ethyl (E)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-4-oxobut-2-enoate | 304467-45-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (E)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-4-oxobut-2-enoate
• CAS: 304467-45-6
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: NEMJBVHDMUULFX-MZDDGOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氨基邻苯二甲胺 、 ethyl (E)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-4-oxobut-2-enoate 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到ethyl 3-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decane-4-carbonyl]-1-(1,3-dioxoisoindol-2-yl)aziridine-2-carboxylate
  参考文献：
  名称：

  A Facile and Highly Diastereoselective Aziridination of Chiral Camphor N-Enoylpyrazolidinones with N-Aminophthalimide

  摘要：

  Reaction of various chiral camphor N-enoylprazalidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxilary can be easily recovered in high yields under mild reaction conditions.

  DOI：

  10.1021/jo005621p
• 作为产物：
  描述：

  富马酸单乙酯 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl (E)-4-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-4-oxobut-2-enoate
  参考文献：
  名称：

  A Facile and Highly Diastereoselective Aziridination of Chiral Camphor N-Enoylpyrazolidinones with N-Aminophthalimide

  摘要：

  Reaction of various chiral camphor N-enoylprazalidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxilary can be easily recovered in high yields under mild reaction conditions.

  DOI：

  10.1021/jo005621p

文献信息

• A Facile and Highly Diastereoselective Aziridination of Chiral Camphor <i>N</i>-Enoylpyrazolidinones with <i>N</i>-Aminophthalimide
  作者：Kung-Shuo Yang、Kwunmin Chen

  DOI：10.1021/jo005621p

  日期：2001.3.1

  Reaction of various chiral camphor N-enoylprazalidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxilary can be easily recovered in high yields under mild reaction conditions.