7-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione | 1582289-51-7

• 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: 7-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
• 英文别名: 7-Methyl-3-prop-1-en-2-yl-2,3-benzoxazine-1,4-dione；7-methyl-3-prop-1-en-2-yl-2,3-benzoxazine-1,4-dione
• CAS: 1582289-51-7
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: FHGQDAOZMZNXDH-UHFFFAOYSA-N

物化性质

• 沸点：
  354.1±35.0 °C(predicted)
• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione 、 7-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione 在 atmosphere 作用下， 反应 336.0h， 生成 6-methyl-1H-2,3-benzoxazine-1,4(3H)-dione 、 7-methyl-1H-2,3-benzoxazine-1,4(3H)-dione
  参考文献：
  名称：

  Synthesis of 3,5-Isoxazolidinediones and 1H-2,3-Benzoxazine-1,4(3H)-diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides

  摘要：

  The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a-f) and 2,2;-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a-f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a-e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a-e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.

  DOI：

  10.1021/jo402708j
• 作为产物：
  描述：

  4-methylphthaloyl chloride 、 丙酮肟 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 6-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione 、 7-methyl-3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
  参考文献：
  名称：

  Synthesis of 3,5-Isoxazolidinediones and 1H-2,3-Benzoxazine-1,4(3H)-diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides

  摘要：

  The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a-f) and 2,2;-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a-f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a-e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a-e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.

  DOI：

  10.1021/jo402708j

文献信息

• Synthesis of 3,5-Isoxazolidinediones and 1<i>H</i>-2,3-Benzoxazine-1,4(3<i>H</i>)-diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides
  作者：Robert A. Izydore、Joseph T. Jones、Benjamin Mogesa、Ira N. Swain、Ronda G. Davis-Ward、Dwayne L. Daniels、Felicia Frazier Kpakima、Sharnelle T. Spaulding-Phifer

  DOI：10.1021/jo402708j

  日期：2014.4.4

  The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a-f) and 2,2;-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a-f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a-e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a-e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.