N-(benzo[d][1,3]oxathiol-2-ylidene)-4-nitrobenzenamine | 1294010-05-1

• 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: N-(benzo[d][1,3]oxathiol-2-ylidene)-4-nitrobenzenamine
• 英文别名: N-(4-nitrophenyl)-1,3-benzoxathiol-2-imine
• CAS: 1294010-05-1
• 化学式: C₁₃H₈N₂O₃S
• 分子量: 272.284
• InChiKey: UWEWLKLICKQVJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘苯酚 、 异硫代氰基4-硝基苯酯 在 三乙烯二胺 、 1,10-菲罗啉 、 copper dichloride 作用下， 以 水 为溶剂， 反应 24.0h， 以91%的产率得到N-(benzo[d][1,3]oxathiol-2-ylidene)-4-nitrobenzenamine
  参考文献：
  名称：

  Aqueous C–S cross-coupling: synthesis of 2-iminobenzo-1,3-oxathioles via CuCl2·H2O-catalyzed tandem reaction of 2-iodophenols with isothiocyanates

  摘要：

  A CuCl2 center dot H2O-catalyzed tandem reaction of 2-iodophenol with isothiocyanate in water is described, which provides an environmentally benign, efficient, and practical route for the generation of 2-iminobenzo-1,3-oxathiole. It was noteworthy that most of the products were easily separated from the reaction system by simple filtration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.061

文献信息

• Aqueous C–S cross-coupling: synthesis of 2-iminobenzo-1,3-oxathioles via CuCl2·H2O-catalyzed tandem reaction of 2-iodophenols with isothiocyanates
  作者：Qiuping Ding、Xianjin Liu、Banpeng Cao、Zhenzhen Zong、Yiyuan Peng

  DOI：10.1016/j.tetlet.2011.02.061

  日期：2011.4

  A CuCl2 center dot H2O-catalyzed tandem reaction of 2-iodophenol with isothiocyanate in water is described, which provides an environmentally benign, efficient, and practical route for the generation of 2-iminobenzo-1,3-oxathiole. It was noteworthy that most of the products were easily separated from the reaction system by simple filtration. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper(I)-catalyzed tandem reaction of 2-iodophenols with isothiocyanates in room temperature ionic liquids
  作者：Fang Yao、Wenyan Hao、Ming-Zhong Cai

  DOI：10.1016/j.jorganchem.2012.09.010

  日期：2013.1

  A copper(I)-catalyzed tandem reaction of 2-iodophenols with isothiocyanates in hydrophobic [ bmim] [PF6] ionic liquid was described, which proceeded smoothly and generated a variety of 2-iminobenzo-1,3-oxathioles in good to excellent yields. The tandem reaction that was carried out in [ bmim][ PF6] has some obvious advantages such as reaction rate acceleration and yield increasing as compared with the reaction run in volatile solvents such as toluene. Furthermore, the CuI/1,10-phenanthroline catalytic system can be reused up to 6 times without loss of activity and efficiency. (C) 2012 Elsevier B. V. All rights reserved.