5-fluoro-3-hydroxy-3-(2-(naphthalen-1-yl)-2-oxoethyl)indolin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-fluoro-3-hydroxy-3-(2-(naphthalen-1-yl)-2-oxoethyl)indolin-2-one
• 英文别名: 5-fluoro-3-hydroxy-3-[2-(naphthalen-1-yl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one；5-fluoro-3-hydroxy-3-(2-naphthalen-1-yl-2-oxoethyl)-1H-indol-2-one
• 化学式: C₂₀H₁₄FNO₃
• 分子量: 335.334
• InChiKey: QKVSBGBEJCTWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-萘乙酮 、 5-氟吲哚-2-酮 在 copper(I) oxide 、 potassium phosphate 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 作用下， 反应 48.0h， 以76%的产率得到5-fluoro-3-hydroxy-3-(2-(naphthalen-1-yl)-2-oxoethyl)indolin-2-one
  参考文献：
  名称：

  CU₂O-Catalyzed C(SP³)-H/C(SP³)-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles

  摘要：

  A simple, convenient, and efficient oxidative cross-coupling reaction of oxindoles with ketones toward a variety of 3-(2-oxoalkyl)-3-hydroxyoxindoles in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative cross-coupling by using 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of oxindoles.

  DOI：

  10.1080/00397911.2015.1111383

文献信息

• C<scp>U</scp>₂O-Catalyzed C(<scp>SP</scp>³)-H/C(<scp>SP</scp>³)-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles
  作者：Baoshuang Wang、Jiayi Zhu、Yang Wei、Guotian Luo、Hongen Qu、Liang-Xian Liu

  DOI：10.1080/00397911.2015.1111383

  日期：2015.12.17

  A simple, convenient, and efficient oxidative cross-coupling reaction of oxindoles with ketones toward a variety of 3-(2-oxoalkyl)-3-hydroxyoxindoles in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative cross-coupling by using 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of oxindoles.