8-(2-(Butylamino)ethyl)-3,5-dimethoxyphenanthrene-2,6-diol | 200049-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 8-(2-(Butylamino)ethyl)-3,5-dimethoxyphenanthrene-2,6-diol
• 英文别名: 8-[2-(butylamino)ethyl]-3,5-dimethoxyphenanthrene-2,6-diol
• CAS: 200049-32-7
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: KRGSTQDEZQNXOF-UHFFFAOYSA-N

物化性质

• 沸点：
  587.1±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 8-(2-(Butylamino)ethyl)-3,5-dimethoxyphenanthrene-2,6-diol 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以91%的产率得到N-butylnorlitebamine
  参考文献：
  名称：

  Litebamine N-Homologues:  Preparation and Anti-Acetylcholinesterase Activity

  摘要：

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).

  DOI：

  10.1021/np970298f
• 作为产物：
  描述：

  laurolitsine 在 ammonium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 8-(2-(Butylamino)ethyl)-3,5-dimethoxyphenanthrene-2,6-diol
  参考文献：
  名称：

  Litebamine N-Homologues:  Preparation and Anti-Acetylcholinesterase Activity

  摘要：

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).

  DOI：

  10.1021/np970298f

文献信息

• Preparation of phenanthrene alkaloids via solvolysis of 2-hydroxyaporphines
  作者：Shoei-Sheng Lee、Chi-Ming Chiou、Huey-Yi Lin、Chung-Hsiung Chen

  DOI：10.1016/0040-4039(95)00077-p

  日期：1995.2

  Phenanthrene alkaloids was semisynthesized fromN-alkyllaurolitsines such as boldine directly from solvolysis with 1M ammonium acetate under reflux overnight. This one step reaction is easily workup and the yield is high (> 80%).

  从N-烷基月桂氨酸类化合物（如丁二烯）中直接用1M乙酸铵在回流下的溶剂分解作用，半合成菲类生物碱。这一一步反应很容易后处理，收率很高（> 80％）。
• Litebamine <i>N</i>-Homologues:  Preparation and Anti-Acetylcholinesterase Activity
  作者：Chi-Ming Chiou、Jaw-Jou Kang、Shoei-Sheng Lee

  DOI：10.1021/np970298f

  日期：1998.1.1

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).