1-[(1S,2S)-2-(6-Methoxy-naphthalen-2-yl)-cyclopropyl]-ethanone | 134198-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(1S,2S)-2-(6-Methoxy-naphthalen-2-yl)-cyclopropyl]-ethanone
• 英文别名: 1-[(1S,2S)-2-(6-methoxynaphthalen-2-yl)cyclopropyl]ethanone
• CAS: 134198-05-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: LXQSBVRWTPCDHH-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (E)-N-methoxy-3-(6-methoxynaphthalen-2-yl)-N-methylprop-2-enamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[(1S,2S)-2-(6-Methoxy-naphthalen-2-yl)-cyclopropyl]-ethanone
  参考文献：
  名称：

  制备环丙基酮，醛和羧酸的新途径。

  摘要：

  α，β-不饱和N-甲氧基-N-甲基酰胺的环丙烷化提供的环丙基酰胺的收率远高于用相应的酮获得的收率。然后通过添加有机金属试剂可以容易地获得所需的酮。还描述了对包括醛和羧酸在内的各种官能团的获取。

  DOI：

  10.1016/s0040-4039(00)79644-4

文献信息

• Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
  作者：Conner M. Farley、You-Yun Zhou、Nishit Banka、Christopher Uyeda

  DOI：10.1021/jacs.8b08296

  日期：2018.10.10

  Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C-1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.