2β-methoxy-9,10-methylenedioxy-galanth-1(15)-ene | 109814-30-4

• 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: 2β-methoxy-9,10-methylenedioxy-galanth-1(15)-ene
• 英文别名: 2β-Methoxy-9,10-methylendioxy-galanth-1(15)-en；(15R,17S,19R)-17-methoxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9-tetraene
• CAS: 109814-30-4
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: PNVZKENNRSHOKG-YOIRWDDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (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 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以89%的产率得到2β-methoxy-9,10-methylenedioxy-galanth-1(15)-ene
  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

• Takeda; Kotera, Pharmaceutical Bulletin, 1957, vol. 5, p. 234,236
  作者：Takeda、Kotera

  DOI：——

  日期：——
• 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.