N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate | 217300-86-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate
• 英文别名: tert-butyl N-[2-[(E)-2-(2-nitrophenyl)ethenyl]phenyl]carbamate
• CAS: 217300-86-2
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: HFPUAFIAGUFYBD-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以2.05 g的产率得到2-[(E)-2-(2-硝基苯基)乙烯基]苯胺
  参考文献：
  名称：

  Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates

  摘要：

  The silane-induced cleavage of a series of N-p-tolylcarbamates and N-phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the Corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.

  DOI：

  10.1021/jo981816+
• 作为产物：
  描述：

  BOC-2-氨基苄醇 在 aluminum oxide 、 sodium hexamethyldisilazane 、 pyridinium chlorochromate 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成 N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate
  参考文献：
  名称：

  Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates

  摘要：

  The silane-induced cleavage of a series of N-p-tolylcarbamates and N-phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the Corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.

  DOI：

  10.1021/jo981816+