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 | 1175589-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 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
• CAS: 1175589-09-9
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: RFOZNCBUKGHMNE-KKUKJKQGSA-N

物化性质

• 沸点：
  649.6±55.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 6-[(3aR,6R,7aS)-6-(cyanomethyl)-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]-1,3-benzodioxole-5-carboxylate 在 水 、 溶剂黄146 作用下， 反应 1.0h， 以89%的产率得到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
  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