1-ethoxycarbonyl-1,2,5,6-tetrahydropyridine-3,5,5-d3 | 88239-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-ethoxycarbonyl-1,2,5,6-tetrahydropyridine-3,5,5-d3
• 英文别名: 1-ethoxycarbonyl-1,2,5,6-tetrahydropyridine-3,5,5-d₃
• CAS: 88239-54-7
• 化学式: C₈H₁₃NO₂
• 分子量: 158.173
• InChiKey: NXKRWPABPQRKFS-GRRZFFPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-ethoxycarbonyl-1,2,5,6-tetrahydropyridine-3,5,5-d3 在 sodium azide 、 ammonium chloride 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Synthesis and dynamic NMR studies of the 3,7-diazabicyclo[4.1.0]heptane system

  摘要：

  AbstractA new bicyclic system, 3,7‐diazabicyclo[4.1.0]heptane, has been prepared from 3‐(ethoxycarbonyl)‐7,3‐oxazabicyclo[4.1.0]heptane by reaction with sodium azide and reduction of the resulting tosyloxy azide with lithium aluminum hydride. The molecule can exist in four stereoisomeric half‐chairs, depending on the configuration of the two nitrogen atoms. Half‐chair ring reversal and piperidine nitrogen inversion are fast on the NMR time scale at all observed temperatures. Inversion of the secondary aziridine nitrogen becomes slow as the temperature is lowered (Tc= −10°C). Complete analysis of the 1H spectrum was possible with the 1,5,5‐trideuteriated analog. At slow exchange, two aziridine invertomers are present with an exo/endo ratio of approximately 0.7 in toluene‐d8, 0.7 in CH2Cl2 and 1.7 in CHCl3/CH2Cl2. The free energy of activation for nitrogen inversion is 13.2 kcal mol−1 at −10°C in CHCl3/CH2Cl2.

  DOI：

  10.1002/omr.1270210904
• 作为产物：
  描述：

  1-(苯基甲基)-4-哌啶-3,3,5,5-d4-醇 在 potassium tert-butylate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 25.0h， 生成 1-ethoxycarbonyl-1,2,5,6-tetrahydropyridine-3,5,5-d3
  参考文献：
  名称：

  Synthesis and dynamic NMR studies of the 3,7-diazabicyclo[4.1.0]heptane system

  摘要：

  AbstractA new bicyclic system, 3,7‐diazabicyclo[4.1.0]heptane, has been prepared from 3‐(ethoxycarbonyl)‐7,3‐oxazabicyclo[4.1.0]heptane by reaction with sodium azide and reduction of the resulting tosyloxy azide with lithium aluminum hydride. The molecule can exist in four stereoisomeric half‐chairs, depending on the configuration of the two nitrogen atoms. Half‐chair ring reversal and piperidine nitrogen inversion are fast on the NMR time scale at all observed temperatures. Inversion of the secondary aziridine nitrogen becomes slow as the temperature is lowered (Tc= −10°C). Complete analysis of the 1H spectrum was possible with the 1,5,5‐trideuteriated analog. At slow exchange, two aziridine invertomers are present with an exo/endo ratio of approximately 0.7 in toluene‐d8, 0.7 in CH2Cl2 and 1.7 in CHCl3/CH2Cl2. The free energy of activation for nitrogen inversion is 13.2 kcal mol−1 at −10°C in CHCl3/CH2Cl2.

  DOI：

  10.1002/omr.1270210904