(2S,4R,5R,6S)-2-benzylsulfanyl-5-nitro-4-phenylspiro[5.5]undecan-10-one | 1604771-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R,5R,6S)-2-benzylsulfanyl-5-nitro-4-phenylspiro[5.5]undecan-10-one
• CAS: 1604771-31-4
• 化学式: C₂₄H₂₇NO₃S
• 分子量: 409.549
• InChiKey: RTAPXPIVENNSQQ-KEZOAJOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 四甲基胍 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(2S,4R,5R,6S)-2-benzylsulfanyl-5-nitro-4-phenylspiro[5.5]undecan-10-one
  参考文献：
  名称：

  Direct Remote Asymmetric Bisvinylogous 1,4-Additions of Cyclic 2,5-Dienones to Nitroalkenes

  摘要：

  Here we report that cyclic 2,5-dienones can act as bisvinylogous precursors through in situ generation of linear trienamine species with a cinchona-derived primary amine, and exclusively remote epsilon-regioselective 1,4-additions to nitro-alkenes were accomplished in moderate to high enantioselectivity. Moreover, a diversity of complex spirocyclic frameworks could be efficiently constructed in an enantioenriched manner from these multifunctional 1,4-adducts via subsequent vinylogous iminium and even cascade iminium catalysis of the same amine.

  DOI：

  10.1021/ol500700d

文献信息

• Direct Remote Asymmetric Bisvinylogous 1,4-Additions of Cyclic 2,5-Dienones to Nitroalkenes
  作者：Zhi Zhou、Xin Feng、Xiang Yin、Ying-Chun Chen

  DOI：10.1021/ol500700d

  日期：2014.5.2

  Here we report that cyclic 2,5-dienones can act as bisvinylogous precursors through in situ generation of linear trienamine species with a cinchona-derived primary amine, and exclusively remote epsilon-regioselective 1,4-additions to nitro-alkenes were accomplished in moderate to high enantioselectivity. Moreover, a diversity of complex spirocyclic frameworks could be efficiently constructed in an enantioenriched manner from these multifunctional 1,4-adducts via subsequent vinylogous iminium and even cascade iminium catalysis of the same amine.