1,3-dihydro-3-(oxidophenylimino)-2H-indol-2-one | 19714-18-2

• 分子结构分类: 有机化合物
• 英文名称: 1,3-dihydro-3-(oxidophenylimino)-2H-indol-2-one
• 英文别名: (Z)-N-(2-oxoindolin-3-ylidene)aniline oxide；indoline-2,3-dione-3-(N-phenyl oxime )；Indolin-2,3-dion-3-(N-phenyl-oxim)；N-(2-Oxo-3-indolyliden)-anilin-N-oxid
• CAS: 19714-18-2；76369-68-1
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: KNYZWNFXXATYAZ-SSZFMOIBSA-N

物化性质

• 熔点：
  168-170 °C
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 1,3-dihydro-3-(oxidophenylimino)-2H-indol-2-one 反应 0.25h， 以68%的产率得到2',5'-diphenylspiro[3H-indole-3,3'-isoxazolidin]-2(1H)-one
  参考文献：
  名称：

  A regioselective and diastereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition of stable isatin ketonitrone and various dipolarophiles

  摘要：

  The 1,3-dipolar cycloaddition of stable isatin ketonitrone with various dipolarophiles has been conducted under classical, ionic liquid, and solvent-free conditions to give novel spiro[oxindole-isoxazolidine] derivatives with similar diastereoselectivity. In the presence of the ionic liquid 1-butyl-3-methylimidazolium bromide highly diastereoselective and regioselective cyclocondensation products were obtained in good to excellent yields in the absence of any catalyst. The reaction workup was simple and the ionic liquid was easily recovered from the reaction and reused.

  DOI：

  10.1007/s00706-011-0518-2
• 作为产物：
  描述：

  碘苯二乙酸 在 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 1,3-dihydro-3-(oxidophenylimino)-2H-indol-2-one
  参考文献：
  名称：

  Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

  摘要：

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.

  DOI：

  10.1021/acs.joc.6b02774

文献信息

• Alessandri, Gazzetta Chimica Italiana, 1927, vol. 57, p. 209
  作者：Alessandri

  DOI：——

  日期：——
• Callow; Hope, Journal of the Chemical Society, 1929, p. 1193
  作者：Callow、Hope

  DOI：——

  日期：——
• Tacconi, G.; Righetti, P. P.; Desimoni, G., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 4, p. 679 - 684
  作者：Tacconi, G.、Righetti, P. P.、Desimoni, G.

  DOI：——

  日期：——
• Rupe; Stoecklin, Helvetica Chimica Acta, 1924, vol. 7, p. 566
  作者：Rupe、Stoecklin

  DOI：——

  日期：——
• Rupe; Guggenbuehl, Helvetica Chimica Acta, 1925, vol. 8, p. 359
  作者：Rupe、Guggenbuehl

  DOI：——

  日期：——