6-amino-3-phenyl-1,2-benzisoxazole | 313951-42-7

• 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-amino-3-phenyl-1,2-benzisoxazole
• 英文别名: 3-Phenylbenzo[d]isoxazol-6-amine；3-phenyl-1,2-benzoxazol-6-amine
• CAS: 313951-42-7
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: ACDJSKKLCFFNIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-3-phenyl-1,2-benzisoxazole 以 氯仿 、 N,N-二甲基甲酰胺 、 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：

  6-nitro-3-phenyl-1,2-benzisoxazole 在 copper acetylacetonate sodium tetrahydroborate 作用下， 以 乙醇 、 异丙醇 为溶剂， 以89%的产率得到6-amino-3-phenyl-1,2-benzisoxazole
  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

文献信息

• Catalysis of 3-Carboxy-1,2-benzisoxazole Decarboxylation by Hydrophobic Antibody Binding Pockets
  作者：Kinya Hotta、Kazuya Kikuchi、Donald Hilvert

  DOI：10.1002/1522-2675(20000906)83:9<2183::aid-hlca2183>3.0.co;2-c

  日期：2000.9.6

  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.