1-(1-benzyloxy-propa-1,2-dienyl)-3-naphthalen-2-yl-cyclobutanol | 1019842-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-benzyloxy-propa-1,2-dienyl)-3-naphthalen-2-yl-cyclobutanol
• CAS: 1019842-36-4
• 化学式: C₂₄H₂₂O₂
• 分子量: 342.437
• InChiKey: QPRKLEBZLMWVQQ-QUPDYRNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-benzyloxyallene 、 3-萘-2-基环丁烷-1-酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以82%的产率得到1-(1-benzyloxy-propa-1,2-dienyl)-3-naphthalen-2-yl-cyclobutanol
  参考文献：
  名称：

  Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event

  摘要：

  Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a pi-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an alpha-chiral O-tertiary center which has various synthetic applications.

  DOI：

  10.1021/ja7111299