3-cyclohexyl-3-ethynyl-2-methylene-tetrahydrofuran | 1261299-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 3-cyclohexyl-3-ethynyl-2-methylene-tetrahydrofuran
• 英文别名: 3-Cyclohexyl-3-ethynyl-2-methylideneoxolane；3-cyclohexyl-3-ethynyl-2-methylideneoxolane
• CAS: 1261299-66-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: SLKFBURMTGFIFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-allyl-3-cyclohexyl-pentane-2,4-dione 在 potassium osmate(VI) dihydrate 、 sodium tetrahydroborate 、 正丁基锂 、 三苯基膦氯金 、 silver tetrafluoroborate 、 N-甲基吗啉氧化物 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 31.25h， 生成 3-cyclohexyl-3-ethynyl-2-methylene-tetrahydrofuran
  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

文献信息

• Reversal of Selectivity in Gold-Catalyzed Cyclizations of 3,3-Disubstituted 1,4-Diynes
  作者：Roman Rüttinger、Juliane Leutzow、Michael Wilsdorf、Kristina Wilckens、Constantin Czekelius

  DOI：10.1021/ol102628x

  日期：2011.1.21

  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.