2-(benzo[d]thiazol-2-yl)-4-methoxyphenyl diethylcarbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-yl)-4-methoxyphenyl diethylcarbamate
• 英文别名: [2-(1,3-benzothiazol-2-yl)-4-methoxyphenyl] N,N-diethylcarbamate
• 化学式: C₁₉H₂₀N₂O₃S
• 分子量: 356.445
• InChiKey: FATDNHHIDFXQJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(benzo[d]thiazol-2-yl)-4-methoxyphenol 、 N,N-二乙基甲酰胺 在 叔丁基过氧化氢 、 copper diacetate 作用下， 以 水 为溶剂， 以78%的产率得到2-(benzo[d]thiazol-2-yl)-4-methoxyphenyl diethylcarbamate
  参考文献：
  名称：

  N，N-二取代甲酰胺和苯酚的铜催化交叉脱氢偶联：直接获得氨基甲酸酯

  摘要：

  AbstractAn efficient copper‐catalyzed protocol has been developed for the synthesis of carbamates from dialkylformamides and phenols possessing directing groups such as benzothiazole, quinoline and formyl at the ortho‐position. In this chelation assisted approach, CO bond formation takes place via a cross dehydrogenative coupling (CDC) between the formyl CH of dialkylformamide and phenolic OH in the presence of copper(II)acetate/aqueous tert‐butyl hydroperoxide. Under identical reaction conditions, salicylic acid derivatives underwent amidation with the carboxylic group rather than formamidation of the phenolic OH. The use of a cheap and environmentally benign catalyst along with the tolerance of a wide range of functional groups makes this an easy, phosgene‐free route to carbamates.magnified image

  DOI：

  10.1002/adsc.201400659

文献信息

• Copper-Catalyzed Cross Dehydrogenative Coupling of<i>N</i>,<i>N</i>-Disubstituted Formamides and Phenols: A Direct Access to Carbamates
  作者：Wajid Ali、Saroj K. Rout、Srimanta Guin、Anju Modi、Arghya Banerjee、Bhisma K. Patel

  DOI：10.1002/adsc.201400659

  日期：2015.2.9

  AbstractAn efficient copper‐catalyzed protocol has been developed for the synthesis of carbamates from dialkylformamides and phenols possessing directing groups such as benzothiazole, quinoline and formyl at the ortho‐position. In this chelation assisted approach, CO bond formation takes place via a cross dehydrogenative coupling (CDC) between the formyl CH of dialkylformamide and phenolic OH in the presence of copper(II)acetate/aqueous tert‐butyl hydroperoxide. Under identical reaction conditions, salicylic acid derivatives underwent amidation with the carboxylic group rather than formamidation of the phenolic OH. The use of a cheap and environmentally benign catalyst along with the tolerance of a wide range of functional groups makes this an easy, phosgene‐free route to carbamates.magnified image