ethyl 2-(1-naphthyl)-2-(phthalimide-N-oxy)ethanoate | 1415033-72-5

• 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: ethyl 2-(1-naphthyl)-2-(phthalimide-N-oxy)ethanoate
• 英文别名: Ethyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-naphthalen-1-ylacetate；ethyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-naphthalen-1-ylacetate
• CAS: 1415033-72-5
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: QPIMJNBXFOGQMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alpha-萘乙酸乙酯 、 N-羟基邻苯二甲酰亚胺 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.67h， 以50%的产率得到ethyl 2-(1-naphthyl)-2-(phthalimide-N-oxy)ethanoate
  参考文献：
  名称：

  Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system

  摘要：

  A method was developed for the cross-dehydrogenative coupling of alkylarenes and related compounds with N-hydroxyphthalimide (NHPI) using cerium(IV) ammonium nitrate (CAN) to prepare O-substituted NHPI derivatives. The characteristic feature of the reaction is that NHPI plays a dual role. Thus, in the presence of CAN, NHPI generates the phthalimide-N-oxyl (PINO) radical, which abstracts a hydrogen atom from the benzyl position to form a C-centered radical. The target oxidative cross-coupling product is formed mainly through the recombination of PINO with the C-centered radical. Therefore, NHPI serves as a mediator for the radical process and a reagent for the radical cross-coupling. The target products were obtained in yields from 35 to 80%. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.018

文献信息

• Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system
  作者：Alexander O. Terent'ev、Igor B. Krylov、Mikhail Y. Sharipov、Zoya M. Kazanskaya、Gennady I. Nikishin

  DOI：10.1016/j.tet.2012.10.018

  日期：2012.12

  A method was developed for the cross-dehydrogenative coupling of alkylarenes and related compounds with N-hydroxyphthalimide (NHPI) using cerium(IV) ammonium nitrate (CAN) to prepare O-substituted NHPI derivatives. The characteristic feature of the reaction is that NHPI plays a dual role. Thus, in the presence of CAN, NHPI generates the phthalimide-N-oxyl (PINO) radical, which abstracts a hydrogen atom from the benzyl position to form a C-centered radical. The target oxidative cross-coupling product is formed mainly through the recombination of PINO with the C-centered radical. Therefore, NHPI serves as a mediator for the radical process and a reagent for the radical cross-coupling. The target products were obtained in yields from 35 to 80%. (c) 2012 Elsevier Ltd. All rights reserved.