2-((difluoromethyl)thio)-1H-benzo[d]imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-((difluoromethyl)thio)-1H-benzo[d]imidazole
• 英文别名: 2-Difluoromethylthiobenzimidazole；2-[(difluoromethyl)thio]-1H-benzimidazole；2-(difluoromethylsulfanyl)-1H-benzimidazole
• 化学式: C₈H₆F₂N₂S
• mdl: MFCD00518586
• 分子量: 200.212
• InChiKey: GUCODYJAVBMOPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate 、 1H-苯并咪唑-2-硫醇 在 lithium hydroxide 作用下， 以 氟苯 为溶剂， 反应 0.5h， 以63%的产率得到2-((difluoromethyl)thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  用S-（二氟甲基）盐对苯酚和硫酚进行二氟甲基化：反应，作用域和机理研究。

  摘要：

  描述了一种用于苯酚和硫酚的二氟甲基化的简便实用方法。利用最近开发的稳定的S-（二氟甲基）ulf盐作为二氟卡宾的前体，在氢氧化锂的存在下，很容易将各种不同官能化的苯酚和硫酚以良好或优异的收率转化为其相应的芳基二氟甲基醚。 。系统地研究了各种O，S-亲核试剂对二氟卡宾的化学选择性，表明反应顺序为ArS-> RS-，ArO-> ROH> RO-，ArSH，ArOH，RSH。

  DOI：

  10.1021/acs.joc.9b02424

文献信息

• Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines
  作者：Jiao Yu、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1002/anie.201710186

  日期：2017.12.22

  The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o‐phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one‐pot process

  描述了在温和条件下由二氟卡宾生成的硫代羰基氟化物与各种胺的反应。仲胺，伯胺和邻苯二胺分别转化为硫代氨基甲酰氟，异硫氰酸酯和二氟甲基硫代杂环。硫氨甲酰氟通过一锅法进一步转化为三氟甲基化胺。硫代羰基氟化物在原位生成，并在温和条件下在一锅中迅速完全转化；因此，不需要特殊的安全预防措施。
• Unusual difluoromethylation of 2-mercaptoazoles
  作者：K.I. Petko、L.M. Yagupolskii

  DOI：10.1016/s0022-1139(01)00350-5

  日期：2001.5

  The conditions for difluoromethylation of 2-mercaptobenzimidazoles with difluorocarbene (CHClF2 in alkaline medium) at the sulfur atom or at two reaction centres - sulfur and nitrogen or two nitrogen atoms - were found. In the similar reaction, 2-mercapto-4(5)-(4-nitrophenyl)imidazole gives the product of bis(difluoromethylation) at the sulfur and nitrogen atoms. Benzimidazoles with two fluorinated alkyl substituents at the two nitrogen atoms were prepared for the first time. The N-difluoromethyl derivative of benzothiazole-2-thione was obtained by this procedure. (C) 2001 Elsevier Science B.V. All rights reserved.
• Difluoromethylation of Phenols and Thiophenols with the <i>S</i>-(Difluo-romethyl)sulfonium Salt: Reaction, Scope, and Mechanistic Study
  作者：Guo-Kai Liu、Wen-Bing Qin、Xin Li、Li-Ting Lin、Henry N. C. Wong

  DOI：10.1021/acs.joc.9b02424

  日期：2019.12.20

  A facile and practical approach for the difluoromethylation of phenols and thiophenols was described. Making use of the recently developed bench-stable S-(difluoromethyl)sulfonium salt as the difluorocarbene precursor, a wide variety of diversely functionalized phenols and thiophenols were readily converted to their corresponding aryl difluoromethyl ethers in good to excellent yields in the presence

  描述了一种用于苯酚和硫酚的二氟甲基化的简便实用方法。利用最近开发的稳定的S-（二氟甲基）ulf盐作为二氟卡宾的前体，在氢氧化锂的存在下，很容易将各种不同官能化的苯酚和硫酚以良好或优异的收率转化为其相应的芳基二氟甲基醚。 。系统地研究了各种O，S-亲核试剂对二氟卡宾的化学选择性，表明反应顺序为ArS-> RS-，ArO-> ROH> RO-，ArSH，ArOH，RSH。