3-(3-(dimethylamino)phenyl)-5-fluoroindolin-2-one | 1042159-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(3-(dimethylamino)phenyl)-5-fluoroindolin-2-one
• 英文别名: 3-(3-(Dimethylamino)phenyl)-5-fluoroindolin-2-one；3-[3-(dimethylamino)phenyl]-5-fluoro-1,3-dihydroindol-2-one
• CAS: 1042159-64-7
• 化学式: C₁₆H₁₅FN₂O
• 分子量: 270.306
• InChiKey: FODWRTXJQCZXMS-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  421.0±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氟吲哚-2-酮 、 3-氯-N,N-二甲基苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以75%的产率得到3-(3-(dimethylamino)phenyl)-5-fluoroindolin-2-one
  参考文献：
  名称：

  Orthogonal Pd- and Cu-Based Catalyst Systems for C- and N-Arylation of Oxindoles

  摘要：

  In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity.

  DOI：

  10.1021/ja803179s

文献信息

• Orthogonal Pd- and Cu-Based Catalyst Systems for C- and N-Arylation of Oxindoles
  作者：Ryan A. Altman、Alan M. Hyde、Xiaohua Huang、Stephen L. Buchwald

  DOI：10.1021/ja803179s

  日期：2008.7.1

  In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity.