[(1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-3-bicyclo[3.1.1]heptanyl] 3-oxobutanoate | 136003-10-6

• 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: [(1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-3-bicyclo[3.1.1]heptanyl] 3-oxobutanoate
• CAS: 136003-10-6
• 化学式: C₂₇H₂₈O₃
• 分子量: 400.518
• InChiKey: OFRHFHWXVZWPJJ-IUGKGNRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-3-bicyclo[3.1.1]heptanyl] 3-oxobutanoate 在 zinc borohydride 作用下， 以 乙醚 为溶剂， 生成 3-Hydroxy-butyric acid (1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]hept-3-yl ester
  参考文献：
  名称：

  New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-esters

  摘要：

  3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from beta-pinene 4 - were reduced with zinc borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.

  DOI：

  10.1016/s0957-4166(00)82117-5
• 作为产物：
  描述：

  9-((1R,5S)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-phenanthrene 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 [(1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-3-bicyclo[3.1.1]heptanyl] 3-oxobutanoate
  参考文献：
  名称：

  New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-esters

  摘要：

  3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from beta-pinene 4 - were reduced with zinc borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.

  DOI：

  10.1016/s0957-4166(00)82117-5

文献信息

• Asymmetric Friedel - Crafts Reaction: An Application to the Synthesis of an Etodolac Analogue
  作者：L. M. Cabral、P. R. R. Costa、M. L. A. A. Vasconcellos、E. J. Barreiro、R. N. Castr

  DOI：10.1080/00397919608003781

  日期：1996.10

  Abstract An Etodolac analogue, (-)-7, was prepared in 40% ee. by asymmetric Friedel-Crafts reaction, involving tryptophol 4 and chiral β-ketobutyrate 5f, followed by hydrolysis.

  摘要 在 40% ee 中制备了 Etodolac 类似物 (-)-7。通过不对称 Friedel-Crafts 反应，涉及色氨酸 4 和手性 β-酮丁酸酯 5f，然后水解。