N-hydroxyisatin | 6971-68-2

• 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: N-hydroxyisatin
• 英文别名: 1-Hydroxy-isatin；1-Hydroxy-1h-indole-2,3-dione；1-hydroxyindole-2,3-dione
• CAS: 6971-68-2
• 化学式: C₈H₅NO₃
• 分子量: 163.133
• InChiKey: ISRAAHLLSDMDOI-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  370.3±25.0 °C(Predicted)
• 密度：
  1.638±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxyisatin 在 硫酸 作用下， 生成 2,1-苯并异恶唑-3-羧酸
  参考文献：
  名称：

  Alessandri, Gazzetta Chimica Italiana, 1927, vol. 57, p. 209

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯甲酸 在 甲酸 、 氯化亚砜 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 3.08h， 生成 N-hydroxyisatin
  参考文献：
  名称：

  Photochemistry of 2-(methoxycarbonyl)phenyl azide studied by matrix-isolation spectroscopy. A new slippery energy surface for phenylnitrene

  摘要：

  Broad-band irradiation (lambda > 350 nm) of 2-(methoxycarbonyl)phenyl azide (1) in Ar at 10 K monitored by IR and UV-vis spectroscopy resulted in the formation of at least rive major products, all of which were shown to be photointerconvertible under these conditions. The two products showing intact methoxycarbonyl carbonyl stretching absorption bands were assigned as (2-(methoxycarbonyl)phenyl)nitrene (2) and 3-(methoxycarbonyl)-1,2,4,6-azacycloheptatetraene (3), probably formed as a result of ring expansion of 2, while the products showing sharp absorption bands at 2118 and 2088 cm-1 due to ketene functional groups were assigned to the geometrical mixture of carbonyl oximino benzenes 16, presumably formed by formal 1,4-methoxy migration in 2, and the one showing carbonyl absorption at 1857 cm-1 was assigned as N-methoxyazetinone 15, produced as a result of photocyclization of 16. These assignments were unequivocally verified by generating the same reaction mixtures by photodecarbonylation of N-methoxyisatin (23) in an argon matrix at 10 K. That phenylnitrene-pyridylmethylene interconversions were not attained once the 2-methoxycarbonyl group was introduced was also shown.

  DOI：

  10.1021/ja00072a015

文献信息

• Alessandri, Gazzetta Chimica Italiana, 1928, vol. 58, p. 553
  作者：Alessandri

  DOI：——

  日期：——
• Arndt; Partale, Chemische Berichte, 1927, vol. 60, p. 451
  作者：Arndt、Partale

  DOI：——

  日期：——
• Arndt; Eistert; Partale, Chemische Berichte, 1928, vol. 61, p. 1112
  作者：Arndt、Eistert、Partale

  DOI：——

  日期：——
• Reissert, Chemische Berichte, 1908, vol. 41, p. 3925
  作者：Reissert

  DOI：——

  日期：——
• Arndt; Amende; Ender, Monatshefte fur Chemie, 1932, vol. 59, p. 213
  作者：Arndt、Amende、Ender

  DOI：——

  日期：——