(15R,17S,19R)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9-tetraen-11-one | 1175589-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (15R,17S,19R)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9-tetraen-11-one
• CAS: 1175589-12-4
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: AMFYJOVDLJEARZ-CEFVDNRUSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  565.6±50.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (15R,17S,19R)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9-tetraen-11-one 、 trimethoxonium tetrafluoroborate 在 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以95%的产率得到(2S,3aR,3a1R)-2-methoxy-2,3,3a,3a1,4,5-hexahydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one
  参考文献：
  名称：

  Rapid and Enantioselective Assembly of the Lycorine Framework Using Chemoenzymatic Techniques

  摘要：

  The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.

  DOI：

  10.1021/ol901364n
• 作为产物：
  描述：

  2-((2R,4S,4aR)-4-hydroxy-6-oxo-2,4,4a,6-tetrahydro-3H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]chromen-2-yl)acetonitrile 在 氨 、 氢气 、 钴 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、3.0 MPa 条件下， 反应 3.0h， 以65%的产率得到(15R,17S,19R)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9-tetraen-11-one
  参考文献：
  名称：

  Rapid and Enantioselective Assembly of the Lycorine Framework Using Chemoenzymatic Techniques

  摘要：

  The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.

  DOI：

  10.1021/ol901364n

文献信息

• Rapid and Enantioselective Assembly of the Lycorine Framework Using Chemoenzymatic Techniques
  作者：Matthew T. Jones、Brett D. Schwartz、Anthony C. Willis、Martin G. Banwell

  DOI：10.1021/ol901364n

  日期：2009.8.6

  The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.