ethyl 6-hydroxyimino-6-phenylhexanoate | 111742-93-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 6-hydroxyimino-6-phenylhexanoate
• CAS: 111742-93-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: AWRAXGDNQXYTRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-hydroxyimino-6-phenylhexanoate 在 镍 盐酸 、 sodium hydroxide 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 hexahydro-7-phenyl-1H-azepin-2-one
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives

  摘要：

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.

  DOI：

  10.1021/jm00397a027
• 作为产物：
  描述：

  乙基6-氧代-6-苯基己烷酸酯 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 ethyl 6-hydroxyimino-6-phenylhexanoate
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives

  摘要：

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.

  DOI：

  10.1021/jm00397a027

文献信息

• Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives
  作者：Hiroaki Yanagisawa、Sadao Ishihara、Akiko Ando、Takuro Kanazaki、Shuichi Miyamoto、Hiroyuki Koike、Yasuteru Iijima、Kiyoshi Oizumi、Yoichi Matsushita、Tadashi Hata

  DOI：10.1021/jm00397a027

  日期：1988.2

  alpha-[(3S)-3-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2-oxo-6 or 7-phenylperhydroazepin-1-yl]acetic acids (monoester monoacids) and their dicarboxylic acids were synthesized, and their angiotensin-converting enzyme (ACE) inhibitory activities were evaluated. The dicarboxylic acids having phenyl substituents at the 6R, 6S, and 7S positions on the azepinone ring showed potent inhibition in vitro. The corresponding monoester monoacids, when administered orally, suppressed the pressor response to angiotensin I administered intravenously. The monoester monoacids having the phenyl substituent at the 6-position showed a longer duration of action than one having the substituent at the 7-position. The structure-activity relationship was studied on the basis of the conformational energy calculation.