6-nitro-3-phenyl-1,2-benzisoxazole | 934548-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 6-nitro-3-phenyl-1,2-benzisoxazole
• 英文别名: 6-nitro-3-phenyl-benz[d]isoxazole；6-Nitro-3-phenyl-benz[d]isoxazol；6-Nitro-3-phenyl-1,2-benzoxazole
• CAS: 934548-53-5
• 化学式: C₁₃H₈N₂O₃
• 分子量: 240.218
• InChiKey: OYDZCBVBFLOLPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-nitro-3-phenyl-1,2-benzisoxazole 在 copper acetylacetonate sodium tetrahydroborate 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 异丙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 5-oxo-5-[(3-phenyl-1,2-benzisoxazol-6-yl)amino]pentanoic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Catalysis of 3-Carboxy-1,2-benzisoxazole Decarboxylation by Hydrophobic Antibody Binding Pockets

  摘要：

  Monoclonal antibodies were generated against a 3-phenyl-1,2-benzisoxazole derivative and shown to catalyze the solvent-sensitive decarboxylation of 3-carboxy-1,2-benzisoxazoles. In addition to rare accelerations up to 2300-fold over background, the antibodies exhibit distinctive selectivities for substrates bearing 5- or 6-NO2 substituents, with preferential decarboxylation of the less reactive substrate in one case. These effects are the likely consequence of substrate destabilization, achieved by forcing the carboxylate group into a relatively apolar binding pocket and stabilization of the charge-delocalized transition state through dispersive interactions. Comparison with a more active antibody decarboxylase previously raised against 2-acetamido-naphthalene-1,5-disulfonate suggests, however, that a judicious mix of polar and apolar interactions may ultimately be more effective for achieving high decarboxylase activity.

  DOI：

  10.1002/1522-2675(20000906)83:9<2183::aid-hlca2183>3.0.co;2-c
• 作为产物：
  描述：

  2-iodo-4-nitro-benzophenone 在 sodium hydroxide 、 盐酸羟胺 作用下， 生成 6-nitro-3-phenyl-1,2-benzisoxazole
  参考文献：
  名称：

  Willgerodt; Gartner, Chemische Berichte, 1908, vol. 41, p. 2819

  摘要：

  DOI：

文献信息

• Rhodium(<scp>iii</scp>)-catalysed redox neutral alkylation of 3-arylbenzo[<i>d</i>]isoxazoles: easy access to substituted succinimides
  作者：Xuelin Yue、Xiang Zhao、Junwei Huang、Yijie Gao、Yadong Feng、Xiuling Cui

  DOI：10.1039/d3ob00851g

  日期：——

  A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under redox-neutral conditions has been developed, giving a series of substituted succinimides in up to 99% yield. This transformation is highly selective to give succinimides, and Heck-type products are successfully avoided. This protocol features 100% atom-economy and broad substrate tolerance, and provides a novel

  开发了一种在氧化还原中性条件下用马来酰亚胺对3-芳基苯并[ d ]异恶唑进行烷基化的简便方法，得到一系列取代的琥珀酰亚胺，产率高达 99%。这种转化对于得到琥珀酰亚胺具有高度选择性，并且成功地避免了 Heck 型产物。该方案具有100%原子经济性和广泛的底物耐受性，为合成多种琥珀酰亚胺提供了一种新策略，为蛋白质药物的琥珀酰化和药理学家发现一流药物提供了机会。