3,4-epoxy-2-piperidone | 956710-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧哌啶
• 英文名称: 3,4-epoxy-2-piperidone
• 英文别名: tedanalactam；7-Oxa-3-azabicyclo[4.1.0]heptan-2-one
• CAS: 956710-49-9
• 化学式: C₅H₇NO₂
• mdl: MFCD18822876
• 分子量: 113.116
• InChiKey: PHTVNQOAOFDDIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以 二氯甲烷 、 水 为溶剂， 以74%的产率得到3,4-epoxy-2-piperidone
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Tedanalactam

  摘要：

  The first stereoselective route providing access to both enantiomers of tedanalactam. a naturally occurring piperidone, has been developed. The stereogenic centers were generated by the use of Sharpless asymmetric dihydroxylation. Tandem oxidation-Wittig reaction and one-pot deprotection, lactamization, and oxirane ring formation are the other key elements.

  DOI：

  10.1021/jo901143b

文献信息

• Total Synthesis of (−)- and (+)-Tedanalactam
  作者：Mahesh S. Majik、Perunninakulath S. Parameswaran、Santosh G. Tilve

  DOI：10.1021/jo901143b

  日期：2009.8.21

  The first stereoselective route providing access to both enantiomers of tedanalactam. a naturally occurring piperidone, has been developed. The stereogenic centers were generated by the use of Sharpless asymmetric dihydroxylation. Tandem oxidation-Wittig reaction and one-pot deprotection, lactamization, and oxirane ring formation are the other key elements.