N-(9H-fluorene-9-yloxy)phthalimide | 204206-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9H-fluorene-9-yloxy)phthalimide
• 英文别名: N-(9H-fluoren-9-yloxy)phthalimide；2-(9H-fluoren-9-yloxy)isoindole-1,3-dione
• CAS: 204206-23-5
• 化学式: C₂₁H₁₃NO₃
• 分子量: 327.339
• InChiKey: DADNACBUQLVQNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(9H-fluorene-9-yloxy)phthalimide 在 sodium acetate 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Catalytic Ortho-Acetoxylation of Masked Benzyl Alcohols via an Exo-Directing Mode

  摘要：

  A Pd-catalyzed ortho-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient exo-type directing group for arene (sp(2)) CH functionalization. Two strategies were demonstrated to remove the directing group through N-O and C-O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method.

  DOI：

  10.1021/acs.orglett.5b01098
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 芴 在 [(IPr)CuCl] 、 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以72%的产率得到N-(9H-fluorene-9-yloxy)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

• Saczewski, Jaroslaw; Hudson, Alan L.; Rybczynska, Apolonia, Acta poloniae pharmaceutica, 2009, vol. 66, # 6, p. 671 - 680
  作者：Saczewski, Jaroslaw、Hudson, Alan L.、Rybczynska, Apolonia

  DOI：——

  日期：——
• 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.
• Catalytic <i>Ortho</i>-Acetoxylation of Masked Benzyl Alcohols via an <i>Exo</i>-Directing Mode
  作者：Zhi Ren、Jonathan E. Schulz、Guangbin Dong

  DOI：10.1021/acs.orglett.5b01098

  日期：2015.6.5

  A Pd-catalyzed ortho-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient exo-type directing group for arene (sp(2)) CH functionalization. Two strategies were demonstrated to remove the directing group through N-O and C-O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method.
• 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.