8-Methoxy-4-methyl-1,2,4,5-tetrahydro-2-benzazepin-3-one | 1144029-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 8-Methoxy-4-methyl-1,2,4,5-tetrahydro-2-benzazepin-3-one
• CAS: 1144029-14-0
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: SEOKFNNZYDWYNM-UHFFFAOYSA-N

物化性质

• 熔点：
  157.1-157.8 °C
• 沸点：
  413.6±45.0 °C(predicted)
• 密度：
  1.077±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 8-Methoxy-4-methyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到8-methoxy-4-methyl-2-pentyl-4,5-dihydro-1H-2-benzazepin-3-one
  参考文献：
  名称：

  An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity

  摘要：

  N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo5-methoxyphenylmethyl) methacrylamides. The structure and activity relationship of these derivatives are examined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.117
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 8-Methoxy-4-methyl-1,2,4,5-tetrahydro-2-benzazepin-3-one
  参考文献：
  名称：

  An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity

  摘要：

  N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo5-methoxyphenylmethyl) methacrylamides. The structure and activity relationship of these derivatives are examined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.117

文献信息

• Mechanistic study of 7-endo selective radical cyclization of the aryl radical
  作者：Akio Kamimura、Yuriko Ishihara、Masahiro So、Takahiro Hayashi

  DOI：10.1016/j.tetlet.2009.01.132

  日期：2009.4

  Mechanistic studies on the novel 7-endo selective radical cyclization were carried out. The reaction afforded three products, 7-endo product, 6-exo product, and reduced product. The distribution of these products was estimated by GC analyses. The 7-endo/6-exo selectivity was almost constant against variation in the concentration of Bu3SnH, while the reduction/cyclization ratio was sensitive to the concentration of Bu3SnH. The reduction/cyclization ratio was mainly affected by the rotational isomeric ratio of the cyclization precursor. Kinetic analyses indicated that the cyclization process should be irreversible, and the rate constant of 7-endo/6-exo radical cyclization was estimated to be about 3.3 x 10(8) s (1) at 80 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.
• An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity
  作者：Akio Kamimura、Masahiro So、Tomohiro Kuratani、Kenji Matsuura、Makoto Inui

  DOI：10.1016/j.bmcl.2009.04.117

  日期：2009.6

  N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo5-methoxyphenylmethyl) methacrylamides. The structure and activity relationship of these derivatives are examined. (C) 2009 Elsevier Ltd. All rights reserved.