1-methyl-2,1-benzisoxazol-3(1H)-one | 90720-10-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-methyl-2,1-benzisoxazol-3(1H)-one
• 英文别名: 1-Methyl-2,1-benzoxazol-3(1H)-one；1-methyl-1H-benzo[c]isoxazol-3-one；1-methyl-1H-benz[c]isoxazol-3-one；1-Methyl-1H-benz[c]isoxazol-3-on；Benzofuran-2-one, 3-methyl-3-aza-2,3-dihydro-；1-methyl-2,1-benzoxazol-3-one
• CAS: 90720-10-8
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: MKFTWUUKJRJMAD-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C(Solv: ligroine (8032-32-4))
• 沸点：
  238.1±23.0 °C(Predicted)
• 密度：
  1.398 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2,1-benzisoxazol-3(1H)-one 600.0 ℃ 、6.67 Pa 条件下， 以75%的产率得到六氢-1,3,5-三苯基-1,3,5-三嗪
  参考文献：
  名称：

  A comparison of some pyrolysis reactions of benzotriazoles, benzisoxazolones and benzisothiazolones

  摘要：

  通过闪蒸真空热解法得到的N-乙酰基、N-甲基、N-苄基以及N-杂芳基取代的苯并三唑、2,1-苯并恶唑-3-酮和2,1-苯并噻唑-3-酮的产物已进行了比较。苯并三唑和苯并异恶唑酮的热解过程似乎涉及亚胺卡宾中间体，尽管N-苄基衍生物通过自由基途径反应。苯并异噻唑酮似乎形成了亚胺炔酮中间体。

  DOI：

  10.1039/b004825i
• 作为产物：
  描述：

  2-(羟基-甲基-氨基)-苯甲酸 在 盐酸 作用下， 生成 1-methyl-2,1-benzisoxazol-3(1H)-one
  参考文献：
  名称：

  Bamberger; Pyman, Chemische Berichte, 1909, vol. 42, p. 2312

  摘要：

  DOI：

文献信息

• Benzisoxazolones: antimicrobial and antileukemic activity
  作者：W. Wierenga、B. R. Evans、G. E. Zurenko

  DOI：10.1021/jm00375a022

  日期：1984.9

  1-(hydroxymethyl)-2,1-benzisoxazol-3(1H)-one which exhibited broad-spectrum antimicrobial and cytotoxic activity. A number of analogues were prepared by employing a modified zinc-reduction procedure on o-nitrobenzoate. Several of these analogues exhibited interesting antipseudomonal activity in agar and broth but were ineffective in vivo.

  不寻常的酸介导的邻硝基苯乙烯氧化物的重排提供了1-（羟甲基）-2,1-苯并恶唑-3（1H）-，它具有广谱抗菌和细胞毒活性。通过在邻硝基苯甲酸酯上采用改进的锌还原程序制备了许多类似物。这些类似物中的几种在琼脂和肉汤中表现出令人感兴趣的抗假单胞菌活性，但在体内无效。
• Heller, Chemische Berichte, 1910, vol. 43, p. 1915
  作者：Heller

  DOI：——

  日期：——
• Photochemistry of 2-(methoxycarbonyl)phenyl azide studied by matrix-isolation spectroscopy. A new slippery energy surface for phenylnitrene
  作者：Hideo Tomioka、Naoki Ichikawa、Kazunori Komatsu

  DOI：10.1021/ja00072a015

  日期：1993.9

  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.
• A comparison of some pyrolysis reactions of benzotriazoles, benzisoxazolones and benzisothiazolones
  作者：Wit K. Janowski、Rolf H. Prager、Jason A. Smith

  DOI：10.1039/b004825i

  日期：——

  The products of flash vacuum pyrolysis of N-acetyl, N-methyl, N-benzyl and N-heteroaryl-substituted benzotriazole, 2,1-benzoxazol-3-one and 2,1-benzothiazol-3-one have been compared. The pyrolysis of benzotriazoles and benzisoxazolones appears to involve an iminocarbene intermediate, although the N-benzyl analogues react by radical pathways. Benzisothiazolones appear to form iminoketene intermediates.

  通过闪蒸真空热解法得到的N-乙酰基、N-甲基、N-苄基以及N-杂芳基取代的苯并三唑、2,1-苯并恶唑-3-酮和2,1-苯并噻唑-3-酮的产物已进行了比较。苯并三唑和苯并异恶唑酮的热解过程似乎涉及亚胺卡宾中间体，尽管N-苄基衍生物通过自由基途径反应。苯并异噻唑酮似乎形成了亚胺炔酮中间体。
• Bamberger; Pyman, Chemische Berichte, 1909, vol. 42, p. 2312
  作者：Bamberger、Pyman

  DOI：——

  日期：——