N-(2-cyclohexylideneethoxy)phthalimide | 1034622-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2-cyclohexylideneethoxy)phthalimide
• 英文别名: 2-(2-Cyclohexylideneethoxy)isoindole-1,3-dione
• CAS: 1034622-05-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: BDRCCBYYQNEKTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烯基环己烷 、 N-羟基邻苯二甲酰亚胺 在 碘苯二乙酸 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以70%的产率得到N-(2-cyclohexylideneethoxy)phthalimide
  参考文献：
  名称：

  Cu-Facilitated C−O Bond Formation Using N-Hydroxyphthalimide: Efficient and Selective Functionalization of Benzyl and Allylic C−H Bonds

  摘要：

  A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and Phl(OAc)(2) in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.

  DOI：

  10.1021/ja8031218

文献信息

• Cu-Facilitated C−O Bond Formation Using <i>N</i>-Hydroxyphthalimide: Efficient and Selective Functionalization of Benzyl and Allylic C−H Bonds
  作者：Ji Min Lee、Eun Ju Park、Seung Hwan Cho、Sukbok Chang

  DOI：10.1021/ja8031218

  日期：2008.6.1

  A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and Phl(OAc)(2) in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.