bis[2-(N-acetylamino)phenyl] diselenide | 831224-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis[2-(N-acetylamino)phenyl] diselenide
• 英文别名: bis(2-acetylaminophenyl)diselenide；bis-(2-acetylamino-phenyl)-diselenide；Bis-(2-acetylamino-phenyl)-diselenid；Bis-(2-acetamino-phenyl)-diselenid；o-ACETOTOLUIDIDE, alpha, alpha'-DISELENOBIS-；N-[2-[(2-acetamidophenyl)diselanyl]phenyl]acetamide
• CAS: 831224-76-1
• 化学式: C₁₆H₁₆N₂O₂Se₂
• 分子量: 426.235
• InChiKey: CNBPFTNNGNVODJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Et₄N)(Mo(V)O(SePh)4] 、 bis[2-(N-acetylamino)phenyl] diselenide 在 tetraethylammonium borohydride 作用下， 以 乙二醇二甲醚 为溶剂， 以10%的产率得到(NEt4)2[Mo(IV)O(Se-2-CH3CONHC6H4)4]*1.5H2O
  参考文献：
  名称：

  具有分子内NH ... Se氢键的钼（IV）芳硒酸酯的晶体结构和77Se NMR光谱。

  摘要：

  具有分子内NH ... Se氢键，[Mo（IV）O（Se-2-RCONHC6H4）4] 2-（R = t-Bu，CH3，CF3）和[合成了Mo（V）O（Se-2-t-BuCONHC6H4）4]-，并通过1H核磁共振（NMR），77Se NMR，电子自旋共振（ESR），紫外可见光谱，X射线分析对其进行了表征和电化学测量。77Se-1H相关光谱法（COSY）通过1J（77Se-1H）= 5.4 Hz偶合的NH ... Se氢键显示酰胺1H与硒化77Se原子之间的显着相关性。氢键有助于Mo（V）/ Mo（IV）氧化还原电势的正向移动。在（PPh4）2 [Mo（IV）O（Se-2-CH3CONHC6H4）4]的晶体结构中，发现NH ... O = Mo氢键。从头算计算支持分子内NH ... O = Mo和NH ... Se氢键的存在。

  DOI：

  10.1021/ic061140y
• 作为产物：
  描述：

  2-碘乙酰苯胺 在 丁二酰亚胺 、 selenium 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 、 水 、 sodium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以60%的产率得到bis[2-(N-acetylamino)phenyl] diselenide
  参考文献：
  名称：

  Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

  摘要：

  Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.141

文献信息

• Keimatsu; Satoda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1936, vol. 56, p. 600,605
  作者：Keimatsu、Satoda

  DOI：——

  日期：——
• Ochiai; Haginiwa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1947, vol. 67, p. 138
  作者：Ochiai、Haginiwa

  DOI：——

  日期：——
• Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones
  作者：Shah Jaimin Balkrishna、Bhagat Singh Bhakuni、Sangit Kumar

  DOI：10.1016/j.tet.2011.09.141

  日期：2011.12

  Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.
• Crystal Structures and ⁷⁷Se NMR Spectra of Molybdenum(IV) Areneselenolates Having Intramolecular NH···Se Hydrogen Bonds
  作者：Taka-aki Okamura、Kaku Taniuchi、Keonil Lee、Hitoshi Yamamoto、Norikazu Ueyama、Akira Nakamura

  DOI：10.1021/ic061140y

  日期：2006.11.1

  monooxomolybdenum(IV,V) areneselenolates having intramolecular NH...Se hydrogen bonds, [Mo(IV)O(Se-2-RCONHC6H4)4]2- (R = t-Bu, CH3, CF3) and [Mo(V)O(Se-2-t-BuCONHC6H4)4]-, were synthesized and characterized by 1H nuclear magnetic resonance (NMR), 77Se NMR, electron spin resonance (ESR), UV-visible spectra, X-ray analysis, and electrochemical measurements. 77Se-1H correlated spectroscopy (COSY) indicated

  具有分子内NH ... Se氢键，[Mo（IV）O（Se-2-RCONHC6H4）4] 2-（R = t-Bu，CH3，CF3）和[合成了Mo（V）O（Se-2-t-BuCONHC6H4）4]-，并通过1H核磁共振（NMR），77Se NMR，电子自旋共振（ESR），紫外可见光谱，X射线分析对其进行了表征和电化学测量。77Se-1H相关光谱法（COSY）通过1J（77Se-1H）= 5.4 Hz偶合的NH ... Se氢键显示酰胺1H与硒化77Se原子之间的显着相关性。氢键有助于Mo（V）/ Mo（IV）氧化还原电势的正向移动。在（PPh4）2 [Mo（IV）O（Se-2-CH3CONHC6H4）4]的晶体结构中，发现NH ... O = Mo氢键。从头算计算支持分子内NH ... O = Mo和NH ... Se氢键的存在。