1-butoxy-2-methoxy-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline | 1160872-99-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 1-butoxy-2-methoxy-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline
• CAS: 1160872-99-0
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: ZFDALPDXVHZLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-butoxy-2-methoxy-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以96%的产率得到19-Butoxy-18-methoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
  参考文献：
  名称：

  (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners

  摘要：

  C1 and flexible analogs of (+/-)-nantenine were synthesized and evaluated for antagonist activity at human 5-HT(2)A receptors in a calcium mobilization assay. This work has resulted in the identification of the most potent 5-HT2A antagonist known based on an aporphine. Our results also suggest that the C1 position may be a key site for increasing 5-HT2A antagonist activity in this compound series. In addition, the structural rigidity of the aporphine core appears to be required for nantenine to function as a 5-HT2A antagonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.048
• 作为产物：
  描述：

  ethyl 1-butoxy-2-methoxy-4,5,6a,7-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline-6-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91%的产率得到1-butoxy-2-methoxy-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline
  参考文献：
  名称：

  (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners

  摘要：

  C1 and flexible analogs of (+/-)-nantenine were synthesized and evaluated for antagonist activity at human 5-HT(2)A receptors in a calcium mobilization assay. This work has resulted in the identification of the most potent 5-HT2A antagonist known based on an aporphine. Our results also suggest that the C1 position may be a key site for increasing 5-HT2A antagonist activity in this compound series. In addition, the structural rigidity of the aporphine core appears to be required for nantenine to function as a 5-HT2A antagonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.048