5,6-dibromo-1,1,3,3-tetramethylisoindolin-2-yloxyl | 221368-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5,6-dibromo-1,1,3,3-tetramethylisoindolin-2-yloxyl
• CAS: 221368-79-2
• 化学式: C₁₂H₁₄Br₂NO
• 分子量: 348.057
• InChiKey: XNJATFVOQYRTDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-dibromo-1,1,3,3-tetramethylisoindolin-2-yloxyl 在 四(三苯基膦)钯 N,N-二甲基乙醇胺 、 zinc diacetate 、 氨 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of nitroxide-functionalized phthalocyanines

  摘要：

  A nitroxide-functionalized phthalonitrile and a diimino-isoindoline were prepared via Pd(0)-catalyzed cyanation from the corresponding dibromide and subsequent addition of ammonia, without interference from the radical moieties. The structures of these radicals were confirmed by single-crystal X-ray structure determinations. Metal-templated macrocyclization of these species under standard Linstead conditions or in 2-(dimethylamino)ethanol at reflux gave the corresponding metallated and free-base phthalocyanines, which were characterized using UV-vis, FTIR and EPR spectroscopy as well as mass spectrometry. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.170
• 作为产物：
  描述：

  5,6-二溴-1,1,3,3-四甲基异吲哚啉 在 sodium tungstate 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 120.0h， 生成 5,6-dibromo-1,1,3,3-tetramethylisoindolin-2-yloxyl
  参考文献：
  名称：

  WO2007/124543

  摘要：

  公开号：

文献信息

• Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation
  作者：Daniel J. Keddie、Therese E. Johnson、Dennis P. Arnold、Steven E. Bottle

  DOI：10.1039/b504354a

  日期：——

  class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and

  提出了一种新的结构类型的异吲哚啉氮氧化物（氨氧基）的合成方法，该结构可通过钯催化的Heck反应获得。芳基溴胺，5-溴-1,1,3,3-四甲基异吲哚啉（4）或二溴胺，5,6-二溴-1,1,3,3-四甲基异吲哚啉（5）或类似的溴硝基氧化物6和7的反应用丙烯酸甲酯得到丙烯酸酯取代的四甲基异二氢吲哚胺8和10以及氮氧化物12和14。类似地，芳基溴化物和二溴化物4-7与4-乙烯基苯甲酸甲酯反应得到羧基苯乙烯基取代的四甲基异吲哚啉胺9和11以及类似的氮氧化物13。 15，羧基苯乙烯基四甲基异吲哚啉氮氧化物显示出强烈抑制的荧光，该荧光是通过还原或自由基偶联除去自由基后显示的。
• Micallef, Aaron S.; Bott, Raymond C.; Bottle, Steven E., Journal of the Chemical Society. Perkin transactions II, 1999, # 1, p. 65 - 72
  作者：Micallef, Aaron S.、Bott, Raymond C.、Bottle, Steven E.、Smith, Graham、White, Jonathon M.、et al.

  DOI：——

  日期：——
• Selective transition enhancement in a g‐engineered diradical
  作者：Joe Komeda、Athanassios Boudalis、Nicolas Montenegro-Pohlhammer、Cyril Antheaume、Asato Mizuno、Philippe Turek、Mario Ruben

  DOI：10.1002/chem.202400420

  日期：——

  A diradical with engineered g‐asymmetry was synthesized by grafting a nitroxide radical onto the [Y(Pc)2]˙ radical platform. Various spectroscopic techniques and computational studies revealed that the electronic structures of the two spin systems remained minimally affected within the diradical system. Fluid‐solution Electron Paramagnetic Resonance (EPR) experiments revealed a weak exchange coupling with |J| ~ 0.014 cm‐1, subsequently rationalized by CAS‐SCF calculations. Frozen solution continuous‐wave (CW) EPR experiments showed a complicated and power‐dependent spectrum that eluded analysis using the point‐dipole model. Pulse EPR manipulations with varying microwave powers, or under varying magnetic fields, demonstrated that different resonances could be selectively enhanced or suppressed, based on their different tipping angles. In particular, Field‐Swept Echo‐Detected (FSED) spectra revealed absorptions of MW power‐dependent intensities, while Field‐Swept Spin Nutation (FSSN) experiments revealed two distinct Rabi frequencies. This study introduces a methodology to synthesize and characterize g‐asymmetric two‐spin systems, of interest in the implementation of spin‐based CNOT gates.
• WO2007/124543
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of nitroxide-functionalized phthalocyanines
  作者：Anthony G.M. Barrett、Graeme R. Hanson、Andrew J.P. White、David J. Williams、Aaron S. Micallef

  DOI：10.1016/j.tet.2007.03.170

  日期：2007.6

  A nitroxide-functionalized phthalonitrile and a diimino-isoindoline were prepared via Pd(0)-catalyzed cyanation from the corresponding dibromide and subsequent addition of ammonia, without interference from the radical moieties. The structures of these radicals were confirmed by single-crystal X-ray structure determinations. Metal-templated macrocyclization of these species under standard Linstead conditions or in 2-(dimethylamino)ethanol at reflux gave the corresponding metallated and free-base phthalocyanines, which were characterized using UV-vis, FTIR and EPR spectroscopy as well as mass spectrometry. (c) 2007 Elsevier Ltd. All rights reserved.