3,4-Epoxy-1,2,5,6-tetrahydropyridine | 286-21-5

• 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-1,2,5,6-tetrahydropyridine
• 英文别名: 7-Oxa-3-azabicyclo[4.1.0]heptane
• CAS: 286-21-5
• 化学式: C₅H₉NO
• mdl: MFCD13176275
• 分子量: 99.1326
• InChiKey: RHHCZFVZZLJFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-Epoxy-1,2,5,6-tetrahydropyridinium p-chlorobenzenesulfonate 在 magnesium sulfate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,4-Epoxy-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Epoxidation of Primary and Secondary Alkenylammonium Salts with Dimethyldioxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines

  摘要：

  Selective syn-epoxidation of C=C double bonds in primary and secondary alkenylammonium arenesulfonate salts 3H(+), to give the corresponding epoxyalkylammonium salts 4H(+), has been achieved by reaction with electrophilic O-transfer reagents such as m-CPBA, methyl(trifluoromethyl)dioxirane (TFDO), and dimethyldioxirane (DMDO). Epoxyalkylamines 4 are easily obtained in high yields from the corresponding epoxyalkylammonium salts 4H(+) by simple deprotonation with sodium carbonate. The ammonium group deactivates the C=C double bond, and hence the epoxidation rate is slower than in the case of simple olefins. II-Bonding interaction between the ammonium group and the O-transfer reagent(m-CPBA and DMDO) in the transition state is claimed to account for the rate enhancement and diastereoselectivity observed when the necessary conformational requirements are established. The allylic ammonium group is shown to be very efficient in directing the epoxidation with m-CPBA and DMDO on the syn-diastereoface.

  DOI：

  10.1021/jo00117a020