3-ethynyl-3-(3-methoxyphenyl)-2-methylene-tetrahydrofuran | 1261299-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethynyl-3-(3-methoxyphenyl)-2-methylene-tetrahydrofuran
• 英文别名: 3-Ethynyl-3-(3-methoxyphenyl)-2-methylideneoxolane；3-ethynyl-3-(3-methoxyphenyl)-2-methylideneoxolane
• CAS: 1261299-71-1
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: RKSYYECLYXZDEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-ethynyl-3-(3-methoxyphenyl)pent-4-ynal 在 sodium tetrahydroborate 、 三苯基膦氯金 、 silver tetrafluoroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.25h， 生成 3-ethynyl-3-(3-methoxyphenyl)-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.