2-(N-tert-butyl-N-hydroxylamino)benzothiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(N-tert-butyl-N-hydroxylamino)benzothiazole
• 英文别名: N-(1,3-benzothiazol-2-yl)-N-tert-butylhydroxylamine
• 化学式: C₁₁H₁₄N₂OS
• 分子量: 222.311
• InChiKey: FDSPFIVQWVAIOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N-tert-butyl-N-hydroxylamino)benzothiazole 在 lead dioxide 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以85%的产率得到2-(N-aminoxyl-N-tert-butyl)benzothiazole
  参考文献：
  名称：

  Modulating spin delocalization in conjugated nitroxides: 2-(N-aminoxyl-N-tert-butyl)-benzothiazole

  摘要：

  The first controlled synthesis of the title radical, 1, was achieved by oxidation of a hydroxylamine precursor; the radical itself can thus readily be isolated, studied by ESR and UVvis, and compared to results of computational modeling. The benzothiazole ring induces substantial delocalization of the nitroxide spin density (a(NO) = 9.2 G, a(ring N) = 2.7 G, about 10% more than is seen in the benzimidazole nitroxide analog. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.084
• 作为产物：
  描述：

  苯并噻唑 、 亚硝基叔丁烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以25%的产率得到2-(N-tert-butyl-N-hydroxylamino)benzothiazole
  参考文献：
  名称：

  Modulating spin delocalization in conjugated nitroxides: 2-(N-aminoxyl-N-tert-butyl)-benzothiazole

  摘要：

  The first controlled synthesis of the title radical, 1, was achieved by oxidation of a hydroxylamine precursor; the radical itself can thus readily be isolated, studied by ESR and UVvis, and compared to results of computational modeling. The benzothiazole ring induces substantial delocalization of the nitroxide spin density (a(NO) = 9.2 G, a(ring N) = 2.7 G, about 10% more than is seen in the benzimidazole nitroxide analog. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.084

文献信息

• Modulating spin delocalization in conjugated nitroxides: 2-(N-aminoxyl-N-tert-butyl)-benzothiazole
  作者：Patrick Taylor、Prasanna Ghalsasi、Paul Lahti

  DOI：10.1016/j.tetlet.2004.06.084

  日期：2004.8

  The first controlled synthesis of the title radical, 1, was achieved by oxidation of a hydroxylamine precursor; the radical itself can thus readily be isolated, studied by ESR and UVvis, and compared to results of computational modeling. The benzothiazole ring induces substantial delocalization of the nitroxide spin density (a(NO) = 9.2 G, a(ring N) = 2.7 G, about 10% more than is seen in the benzimidazole nitroxide analog. (C) 2004 Elsevier Ltd. All rights reserved.