N-(benzo[d][1,3]oxathiol-2-ylidene)-2-methylbenzenamine | 1161079-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(benzo[d][1,3]oxathiol-2-ylidene)-2-methylbenzenamine
• 英文别名: N-(benzo[d][1,3]oxathiol-2-ylidene)-2-methylaniline
• CAS: 1161079-18-0
• 化学式: C₁₄H₁₁NOS
• 分子量: 241.313
• InChiKey: NQUDBTYUYYXQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-碘苯酚 、 邻甲苯异硫氰酸酯 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88%的产率得到N-(benzo[d][1,3]oxathiol-2-ylidene)-2-methylbenzenamine
  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

• 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.