(4R,5S)-1,5-Dimethyl-3-((2S,3R)-3-methyl-6-naphthalen-1-yl-3,4-dihydro-2H-pyran-2-yl)-4-phenyl-imidazolidin-2-one | 256382-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4R,5S)-1,5-Dimethyl-3-((2S,3R)-3-methyl-6-naphthalen-1-yl-3,4-dihydro-2H-pyran-2-yl)-4-phenyl-imidazolidin-2-one
• 英文别名: (4R,5S)-1,5-dimethyl-3-[(2S,3R)-3-methyl-6-naphthalen-1-yl-3,4-dihydro-2H-pyran-2-yl]-4-phenylimidazolidin-2-one
• CAS: 256382-71-5
• 化学式: C₂₇H₂₈N₂O₂
• 分子量: 412.532
• InChiKey: SWUDXIHMIXXYMB-LLLVADJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-Dimethyl-3-((2S,3R)-3-methyl-6-naphthalen-1-yl-3,4-dihydro-2H-pyran-2-yl)-4-phenyl-imidazolidin-2-one 在 间氯过氧苯甲酸 作用下， 以 phosphate buffer 、 二氯甲烷 为溶剂， 反应 18.0h， 以75%的产率得到(4S,5R)-1-((3R,5S)-5,6-Dihydroxy-3-methyl-6-naphthalen-1-yl-tetrahydro-pyran-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  路易斯酸介导的异头脲取代基立体选择性去除

  摘要：

  此处描述了第一个路易斯酸介导的异头手性脲基团或缺电子氮取代基的立体选择性去除。去除作为手性助剂的尿素基团的能力，以及内环烯烃的立体选择性硼氢化-氧化，使得来自手性烯丙酰胺杂[4+2]环加成的吡喃环加成物成为有用的手性模板。这代表了一种合成复杂吡喃杂环或 C-糖苷衍生物的新方法。

  DOI：

  10.1055/s-2003-38747
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-3-[(2S)-3-methylidene-6-naphthalen-1-yl-4H-pyran-2-yl]-4-phenylimidazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以90%的产率得到(4R,5S)-1,5-Dimethyl-3-((2S,3R)-3-methyl-6-naphthalen-1-yl-3,4-dihydro-2H-pyran-2-yl)-4-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  Studies on a Urea-Directed Stork−Crabtree Hydrogenation. Synthesis of the C1−C9 Subunit of (+)-Zincophorin

  摘要：

  [GRAPHICS]A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddition of chiral allenamides in natural product synthesis. The C1-C9 subunit matches Cossy's intermediate, thereby constituting a formal total synthesis. In addition, details of an unusual urea-directed Stork-Crabtree hydrogenation observed during these efforts are also disclosed here.

  DOI：

  10.1021/jo7017922

文献信息

• A Formal Total Synthesis of (+)-Zincophorin. Observation of an Unusual Urea-Directed Stork−Crabtree Hydrogenation
  作者：Zhenlei Song、Richard P. Hsung

  DOI：10.1021/ol070791a

  日期：2007.5.1

  A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.