trans-N,N'-dibenzoylindigo | 72738-57-9

• 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: trans-N,N'-dibenzoylindigo
• 英文别名: N,N'-dibenzoylindigo；1,1'-dibenzoyl-1H,1'H-[2,2']biindolylidene-3,3'-dione；(E)-1,1'-Dibenzoyl-1H,1'H-[2,2']biindolyliden-3,3'-dion；(2E)-1-benzoyl-2-(1-benzoyl-3-oxoindol-2-ylidene)indol-3-one
• CAS: 72738-57-9
• 化学式: C₃₀H₁₈N₂O₄
• 分子量: 470.484
• InChiKey: SBJBMLPMKUJETC-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-N,N'-dibenzoylindigo 在 氧气 作用下， 以 甲苯 为溶剂， 生成 [1-Benzoyl-2-(4-oxo-3,1-benzoxazin-2-yl)indol-3-yl] benzoate
  参考文献：
  名称：

  Photooxidation of N,N'-Diacylindigo Dyes

  摘要：

  Irradiation of N,N'-diacylindigo dyes in the presence of oxygen resulted in an unusual oxygen insertion/acyl transfer reaction. While this process occurred over many weeks at room temperature, at 100 degrees C it was complete in a few hours. In some cases the yield-of photooxidized product was virtually quantitative. The product structures were proved by spectroscopic methods and in one example by X-ray analysis. A series of mechanistic experiments led to the conclusion that at least the oxygen insertion part of the photooxidation process proceeded via a radical mechanism. The evidence included the following observations: (1) When the photooxidation was conducted in toluene, large amounts of benzyl hydroperoxide were produced; (2) the photooxidation could be achieved in the dark with a radical initiator; (3) attempts to generate the photooxidized product using singlet oxygen chemistry failed. The postulated radical mechanism is described.

  DOI：

  10.1021/jo00105a015
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 mixture of gaseous nitrogen oxides 、 溶剂黄146 作用下， 生成 trans-N,N'-dibenzoylindigo
  参考文献：
  名称：

  Posner, Chemische Berichte, 1926, vol. 59, p. 1814

  摘要：

  DOI：

文献信息

• The Thermal<i>Cis</i>-to-<i>trans</i>Isomerization of<i>N</i>,<i>N</i>′-Diacylindigos. Kinetic Pressure, Solvent, and Substituent Effects
  作者：Yoshimi Sueishi、Kazuo Ohtani、Norio Nishimura

  DOI：10.1246/bcsj.58.810

  日期：1985.3

  The kinetics of the thermal cis-to-trans isomerization of N,N′-diacylindigos(DAI) in various solvents and under high pressures has been studied. N,N′-Dibenzoylindigos(DBI) isomerize about 10 times slower than molecules not having a benzene ring in the acyl groups. The values of the activation volumes were about 8.0 cm3 mol−1 for the former and about 3.0 cm3 mol−1 for the latter. It was suggested that the thermal isomerization proceeds via the biradical mechanism. The positive values of the activation volume have been interpreted in terms of the increase in the intrinsic volume upon activation. The differences in the isomerization rates and the activation parameters between DBI and the others have been ascribed to an additional interaction between the two phenyl rings in the acyl groups in the cis-ground state.

  研究人员对 N,N′-二乙酰靛红 (DAI) 在不同溶剂和高压条件下顺反异构的热动力学进行了研究。N,N′-二苯甲酰基茚二酮（DBI）的异构化速度比酰基中没有苯环的分子慢 10 倍左右。前者的活化体积值约为 8.0 cm3 mol-1，后者约为 3.0 cm3 mol-1。研究表明，热异构化作用是通过双环化机理进行的。活化体积的正值被解释为活化时固有体积的增加。DBI 与其他化合物在异构化速率和活化参数上的差异被归因于顺地态酰基中的两个苯基环之间存在额外的相互作用。
• The Selective Preparation of<i>N</i>-Acylindigo
  作者：Yoshimori Omote、Kiyoko Fujiki、Hiroshi Awano、Ikuo Kubota、Takehiko Nishio、Hiromu Aoyama

  DOI：10.1246/bcsj.54.627

  日期：1981.2

  The hitherto unknown N-acylindigo has been selectively prepared by heating the corresponding known N,N′-diacylindigo in aqueous pyridine. The data of N-acetyl, N-benzoyl, N-(p-toluoyl), N-(p-chlorobenzoyl), N-(p-nitrobenzoyl), and N-(3,5-dinitrobenzoyl)indigo are summarized.

  通过在吡啶水溶液中加热相应的已知 N,N′-二乙酰基靛蓝，选择性地制备了迄今未知的 N-酰基靛蓝。本文总结了 N-乙酰基、N-苯甲酰基、N-（对甲苯甲酰基）、N-（对氯苯甲酰基）、N-（对硝基苯甲酰基）和 N-（3,5-二硝基苯甲酰基）靛蓝的数据。
• Modified indigo compounds and methods of dyeing a substrate using a modified indigo compound
  申请人：VF Jeanswear LP

  公开号：US11208559B2

  公开（公告）日：2021-12-28

  The present disclosure provides dye compounds for use in dyeing textiles.

  本公开提供了用于纺织品染色的染料化合物。
• [1,3] Alkyl migration as a third type of N,N'-dialkanoylindigo photochemistry
  作者：Bradley D. Smith、David E. Alonso、Jeffrey T. Bien、John D. Zielinski、Sheridan L. Smith、Kenneth J. Haller

  DOI：10.1021/jo00075a059

  日期：1993.11
• Liquid-crystalline solvents as mechanistic probes. 17. Influence of cholesteric and smectic mesophase order on the isomerization of some N,N'-diacylindigos
  作者：Srinivasan Ganapathy、Richard G. Zimmermann、Richard G. Weiss

  DOI：10.1021/jo00363a024

  日期：1986.6