methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate | 1403665-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate
• 英文别名: methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-1H-3,1-benzoxazine-4-carboxylate
• CAS: 1403665-38-2
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: QWXYARXYHSRZIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙醇 、 methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate 在 盐酸 作用下， 反应 1.0h， 以95%的产率得到ethyl 4-(2-ethoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles

  摘要：

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.

  DOI：

  10.3987/com-12-12472
• 作为产物：
  描述：

  dimethyl 2-hydroxy-2-(2-(methoxycarbonylamino)phenyl)succinate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 192.0h， 以70%的产率得到methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles

  摘要：

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.

  DOI：

  10.3987/com-12-12472

文献信息

• Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles
  作者：Oscar R. Suárez-Castillo、Claudia I. Bautista-Hernández、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Araceli Sierra-Zenteno、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.3987/com-12-12472

  日期：——

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.