3-tert-butyl 5-methyl 2-oxo-1,3-benzoxazole-3,5(2H)-dicarboxylate | 1159569-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-tert-butyl 5-methyl 2-oxo-1,3-benzoxazole-3,5(2H)-dicarboxylate
• CAS: 1159569-61-5
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: BIFXVRYPTYDWCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-tert-butyl 5-methyl 2-oxo-1,3-benzoxazole-3,5(2H)-dicarboxylate 在 甲醇 、 caesium carbonate 作用下， 反应 12.0h， 以71%的产率得到methyl 3-[(tert-butoxycarbonyl)amino]-4-hydroxybenzoate
  参考文献：
  名称：

  Synthetic Approaches to Amino Analogues of N-Acetylcolchinol

  摘要：

  A straightforward synthesis of aminodibenzoxepines, new analogues of N-acetyleolchinol, is reported by using two different strategies. The first strategy involves a Grignard addition, a biaryl Suzuki-Miyaura coupling, and a HF-mediated cyclodehydration as key steps. A second strategy, better adapted to the synthesis of analogues bearing a benzylic substituent, was designed by inverting the order of the Grignard addition and the biaryl coupling. This allowed the rapid and reliable production of a series of substituted aminodibenzoxepines. A chelate model was proposed to account for the diastereoselectivity observed in the Grignard addition step.

  DOI：

  10.1021/jo900632a
• 作为产物：
  描述：

  2-氧代-2,3-二氢-1,3-苯并噁唑-5-羧酸甲酯 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以95%的产率得到3-tert-butyl 5-methyl 2-oxo-1,3-benzoxazole-3,5(2H)-dicarboxylate
  参考文献：
  名称：

  Synthetic Approaches to Amino Analogues of N-Acetylcolchinol

  摘要：

  A straightforward synthesis of aminodibenzoxepines, new analogues of N-acetyleolchinol, is reported by using two different strategies. The first strategy involves a Grignard addition, a biaryl Suzuki-Miyaura coupling, and a HF-mediated cyclodehydration as key steps. A second strategy, better adapted to the synthesis of analogues bearing a benzylic substituent, was designed by inverting the order of the Grignard addition and the biaryl coupling. This allowed the rapid and reliable production of a series of substituted aminodibenzoxepines. A chelate model was proposed to account for the diastereoselectivity observed in the Grignard addition step.

  DOI：

  10.1021/jo900632a