N-(5-chlorobenzo[d][1,3]oxathiol-2-ylidene)benzenamine | 1161079-34-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: N-(5-chlorobenzo[d][1,3]oxathiol-2-ylidene)benzenamine
• 英文别名: N-(5-chlorobenzo[d][1,3]oxathiol-2-ylidene)aniline；5-chloro-N-phenyl-1,3-benzoxathiol-2-imine
• CAS: 1161079-34-0
• 化学式: C₁₃H₈ClNOS
• 分子量: 261.732
• InChiKey: IHTXQIFTWXUOEH-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  407.2±47.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 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：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-碘苯酚 、 硫代异氰酸苯酯 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以52%的产率得到N-(5-chlorobenzo[d][1,3]oxathiol-2-ylidene)benzenamine
  参考文献：
  名称：

  铜（I）催化一锅从邻碘苯酚和异硫氰酸酯合成2-亚氨基苯并-1,3-氧杂硫醇

  摘要：

  已经开发了通过铜（I）催化的一锅级联方法从易于获得的前体中新型有效形成2-亚氨基苯并-1,3-氧硫醇的方法。可以方便地以良好至优异的产率合成各种在药物和生化领域有用的2-亚氨基苯并-1,3-氧杂硫醇。

  DOI：

  10.1002/adsc.200800461

文献信息

• 2-亚胺-1,3-氧硫杂环戊烯类化合物的合成方法
  申请人：安徽师范大学

  公开号：CN103772348B

  公开（公告）日：2016-01-06

  本发明提供了一种2-亚胺-1,3-氧硫杂环戊烯类化合物的合成方法,将2-碘苯酚类化合物、异硫氰酸酯类化合物、碱、铜盐、N,N,N’N’-四甲基乙二胺和水混合，在室温搅拌，反应1-8小时，反应结束后用乙酸乙酯萃取，合并有机层，再用无水硫酸钠干燥，减压浓缩，得粗产物，粗产物经柱层析分离提纯，即得所需的2-苯并亚胺-1,3-氧硫杂苯并环戊烯类化合物。与现有技术相比，本发明使用水作溶剂，环境友好；在室温下即可反应，节能环保；利用“一锅法”短时间内直接得到目标产物，无副产物的生成，且无需惰性气体保护，操作更简单；反应高效，产率高达95%，更有利其工业化生产。
• 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>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
• 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)-Catalyzed One-Pot Synthesis of 2-Iminobenzo- 1,3-oxathioles from<i>ortho</i>-Iodophenols and Isothiocyanates
  作者：Xin Lv、Yunyun Liu、Weixing Qian、Weiliang Bao

  DOI：10.1002/adsc.200800461

  日期：2008.11.3

  A novel and efficient formation of 2-iminobenzo-1,3-oxathioles from readily available precursors via a copper(I)-catalyzed one-pot cascade process has been developed. Various 2-iminobenzo-1,3-oxathioles, which might be useful in pharmaceutical and biochemical areas, were conveniently synthesized in good to excellent yields.

  已经开发了通过铜（I）催化的一锅级联方法从易于获得的前体中新型有效形成2-亚氨基苯并-1,3-氧硫醇的方法。可以方便地以良好至优异的产率合成各种在药物和生化领域有用的2-亚氨基苯并-1,3-氧杂硫醇。