2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide | 17213-48-8

• 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: 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
• 英文别名: 1,1'-Dioxy-2-2'-diphenyl-3,3'-diindoliden；Bis-(2-phenyl-3H-indol-3-yliden)-N,N'-dioxid；3-(1-oxido-2-phenylindol-3-yl)-2-phenylindol-1-ium 1-oxide
• CAS: 17213-48-8
• 化学式: C₂₈H₁₈N₂O₂
• 分子量: 414.463
• InChiKey: QQGMWLIVPOBTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide 在 苯肼 作用下， 以 氯仿 为溶剂， 生成 1-oxyl-2-phenyl-3-(1-hydroxy-2-phenylindol-3-yl)indole
  参考文献：
  名称：

  Nucleophilic attack on the nitrone tautomeric form of 1-hydroxy-2-phenylindole

  摘要：

  1-Hydroxy-2-phenylindole exists in solution in both hydroxylamine and nitrone tautomeric forms: the latter is able to add organometallic compounds, forming stable indolinic aminoxyls, which were also prepared for comparison by an independent way. The title compound after irradiation with a mercury lamp lead to a spin adduct, whose identification was proved by deuteration of 1-hydroxy-2-phenylindole at different levels. A mechanism similar to that invoked in the photoreaction of phenyl-tert-butylnitrone with nucleophiles has been proposed in order to interpret this behaviour. A macroscale irradiation of 1-hydroxy-2-phenylindole affording several compounds has also been carried out. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00205-1
• 作为产物：
  描述：

  在 三氯乙酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
  参考文献：
  名称：

  Tosi, Giorgio; Battistoni, Paolo; Bruni, Paolo, Gazzetta Chimica Italiana, 1983, vol. 113, # 3/4, p. 153 - 160

  摘要：

  DOI：

文献信息

• Radical intermediates in the peroxidation of indoles
  作者：Paola Astolfi、Lucedio Greci、Corrado Rizzoli、Paolo Sgarabotto、Giancarlo Marrosu

  DOI：10.1039/b102915k

  日期：——

  2-Substituted and 1,2-disubstituted indoles react with m-chloroperbenzoic acid and hydrogen peroxide in the presence of acid or calcium chloride affording 2- and 3-(3-oxoindol-2-yl)indoles; whereas 2,3-disubstituted indoles, reacting with the same oxidants, lead to the formation of products typical of pentaatomic ring opening. The reaction mechanisms are discussed in terms of electron transfer processes based on the redox potentials of the reagents, the Marcus theory and the reaction products distribution. The reactions of 1-hydroxy-2-phenylindole, which yield 2-phenylisatogen (2-phenyl-3-oxo-3H-indole 1-oxide), bisnitrone and 3-(3-oxoindol-2-yl)indole are also explained by an electron transfer mechanism depending on the oxidant and on the conditions of the reaction. The structures of 2- and 3-(3-oxoindol-2-yl)indoles have been elucidated by X-ray analysis.

  2-取代和1,2-二取代吲哚在酸或氯化钙存在下与间氯过苯甲酸和过氧化氢反应，得到2-和3-(3-氧代吲哚-2-基)吲哚；而2,3-二取代吲哚与相同的氧化剂反应，会形成典型的五原子开环产物。基于试剂的氧化还原电位、Marcus 理论和反应产物分布，从电子转移过程的角度讨论了反应机理。还解释了 1-羟基-2-苯基吲哚的反应，产生 2-苯基 isatogen (2-苯基-3-氧代-3H-吲哚 1-氧化物)、双硝酮和 3-(3-氧代吲哚-2-基)吲哚通过取决于氧化剂和反应条件的电子转移机制。 2-和3-(3-氧代吲哚-2-基)吲哚的结构已通过X射线分析阐明。
• 2,2?-Diphenyl-?3,3?-bi-3H-indole-1,1?-dioxide: Competitive demethylation and redox reactions
  作者：Paolo Bruni、Carla Conti、Giorgio Tosi

  DOI：10.1007/bf00808311

  日期：1988.11
• Colonna, Martino; Poloni, Marino, Gazzetta Chimica Italiana, 1983, vol. 113, # 7/8, p. 481 - 484
  作者：Colonna, Martino、Poloni, Marino

  DOI：——

  日期：——
• Berti, Corrado; Greci, Lucedio; Andruzzi, Romano, Journal of the Chemical Society. Perkin transactions I, 1986, p. 607 - 610
  作者：Berti, Corrado、Greci, Lucedio、Andruzzi, Romano、Trazza, Antonio

  DOI：——

  日期：——
• Electron-transfer reactions. Oxidation of Grignard reagents in the presence of an aminoxyl as a radical-trapping agent
  作者：Patricia Carloni、Lucedio Greci、Pierluigi Stipa、Lennart Eberson

  DOI：10.1021/jo00015a029

  日期：1991.7

  The indole bisnitrone 1 (E1/2red = -0.125 V vs NHE in DMF) reacts with a series of Grignard reagents (RMgX) including primary, secondary, and tertiary alkyls and benzyl and phenyl derivatives, which show different E(OX), by single electron transfer to form C-centered radicals corresponding to the Grignard used. The radicals produced in the reaction were trapped by the (arylimino)indolinone nitroxide 5 to form the alkylated hydroxylamines 6. When the reaction is carried out with a ''cyclizing Grignard'' such as 5-hexenylmagnesium bromide, the uncyclized (5-hexen-1-yl) 6g and cyclized (methylcyclopentyl) 6h alkylated hydroxylamines are both isolated. In all cases, the Marcus theory treatment predicts high electron-transfer rate constants.