4-chloro-N-(5-methylbenzo[d][1,3]oxathiol-2-ylidene)benzenamine | 1294010-10-8

• 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: 4-chloro-N-(5-methylbenzo[d][1,3]oxathiol-2-ylidene)benzenamine
• 英文别名: 4-chloro-N-(5-methylbenzo[d][1,3]oxathiol-2-ylidene)aniline；N-(4-chlorophenyl)-5-methyl-1,3-benzoxathiol-2-imine
• CAS: 1294010-10-8
• 化学式: C₁₄H₁₀ClNOS
• 分子量: 275.759
• InChiKey: ZKXTYDRVNZGKGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘-4-甲基苯酚 、 4-氯异硫氰酸苯酯 在 copper(II) nitrate trihydrate 、 四甲基乙二胺 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 4.0h， 以99%的产率得到4-chloro-N-(5-methylbenzo[d][1,3]oxathiol-2-ylidene)benzenamine
  参考文献：
  名称：

  铜/ N，N，N'，N'四甲基乙二胺催化的合成ñ -取代Benzoheterocycles经由CS交叉耦合在水环境温度

  摘要：

  AbstractCopper/N,N,N′,N′‐tetramethylethylenediamine (Cu/TMEDA)‐catalyzed ambient temperature tandem reactions of isothiocyanates with 2‐iodophenols or 2‐iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2‐iminobenzo‐1, 3‐ oxathioles and 2‐aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (<1 mol%) and can yield the products on a gram scale.magnified image

  DOI：

  10.1002/adsc.201400043

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.
• Copper/<i>N,N,N′,N′</i>-Tetramethylethylenediamine-Catalyzed Synthesis of<i>N</i>-Substituted Benzoheterocycles<i>via</i>CS Cross- Coupling at Ambient Temperature in Water
  作者：Na Zhao、Liang Liu、Fei Wang、Jia Li、Wu Zhang

  DOI：10.1002/adsc.201400043

  日期：2014.8.11

  AbstractCopper/N,N,N′,N′‐tetramethylethylenediamine (Cu/TMEDA)‐catalyzed ambient temperature tandem reactions of isothiocyanates with 2‐iodophenols or 2‐iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2‐iminobenzo‐1, 3‐ oxathioles and 2‐aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (<1 mol%) and can yield the products on a gram scale.magnified image