4,4'-Dichloroindigo | 6275-44-1

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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: 4,4'-Dichloroindigo
• 英文别名: 4,4'-dichloroindigotin；4,4'-dichloro-1H,1'H-[2,2']biindolylidene-3,3'-dione；(E)-4,4'-dichloro-1H,1'H-[2,2']biindolylidene-3,3'-dione；(E)-4,4'-Dichlor-1H,1'H-[2,2']biindolyliden-3,3'-dion；4.4'-Dichlorindigo；(2E)-4-chloro-2-(4-chloro-3-oxo-1H-indol-2-ylidene)-1H-indol-3-one
• CAS: 6275-44-1
• 化学式: C₁₆H₈Cl₂N₂O₂
• 分子量: 331.158
• InChiKey: ARRVPHBRLHNLMH-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,4'-Dichloroindigo 在 sodium hydroxide 、 sodium dithionite 、 重水 、 氧气 作用下， 以 水 为溶剂， 以76%的产率得到2-[1,3-dihydro-3-oxo-2H-(4-D)indol-2-ylidene]-1,2-dihydro-3H-(4-D)-indol-3-one
  参考文献：
  名称：

  SelectivelyC-Deuterated Indigotins

  摘要：

  Selectively C-deuterated indigotins were synthesized from halogenated indigotins la-e as precursors. The described reactions - used already by the ancient purple dyers - allowed the introduction of D-atoms at defined positions of the indigo molecule. The exchange of halogen atoms by D-atoms was induced by UV irradiation of the leuco compounds 2a-c and 3a-c in D2O. The resulting leuco forms Ja-e were oxidized to the deuterated indigotins 5a-c. Some conclusions were drawn as to the kinetics of the reaction. The physical properties of the new compounds were determined.

  DOI：

  10.1002/1522-2675(20001108)83:11<2884::aid-hlca2884>3.0.co;2-c
• 作为产物：
  描述：

  4-氯吲哚 在 recombinant Escherichia coli BL₂₁ cells expressing Pseudomonas sp. LQ₂₆ styrene monooxygenase 作用下， 生成 4,4'-Dichloroindigo
  参考文献：
  名称：

  Styrene monooxygenase from Pseudomonas sp. LQ26 catalyzes the asymmetric epoxidation of both conjugated and unconjugated alkenes

  摘要：

  A novel styrene monooxygenase (SMO) was isolated from Pseudomonas sp. LQ26, a styrene degrader from activated sludge. Sequence alignment demonstrated that it was the most distant member of all SMOs originating from the genus of Pseudomonas. The substrate spectrum of this enzyme extended beyond typical SMO substrates to 1-allylbenzene analogues, previously reported as non-substrates for the SMO from Pseudomonas fluorescens ST. The results demonstrate for the first time the asymmetric epoxidation of both conjugated and unconjugated alkenes catalyzed by SMO and suggest that a much broader substrate spectrum is expected for SMOs. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.08.012

文献信息

• A facile protection–deprotection route for obtaining indigo pigments as thin films and their applications in organic bulk heterojunctions
  作者：Eric Daniel Głowacki、Gundula Voss、Kadir Demirak、Marek Havlicek、Nevsal Sünger、Aysu Ceren Okur、Uwe Monkowius、Jacek Gąsiorowski、Lucia Leonat、Niyazi Serdar Sariciftci

  DOI：10.1039/c3cc42889c

  日期：——

  Indigo and its derivatives are industrially-important dyes known for centuries. The low solubility of these compounds limits their applications and hinders potential synthetic chemistry using indigo as a building-block. Herein we report attachment of the tert-butoxy carbonyl (tBOC) thermolabile protecting group to indigos, allowing their processing into neat thin films as well as mixed films with a semiconducting polymer. Photoinduced charge transfer is observed to and from these pigments and the polymer.

  靛蓝及其衍生物是几个世纪以来众所周知的重要工业染料。这些化合物的低溶解度限制了它们的应用，并阻碍了以靛蓝为基础的潜在合成化学。在此，我们报告了将叔丁氧基羰基（tBOC）热稳定保护基团附着到靛蓝上，从而将其加工成纯净薄膜以及与半导体聚合物混合薄膜的情况。在这些颜料和聚合物之间观察到了光诱导电荷转移。
• Synthesis and Absorption Spectra of the Symmetrical Chloroindingos
  作者：Peter W. Sadler、Reginald L. Warren

  DOI：10.1021/ja01587a047

  日期：1956.3
• Holt; Sadler, Proceedings of the Royal Society of London. Series B, Biological sciences, 1958, vol. 148, p. 481,488
  作者：Holt、Sadler

  DOI：——

  日期：——