| 913566-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• CAS: 913566-73-1
• 化学式: C₂₈H₃₀N₂O₆
• 分子量: 490.556
• InChiKey: DYMIUOHZVKQFRB-QGHQMRJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (S)-1-benzyl-5-(α-diazoacetoxy)piperidin-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  Nonracemic Bicyclic Lactam Lactones via Regio- and cis-Diastereocontrolled C−H Insertion. Asymmetric Synthesis of (8S,8aS)-Octahydroindolizidin-8-ol and (1S,8aS)-Octahydroindolizidin-1-ol

  摘要：

  The Rh-2(MPPIM)(4)-catalyzed intraniolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one proceeds with high regioselectivity and cis-diastereoselectivity to give good yields of chiral nonracemic bicyclic lactam lactones (BLLs). For (S)- and (R)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one, the regio selectivity of the C-H insertion is catalyst-dependent; for example, (S)-1-benzyl-5-(alpha-diazoacetoxy)piperidin-2-one undergoes C-H insertion at C-6 preferentially when Rh-2(5S-MPPIM)(4) is used, but with Rh-2(5R-MPPIM)(4), C-H insertion occurs preferentially at C-4. This effect is not observed in the reaction of (S)-1-benzyl-4-(alpha-diazoacetoxy)pyrrolidin-2-one. The utility of the BLLs as chiral building blocks in alkaloid synthesis is exemplified by the synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

  DOI：

  10.1021/jo901790g