Ethyl 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate | 1158650-46-4

• 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: Ethyl 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate
• 英文别名: ethyl 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate
• CAS: 1158650-46-4
• 化学式: C₂₂H₂₃NO₆
• 分子量: 397.428
• InChiKey: INWPFESVDWDQAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-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(+/-)-Nornantenine
  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-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以88%的产率得到Ethyl 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate
  参考文献：
  名称：

  微波辅助直接联芳偶联：首次应用于阿朴啡合成

  摘要：

  我们研究了微波在直接联芳基偶联反应中用于合成阿朴啡生物碱 nantenine 类似物的用途。我们的研究表明，使用这种方法可以从苄基四氢异喹啉底物快速获得阿朴啡核心。这是阿朴啡分子合成中微波辅助直接联芳基偶联反应的首次报道。

  DOI：

  10.1016/j.tetlet.2009.03.029

文献信息

• (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners
  作者：Sandeep Chaudhary、Stevan Pecic、Onica LeGendre、Hérnan A. Navarro、Wayne W. Harding

  DOI：10.1016/j.bmcl.2009.03.048

  日期：2009.5

  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.
• Microwave-assisted direct biaryl coupling: first application to the synthesis of aporphines
  作者：Sandeep Chaudhary、Stevan Pecic、Onica LeGendre、Wayne W. Harding

  DOI：10.1016/j.tetlet.2009.03.029

  日期：2009.5

  microwaves in a direct biaryl coupling reaction for the synthesis of analogs of the aporphine alkaloid nantenine. Our study shows that the aporphine core may be rapidly accessed from benzyl-tetrahydroisoquinoline substrates with this method. This is the first report of a microwave-assisted direct biaryl coupling reaction in the synthesis of aporphine molecules.

  我们研究了微波在直接联芳基偶联反应中用于合成阿朴啡生物碱 nantenine 类似物的用途。我们的研究表明，使用这种方法可以从苄基四氢异喹啉底物快速获得阿朴啡核心。这是阿朴啡分子合成中微波辅助直接联芳基偶联反应的首次报道。