2-methyl-5a,6,7,8,9,9a-hexahydro-5H-10-oxa-5-aza-dibenzo[a,d]cyclohepten-11-one | 1402836-44-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methyl-5a,6,7,8,9,9a-hexahydro-5H-10-oxa-5-aza-dibenzo[a,d]cyclohepten-11-one
• 英文别名: 2-methyl-5a,6,7,8,9,9a-hexahydrodibenzo[b,e][1,4]oxazepin-11(5H)-one；8-methyl-2,3,4,4a,11,11a-hexahydro-1H-benzo[b][4,1]benzoxazepin-6-one
• CAS: 1402836-44-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: KSKQGFXYXAVMIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 氧化环己烯 在 lithium bromide 作用下， 反应 0.08h， 以84%的产率得到2-methyl-5a,6,7,8,9,9a-hexahydro-5H-10-oxa-5-aza-dibenzo[a,d]cyclohepten-11-one
  参考文献：
  名称：

  Click Reaction of Epoxides with Anthranilic Acids Using Neat Grinding To Access Benzoxazepines

  摘要：

  An atom-economic, efficient, rapid (5 min), and highly regioselective one-pot click reaction has been developed for the synthesis of benzo[e][1,4]oxazepin-5-ones in excellent yields (78-92%). The method involves epoxide ring-opening-ring-closing cascade with anthranilic acids using neat grinding at room temperature in the presence of lithium bromide as a mild catalyst. In this procedure, pure products are obtained simply by washing the reaction mixture with warm water, thus hazardous solvents, tedious workup processes, and purification steps, such as column chromatography and recrystallization, are avoided.

  DOI：

  10.1055/s-0031-1290988

文献信息

• Facile Synthesis for Benzo-1,4-Oxazepine Derivatives by Tandem Transformation of C-N Coupling/C-H Carbonylation
  作者：Xiaojia Zhao、Jiong Zhang、Zeqin Zheng、Runsheng Xu

  DOI：10.3390/molecules22010053

  日期：——

  A tandem transformation of C-N coupling/C-H carbonylation has been developed for the synthesis of benzo-1,4-oxazepine pharmaceutically derivatives. Notably, this reaction was accomplished by various phenylamine with ally halides under carbon dioxide atmosphere employing 2-(2-dimethylamino-vinyl)-1H-inden-1-olcatalyzed. Furthermore, under the optimized conditions, various benzo-1,4-oxazepine derivatives

  已经开发了CN偶联/ CH羰基化的串联转化，用于合成苯并-1,4-氧杂ze庚因药物衍生物。值得注意的是，该反应是通过在2-（2-二甲基氨基-乙烯基）-1H-茚满-1-醇催化下在二氧化碳气氛下用各种苯胺与烯丙基卤完成的。此外，在优化的条件下，以良好的收率获得了各种苯并-1,4-氧杂氮杂卓衍生物。最后，提出了一种可行的CN偶联/ CH羰基化转化的CuI / CuIII机理。
• Click Reaction of Epoxides with Anthranilic Acids Using Neat Grinding To Access Benzoxazepines
  作者：Lal Yadav、Atul Singh、Ruchi Chawla

  DOI：10.1055/s-0031-1290988

  日期：2012.8

  An atom-economic, efficient, rapid (5 min), and highly regioselective one-pot click reaction has been developed for the synthesis of benzo[e][1,4]oxazepin-5-ones in excellent yields (78-92%). The method involves epoxide ring-opening-ring-closing cascade with anthranilic acids using neat grinding at room temperature in the presence of lithium bromide as a mild catalyst. In this procedure, pure products are obtained simply by washing the reaction mixture with warm water, thus hazardous solvents, tedious workup processes, and purification steps, such as column chromatography and recrystallization, are avoided.