benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate | 1019335-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate
• 英文别名: benzyl 2-oxo-2λ4-thia-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS: 1019335-03-5
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: CWJJUVCLNKTXBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate 在 sodium acetate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 0.5h， 以1.09 g的产率得到(2RS,4SR)-4-(benzyloxycarbonylamino)cyclopent-2-enyl (2RS,4SR)-4-(benzyloxycarbonylamino)cyclopent-2-ene-1-sulfonothioate
  参考文献：
  名称：

  3-Oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylates: the first isolation and characterization

  摘要：

  Methyl and benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate were isolated at rt and characterized for the first time. Both endo and exo-isomers were observed. Under suitable experimental conditions (stoichiometric amount of sodium acetate, -40 degrees C or sodium borohydride/methyl iodide) ring opening of these compounds gave the corresponding thiosulfonates or methyl sulfides, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.139
• 作为产物：
  描述：

  氨基甲酸苄酯 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 24.0h， 生成 benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate
  参考文献：
  名称：

  3-Oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylates: the first isolation and characterization

  摘要：

  Methyl and benzyl 3-oxo-3-thia-2-azabicyclo[2.2.1]hept-5-en-2-carboxylate were isolated at rt and characterized for the first time. Both endo and exo-isomers were observed. Under suitable experimental conditions (stoichiometric amount of sodium acetate, -40 degrees C or sodium borohydride/methyl iodide) ring opening of these compounds gave the corresponding thiosulfonates or methyl sulfides, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.139