ethyl 3a-hydroxy-2-oxo-3,3a-dihydro-2H-cyclopenta[l]phenanthrene-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ethyl 3a-hydroxy-2-oxo-3,3a-dihydro-2H-cyclopenta[l]phenanthrene-1-carboxylate
• 英文别名: ethyl (3aS)-3a-hydroxy-2-oxo-3H-cyclopenta[l]phenanthrene-1-carboxylate
• 化学式: C₂₀H₁₆O₄
• 分子量: 320.345
• InChiKey: YTOOYUZPAMWUQM-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 菲醌 在 1-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]-3-(4-methylphenyl)sulfonylurea 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 ethyl 3a-hydroxy-2-oxo-3,3a-dihydro-2H-cyclopenta[l]phenanthrene-1-carboxylate 、 ethyl 3a-hydroxy-2-oxo-3,3a-dihydro-2H-cyclopenta[l]phenanthrene-1-carboxylate
  参考文献：
  名称：

  Regioselectivity-Reversed Asymmetric Aldol Reaction of 1,3-Dicarbonyl Compounds

  摘要：

  Reverse regioselectivity: The first catalytic asymmetric C-1 functionalization of 1,3-dicarbonyl compounds by an aldol reaction is described, which regioselectively affords 6-hydroxyhexane-2,4-dione derivatives as the only product with high optical purity of up to 93 % ee. Furthermore, this method provides a facile access to enantioenriched oxygen-containing spirooxindoles and spirobutyrolactones from simple commercial available starting materials (see scheme).

  DOI：

  10.1002/chem.201201874

文献信息

• Regioselectivity-Reversed Asymmetric Aldol Reaction of 1,3-Dicarbonyl Compounds
  作者：Hongxin Liu、Huayue Wu、Zhenli Luo、Jie Shen、Guowei Kang、Bidai Liu、Zhifu Wan、Jun Jiang

  DOI：10.1002/chem.201201874

  日期：2012.9.17

  Reverse regioselectivity: The first catalytic asymmetric C-1 functionalization of 1,3-dicarbonyl compounds by an aldol reaction is described, which regioselectively affords 6-hydroxyhexane-2,4-dione derivatives as the only product with high optical purity of up to 93 % ee. Furthermore, this method provides a facile access to enantioenriched oxygen-containing spirooxindoles and spirobutyrolactones from simple commercial available starting materials (see scheme).