3-phenylimino-2-methyl-1-oxy-2-phenyl-2,3-dihydroindol-5-one | 128792-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-phenylimino-2-methyl-1-oxy-2-phenyl-2,3-dihydroindol-5-one
• 英文别名: 2-Methyl-1-oxido-2-phenyl-3-phenyliminoindol-1-ium-5-one
• CAS: 128792-10-9
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: BDDZJKLXJIYJNM-UHFFFAOYSA-N

物化性质

• 沸点：
  508.2±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenylimino-2-methyl-1-oxy-2-phenyl-2,3-dihydroindol-5-one 在 4 A molecular sieve 、 苯肼 作用下， 以 苯 为溶剂， 以82%的产率得到2-Methyl-2-phenyl-3-[(E)-phenylimino]-2,3-dihydro-1H-indol-5-ol
  参考文献：
  名称：

  Chemical and electrochemical reduction of 2H-indole-3,5-dione and -dione 3-imine N-oxides

  摘要：

  Five of the title N-oxides 1 when reduced either chemically (phenylhydrazine, hydrazobenzene) or electrochemically (DMF-TEAP-protonating agent) were found to afford the corresponding 5-hydroxyindoles 6. The reduction process takes place in two steps leading initially to 1,5-dihydroxyindoles 4 which undergo loss of water and are eventually converted into the products. EPR spectroscopic studies of the chemical and electrochemical reduction led to the characterization of the intermediate radical anions and neutral radicals, and a mechanism based on these results as well as on polarographic and cyclic voltammetric studies is proposed for the process.

  DOI：

  10.1039/p29930002217
• 作为产物：
  描述：

  1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-phenylimino-1-oxyl 、 碘代叔丁烷 在 potassium superoxide 、 18-冠醚-6 作用下， 以 苯 为溶剂， 反应 24.0h， 以12%的产率得到[1-tert-Butoxy-2-methyl-2-phenyl-1,2-dihydro-indol-(3E)-ylidene]-phenyl-amine
  参考文献：
  名称：

  在烷基卤化物存在下，吲哚啉氮氧化物与超氧自由基阴离子的反应。意外形成减少的转置产物

  摘要：

  这项研究涉及2-甲基-2-苯基-3-苯基亚氨基-2,3-二氢吲哚-1-氧基与2,2,6,6-四甲基哌啶-1-氧基与烷基过氧化物的反应，该反应由过氧化钾和α-羟基生成。系列烷基卤，以评估与伯，仲和叔烷基过氧基的反应性可能存在的差异。为了更好地理解所研究的吲哚啉氨基基在碱性介质中的反应性，研究扩展到它与氢氧化钾和叔丁醇钾在不同溶剂中的反应。

  DOI：

  10.1002/jhet.5570400309

文献信息

• Reaction of indolinonic aminoxyls with nitric oxide
  作者：Elisabetta Damiani、Lucedio Greci、Corrado Rizzoli

  DOI：10.1039/b100508l

  日期：——

  unsubstituted N-nitro and N-nitroso stable compounds as the main products, while mono and dinitro compounds are formed in minor yields. In the presence of oxygen, the formation of the corresponding quinone imine N-oxide is observed. Mechanisms for the formation of the reaction products are proposed and discussed, leading to new insights into the chemistry of nitric oxide with aminoxyls. Crystal structures of

  2-甲基-2-苯基-3-氧代吲哚-1-基氧基和2-甲基-2-苯基-3-芳基吲哚-1-基氧基在不存在和存在氧的情况下与一氧化氮反应形成取代和未取代的N -硝基和N-亚硝基稳定的化合物为主要产物，而单和二硝基化合物的生成收率较低。在氧气存在下，观察到相应的醌亚胺N-氧化物的形成。提出和讨论了反应产物的形成机理，从而导致了对一氧化氮的化学反应的新见解。氨基二甲苯。的晶体结构2-甲基-2-苯基-N-亚硝基吲哚-3-一 和 2-甲基-2-苯基-N-硝基吲哚-3-酮 已经确定。
• Cardellini, Liberato; Carloni, Patricia; Greci, Lucedio, Gazzetta Chimica Italiana, 1989, vol. 119, # 12, p. 621 - 626
  作者：Cardellini, Liberato、Carloni, Patricia、Greci, Lucedio、Stipa, Pierluigi、Faucitano, Antonio

  DOI：——

  日期：——
• Reactions of an indolinonic nitroxide with superoxide radical anion in the presence of alkylhalides. Unexpected formation of a reduced transposed product
  作者：Patricia Carloni、Roberto Vianelli、Lucedio Greci

  DOI：10.1002/jhet.5570400309

  日期：2003.5

  study concerns the reactions of 2-methyl-2-phenyl-3-phenylimino-2,3-dihydroindol-l-oxyl and 2,2,6,6-tetramethylpiperidine-1-oxyl with alkylperoxyls, generated from potassium superoxide and a series of alkylhalides, in order to evaluate possible differences in reactivity with primary, secondary and tertiary alkylperoxyls. To better understand the reactivity of the studied indolinonic aminoxyl in alkaline

  这项研究涉及2-甲基-2-苯基-3-苯基亚氨基-2,3-二氢吲哚-1-氧基与2,2,6,6-四甲基哌啶-1-氧基与烷基过氧化物的反应，该反应由过氧化钾和α-羟基生成。系列烷基卤，以评估与伯，仲和叔烷基过氧基的反应性可能存在的差异。为了更好地理解所研究的吲哚啉氨基基在碱性介质中的反应性，研究扩展到它与氢氧化钾和叔丁醇钾在不同溶剂中的反应。
• Chemical and electrochemical reduction of 2H-indole-3,5-dione and -dione 3-imine N-oxides
  作者：Patricia Carloni、Elisabetta Damiani、Lucedio Greci、Pierluigi Stipa、Angelo Albert、Massimo Benaglia、Giancarlo Marrosu、Rita Petrucci、Antonio Trazza

  DOI：10.1039/p29930002217

  日期：——

  Five of the title N-oxides 1 when reduced either chemically (phenylhydrazine, hydrazobenzene) or electrochemically (DMF-TEAP-protonating agent) were found to afford the corresponding 5-hydroxyindoles 6. The reduction process takes place in two steps leading initially to 1,5-dihydroxyindoles 4 which undergo loss of water and are eventually converted into the products. EPR spectroscopic studies of the chemical and electrochemical reduction led to the characterization of the intermediate radical anions and neutral radicals, and a mechanism based on these results as well as on polarographic and cyclic voltammetric studies is proposed for the process.