(Z)-3-[2-(3-bromophenyl)-2-oxoethylidene]-6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one | 1523436-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (Z)-3-[2-(3-bromophenyl)-2-oxoethylidene]-6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• 英文别名: (3Z)-3-[2-(3-bromophenyl)-2-oxoethylidene]-6-chloro-4H-1,4-benzoxazin-2-one
• CAS: 1523436-88-5
• 化学式: C₁₆H₉BrClNO₃
• 分子量: 378.609
• InChiKey: QEOHUNPNMFWQSU-JYRVWZFOSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  494.6±45.0 °C(predicted)
• 密度：
  1.685±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-[2-(3-bromophenyl)-2-oxoethylidene]-6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 以 苯 为溶剂， 反应 2.66h， 生成 (1S*,16R*)-14-(3-bromophenyl)-16-butoxy-7-chloro-3,15-dioxa-10-azatetracyclo[8.7.0.0^1,13.0^4,9]heptadeca-4,6,8,13-tetraene-2,11,12-trione 、 (1R*,16R*)-14-(3-bromophenyl)-16-butoxy-7-chloro-3,15-dioxa-10-azatetracyclo[8.7.0.0^1,13.0^4,9]heptadeca-4,6,8,13-tetraene-2,11,12-trione
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: XCVIII. [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids

  摘要：

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14-aryl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-triones. The structure of (1S*,16R*)-7-chloro-16-ethoxy-14-phenyl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-trione was determined by X-ray analysis. A new synthetic approach was developed to heteroanalogs of 13(14 -> 8)-abeo steroids, substituted 3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadecanes.

  DOI：

  10.1134/s1070428013120105
• 作为产物：
  描述：

  3-bromobenzoylpyruvic acid 、 4-氯-2-氨基苯酚 以 异丙醇 为溶剂， 反应 1.5h， 以81%的产率得到(Z)-3-[2-(3-bromophenyl)-2-oxoethylidene]-6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: XCVIII. [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids

  摘要：

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14-aryl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-triones. The structure of (1S*,16R*)-7-chloro-16-ethoxy-14-phenyl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-trione was determined by X-ray analysis. A new synthetic approach was developed to heteroanalogs of 13(14 -> 8)-abeo steroids, substituted 3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadecanes.

  DOI：

  10.1134/s1070428013120105