4-benzyl-4-ethynyl-hex-5-yn-1-ol | 1261299-59-5

• 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: 4-benzyl-4-ethynyl-hex-5-yn-1-ol
• 英文别名: 4-Benzyl-4-ethynylhex-5-yn-1-ol；4-benzyl-4-ethynylhex-5-yn-1-ol
• CAS: 1261299-59-5
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: OGCUNHNDGHLAIV-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：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-benzyl-4-ethynyl-hex-5-yn-1-ol 在 三苯基膦氯金 、 silver tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62%的产率得到3-benzyl-3-ethynyl-2-methylene-tetrahydro-2H-pyran
  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-苄基-2,4-戊二酮 在 正丁基锂 、 sodium hydride 、 二异丙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 33.0h， 生成 4-benzyl-4-ethynyl-hex-5-yn-1-ol
  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.