(4S,5R)-1-((S)-1-Benzenesulfonyl-5-methyl-3-methylene-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one | 765952-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-1-((S)-1-Benzenesulfonyl-5-methyl-3-methylene-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
• 英文别名: (4S,5R)-1-[(2S)-1-(benzenesulfonyl)-5-methyl-3-methylidene-2,4-dihydropyridin-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 765952-17-8
• 化学式: C₂₄H₂₇N₃O₃S
• 分子量: 437.563
• InChiKey: FOOOPPACFXCWAZ-AJSBUHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-((S)-1-Benzenesulfonyl-5-methyl-3-methylene-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 在 [Ir(cod)pyr(PCy₃)PF₆] 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 24.0h， 以37%的产率得到(4S,5R)-1-((2S,3S)-1-Benzenesulfonyl-3,5-dimethyl-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-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
• 作为产物：
  描述：

  2-methyl-1-<(phenylsulfonyl)imino>-2-propene 、 以 正己烷 为溶剂， 反应 15.0h， 生成 (4S,5R)-1-((S)-1-Benzenesulfonyl-5-methyl-3-methylene-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 、 (4S,5R)-1-((R)-1-Benzenesulfonyl-5-methyl-3-methylene-1,2,3,4-tetrahydro-pyridin-2-yl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  艾伦酰胺的反电子需求氮杂[4 + 2]环加成反应

  摘要：

  本文描述了烯丙酰胺与1-氮杂二烯的电子反需求氮杂-[4 + 2]环加成反应。说明了溶剂对非对映选择性的影响以及合成范围和机理的见解。尽管存在一些合成限制，但这种aza- [4 + 2]环加成的确为合成aza-糖苷相关的杂环提供了有用的模板。

  DOI：

  10.1016/j.tet.2004.05.117

文献信息

• Studies on a Urea-Directed Stork−Crabtree Hydrogenation. Synthesis of the C1−C9 Subunit of (+)-Zincophorin
  作者：Zhenlei Song、Richard P. Hsung、Ting Lu、Andrew G. Lohse

  DOI：10.1021/jo7017922

  日期：2007.12.1

  [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.
• Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides
  作者：Craig R. Berry、Richard P. Hsung

  DOI：10.1016/j.tet.2004.05.117

  日期：2004.8

  An inverse electron-demand aza-[4+2] cycloaddition reaction of allenamides with 1-azadiene is described here. Effects of solvents on diastereoselectivity along with synthetic scopes and mechanistic insights are illustrated. Despite some synthetic limitations, this aza-[4+2] cycloaddition does provide a useful template for the synthesis of aza-glycoside related heterocycles.

  本文描述了烯丙酰胺与1-氮杂二烯的电子反需求氮杂-[4 + 2]环加成反应。说明了溶剂对非对映选择性的影响以及合成范围和机理的见解。尽管存在一些合成限制，但这种aza- [4 + 2]环加成的确为合成aza-糖苷相关的杂环提供了有用的模板。