6-ethyl-8,9-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]-azepin-7(6H)-one | 1373332-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 6-ethyl-8,9-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]-azepin-7(6H)-one
• CAS: 1373332-86-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: HEEBRQCJRQEWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 6-ethyl-8,9-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]-azepin-7(6H)-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以44%的产率得到6-ethyl-8-pentyl-8,9-dihydro-5H-[1,3]dioxolo[4',5':4,5]-benzo[1,2-c]azepin-7(6H)-one
  参考文献：
  名称：

  Concise Synthesis of 2-Benzazepine Derivatives and Their Biological Activity

  摘要：

  2-Benzazepines, which are potentially good candidates for new drug therapies to treat skin wounds, were readily prepared from substituted cinnamylamide via an intramolecular Friedel Crafts reaction. With few steps and effective reactions, the procedure enables a rapid derivatization of 2-benzazepines. Moreover, optically active 4-substituted-2-benzazepines were prepared from chiral alpha-substituted cinnamylamides, which were readily prepared by asymmetric alpha-alkylation of chiral cinnamyl oxazolidinone amides. We have easily prepared a library of more than 20 derivatives and examined the biological activity of the compounds.

  DOI：

  10.1021/jo300380z
• 作为产物：
  描述：

  3-benzo[1,3]dioxol-5-yl-propionyl chloride 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 6-ethyl-8,9-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]-azepin-7(6H)-one
  参考文献：
  名称：

  Concise Synthesis of 2-Benzazepine Derivatives and Their Biological Activity

  摘要：

  2-Benzazepines, which are potentially good candidates for new drug therapies to treat skin wounds, were readily prepared from substituted cinnamylamide via an intramolecular Friedel Crafts reaction. With few steps and effective reactions, the procedure enables a rapid derivatization of 2-benzazepines. Moreover, optically active 4-substituted-2-benzazepines were prepared from chiral alpha-substituted cinnamylamides, which were readily prepared by asymmetric alpha-alkylation of chiral cinnamyl oxazolidinone amides. We have easily prepared a library of more than 20 derivatives and examined the biological activity of the compounds.

  DOI：

  10.1021/jo300380z