(+/-)-2-(N-tert-butoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-en-3-one | 175651-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (+/-)-2-(N-tert-butoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-en-3-one
• 英文别名: tert-butyl 3-oxo-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 175651-10-2
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: IRFDNFACPYQHBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(N-tert-butoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-en-3-one 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (+/-)-cis-4-(hydroxymethyl)cyclohex-2-en-1-ylamine
  参考文献：
  名称：

  Deamination of 9-(Hydroxymethylated cycloalkyl)-9H-adenines (Carbocyclic Adenine Nucleosides) by Adenosine Deaminase: Effect of High-Pressure Upon Deamination Rate and Enantioselectivity

  摘要：

  The deamination of eight kinds of racemic carbocyclic adenine nucleosides by adenosine deaminase under high-pressure (400 MPa) was examined and the result was compared with that obtained from the reaction under atmospheric pressure. The deamination of all carbocyclic nucleosides irrespective to their ring size of carbocycles was facilitated remarkably by high-pressure. The reaction of three and five membered carbocyclic pressure whereas the enantioselectivity of six membered carbocyclic nucleosides was suppressed under high-pressure. However, the enantioselectivity of four membered nucleosides was low under both conditions.

  DOI：

  10.1080/07328319608002411
• 作为产物：
  描述：

  (+/-)-2-azabicyclo<2.2.2>oct-5-en-3-one 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以97%的产率得到(+/-)-2-(N-tert-butoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-en-3-one
  参考文献：
  名称：

  Deamination of 9-(Hydroxymethylated cycloalkyl)-9H-adenines (Carbocyclic Adenine Nucleosides) by Adenosine Deaminase: Effect of High-Pressure Upon Deamination Rate and Enantioselectivity

  摘要：

  The deamination of eight kinds of racemic carbocyclic adenine nucleosides by adenosine deaminase under high-pressure (400 MPa) was examined and the result was compared with that obtained from the reaction under atmospheric pressure. The deamination of all carbocyclic nucleosides irrespective to their ring size of carbocycles was facilitated remarkably by high-pressure. The reaction of three and five membered carbocyclic pressure whereas the enantioselectivity of six membered carbocyclic nucleosides was suppressed under high-pressure. However, the enantioselectivity of four membered nucleosides was low under both conditions.

  DOI：

  10.1080/07328319608002411