methyl (3aR,6S,7R,7aS)-6-(cyanomethyl)-7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-[4,5'-bibenzo[d][1,3]dioxole]-6'-carboxylate | 1175589-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: methyl (3aR,6S,7R,7aS)-6-(cyanomethyl)-7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-[4,5'-bibenzo[d][1,3]dioxole]-6'-carboxylate
• CAS: 1175589-18-0
• 化学式: C₂₀H₂₁NO₇
• 分子量: 387.389
• InChiKey: QUVXIXNXVGBDRH-GKMAIYAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107.24
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (3aR,6S,7R,7aS)-6-(cyanomethyl)-7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-[4,5'-bibenzo[d][1,3]dioxole]-6'-carboxylate 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以82%的产率得到
  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-[(3aS,4R,5S,7aS)-7-bromo-4-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]acetonitrile 、 methyl 6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzo[d][1,3]dioxole-5-carboxylate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以79%的产率得到methyl (3aR,6S,7R,7aS)-6-(cyanomethyl)-7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-[4,5'-bibenzo[d][1,3]dioxole]-6'-carboxylate
  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