5-anilino-3-ethoxy<2,1>benzisoxazole-4,7-quinone | 101130-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-anilino-3-ethoxy<2,1>benzisoxazole-4,7-quinone
• 英文别名: 5-Anilino-3-ethoxy-2,1-benzoxazole-4,7-dione
• CAS: 101130-40-9
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: NVXKHWOZUQVLFH-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C (decomp)
• 沸点：
  517.9±50.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-anilino-3-ethoxy<2,1>benzisoxazole-4,7-quinone 以 氯苯 为溶剂， 反应 0.7h， 以80%的产率得到(Z)-β-Anilino-γ-cyanocarboethoxymethylidene-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：

  二羟基苯甲酸乙酯 在 lead(IV) acetate 、 sodium periodate 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 20.5h， 生成 5-anilino-3-ethoxy<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

• 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。
• Torres, Tomas; Eswaran, S.V.; Schaefer, Wolfram, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 697 - 699
  作者：Torres, Tomas、Eswaran, S.V.、Schaefer, Wolfram

  DOI：——

  日期：——
• A facile synthesis of alkylidenebutenolides via thermal rearrangement of benzisoxazolequinones
  作者：Tomás Torres、Wolfram Schäfer

  DOI：10.1016/s0040-4039(00)93566-4

  日期：1991.10

  Benzisoxazolequinones 1 readily accesible from 2-carboxy-1,4-hydroquinone undergo thermic induced highly stereoselective rearrangement in solution to produce quantitatively gamma-cyanomethylidenebutenolides 2.
• TORRES, T.;ESWARAN, S. V.;SCHAEFER, W., J. HETEROCYCL. CHEM., 1985, 22, N 3, 697-699
  作者：TORRES, T.、ESWARAN, S. V.、SCHAEFER, W.

  DOI：——

  日期：——
• Stereoselective synthesis of functionalized butenolides by the photochemical rearrangement of [2,1]benzisoxazolequinone derivatives
  作者：Diego Armesto、Salomé Rodríguez-Morgade、María J. Ortiz、Purificación Vázquez、Tomás Torres

  DOI：10.1016/s0040-4020(97)00058-6

  日期：1997.3

  On direct irradiation 3-alkoxy[2,1]benzisoxazolequinones 1a, 1b, 1c, 1e and 3-N-N-dimethylamino[2,1]benzisoxazolequinone1d undergo rearrangement to the corresponding γ-cyano alkylidenebutenolides 3 in high yield. The reaction is highly stereoselective for compounds 1a, 1b, 1c, and 1d yielding the corresponding Z-butenolides 3 as the only stereoisomer. A mechanism involving triplet nitrene intermediates

  在直接辐射下，3-烷氧基[2，1]苯并恶唑啉酮1a，1b，1c，1e和3- N - N-二甲基氨基[2，1]苯并恶唑啉醌1d以高收率重排成相应的γ-氰基亚烷基丁烯内酯3。该反应对于化合物1a，1b，1c和1d具有高度立体选择性，产生相应的Z-丁烯内酯3作为唯一的立体异构体。提出了涉及三线态氮烯中间体的反应机理。