituted 1,4-Diynes

  摘要：

  A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-selectivity in contrast to compounds incorporating an alkoxy substituent in the 3-position. A mechanistic rationale for this reversal of selectivity is provided.

  DOI：

  10.1021/ol102628x
• 作为产物：
  描述：

  3-allyl-3-cyclohexyl-pentane-2,4-dione 在 正丁基锂 、 二异丙胺 、 氯磷酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以53%的产率得到(3-ethynyl-hex-5-en-1-yn-3-yl)cyclohexane
  参考文献：
  名称：

  Reversal of Selectivity in Gold-Catalyzed Cyclizations of 3,3-Disubstituted 1,4-Diynes

  摘要：

  A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-selectivity in contrast to compounds incorporating an alkoxy substituent in the 3-position. A mechanistic rationale for this reversal of selectivity is provided.

  DOI：

  10.1021/ol102628x