5-Anilino-3-methyl<2,1>benzisoxazole-4,7-quinone | 33229-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Anilino-3-methyl<2,1>benzisoxazole-4,7-quinone
• 英文别名: 5-anilino-3-methyl-benzo[c]isoxazole-4,7-dione；5-Anilino-3-methyl-2,1-benzoxazole-4,7-dione
• CAS: 33229-20-8
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: SURJWHIEROKMMG-UHFFFAOYSA-N

物化性质

• 沸点：
  483.1±45.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Anilino-3-methyl<2,1>benzisoxazole-4,7-quinone 以 various solvent(s) 为溶剂， 反应 5.5h， 以90%的产率得到(Z)-β-Anilino-γ-cyanoacetylmethylidene-Δ^α,β-butenolide
  参考文献：
  名称：

  苯并异恶唑和萘并恶唑醌在溶液和固态中的热重排。立体选择性合成γ-氰基亚甲基丁烯内酯。

  摘要：

  易获得的苯并异恶唑醌1在溶液中经历热诱导的高度立体选择性重排，从而定量提供γ-氰基亚甲基丁烯化物3。该转化可以通过形成乙烯基亚硝基中间体4来解释，该乙烯基中间体经历分子内酸催化的重排。在迈克尔加成反应中，化合物3容易与醇反应。另一方面，苯并异恶唑醌1和萘并恶唑醌2在固态下进行分子间热重排，从而在这种情况下分别给出相应的N-甲基异恶唑酮醌20和11作为主要产物。

  DOI：

  10.1016/s0040-4020(01)80370-7
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 sodium periodate 、 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 20.5h， 生成 5-Anilino-3-methyl<2,1>benzisoxazole-4,7-quinone
  参考文献：
  名称：

  Synthesis and evaluation of a series of 3,5-disubstituted benzisoxazole-4,7-diones. Potent radiosensitizers in vitro

  摘要：

  A series of 3,5-disubstituted-2,1-benzisoxazole-4,7-diones was synthesized and evaluated as radiosensitizers both in vitro and in vivo. These compounds were designed as non-nitro electron-affinic agents in an effort to alleviate some of the toxicities seen with the 2-nitroimidazole radiosensitizers evaluated in the clinic. Several compounds in this series were potent radiosensitizers in vitro, with sensitizer enhancement ratios of 2.0-2.3 at concentrations < 0.5 mM. Compounds with potent in vitro activity were also evaluated in vivo. However, none of these compounds showed radiosensitizing activity in vivo. The reduction potentials of these compounds were determined by cyclic voltammetry and compared to other electron-affinic radiosensitizers. In general, the reduction potentials of this series of compounds was slightly more positive than the 2-nitroimidazoles, but they fell within the range postulated as acceptable to yield in vivo activity. The results suggest that factors other than reduction potential may be responsible for the lack of in vivo radiosensitizing activity observed for this class of radiosensitizers.

  DOI：

  10.1021/jm00115a019

文献信息

• A New Convenient Synthesis of Phosphoranylideneaminoquinones from Isoxazolequinones
  作者：Salomé Rodríguez-Morgade、Tomás Torres、Purificación Vázquez

  DOI：10.1055/s-1993-26033

  日期：——

  The reaction of [2,1]benzisoxazole-4,7-quinones 1 and naphth [2,3-c]isoxazole-4,9-quinone 4 with phosphines leads to phosphoranylideneaminoquinones 2 and 5, respectively, in good to excellent yields.

  [2,1]苯并异噁唑-4,7-醌 1 和萘并[2,3-c]异噁唑-4,9-醌 4 与膦反应，可分别生成磷酰亚氨基醌 2 和 5，产率从良好到极佳。
• Schaefer,W. et al., Angewandte Chemie, 1971, vol. 83, p. 442 - 443
  作者：Schaefer,W. et al.

  DOI：——

  日期：——
• Schaefer,W. et al., Synthesis, 1974, p. 30 - 32
  作者：Schaefer,W. et al.

  DOI：——

  日期：——
• Thermal rearrangement of benzisoxazole- and naphthisoxazolequinones in solution and in the solid state. Stereoselective synthesis of γ-cyanomethylidenebutenolides.
  作者：M.Victoria Martínez-Díaz、Salomé Rodríguez-Morgade、Wolfram Schäfer、Tomás Torres

  DOI：10.1016/s0040-4020(01)80370-7

  日期：1993.3

  accessible benzisoxazolequinones 1 undergo thermal induced highly stereoselective rearrangement in solution to afford quantitatively γ-cyanomethylidenebutenolides 3. The transformation can be explained by the formation of a vinylogous nitrene intermediate 4, which undergoes an intramolecular acid-catalysed rearrangement. Compounds 3 react easily with alcohols in Michael addition. On the other hand,

  易获得的苯并异恶唑醌1在溶液中经历热诱导的高度立体选择性重排，从而定量提供γ-氰基亚甲基丁烯化物3。该转化可以通过形成乙烯基亚硝基中间体4来解释，该乙烯基中间体经历分子内酸催化的重排。在迈克尔加成反应中，化合物3容易与醇反应。另一方面，苯并异恶唑醌1和萘并恶唑醌2在固态下进行分子间热重排，从而在这种情况下分别给出相应的N-甲基异恶唑酮醌20和11作为主要产物。
• Synthesis and evaluation of a series of 3,5-disubstituted benzisoxazole-4,7-diones. Potent radiosensitizers in vitro
  作者：Mark J. Suto、Michael A. Stier、R. Thomas Winters、William R. Turner、Cheryl D. Pinter、William E. Elliott、Judith S. Sebolt-Leopold

  DOI：10.1021/jm00115a019

  日期：1991.11

  A series of 3,5-disubstituted-2,1-benzisoxazole-4,7-diones was synthesized and evaluated as radiosensitizers both in vitro and in vivo. These compounds were designed as non-nitro electron-affinic agents in an effort to alleviate some of the toxicities seen with the 2-nitroimidazole radiosensitizers evaluated in the clinic. Several compounds in this series were potent radiosensitizers in vitro, with sensitizer enhancement ratios of 2.0-2.3 at concentrations < 0.5 mM. Compounds with potent in vitro activity were also evaluated in vivo. However, none of these compounds showed radiosensitizing activity in vivo. The reduction potentials of these compounds were determined by cyclic voltammetry and compared to other electron-affinic radiosensitizers. In general, the reduction potentials of this series of compounds was slightly more positive than the 2-nitroimidazoles, but they fell within the range postulated as acceptable to yield in vivo activity. The results suggest that factors other than reduction potential may be responsible for the lack of in vivo radiosensitizing activity observed for this class of radiosensitizers.