2-[氯(二氟)甲基]-1,3-苯并噻唑 | 202396-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-[氯(二氟)甲基]-1,3-苯并噻唑
• 英文名称: 2-(difluorochloromethyl)benzothiazole
• 英文别名: 2-(chlorodifluoromethyl)benzothiazole；2-(Chlorodifluoromethyl)benzo[d]thiazole；2-[chloro(difluoro)methyl]-1,3-benzothiazole
• CAS: 202396-46-1
• 化学式: C₈H₄ClF₂NS
• 分子量: 219.642
• InChiKey: VHSLOVYELUNGOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[氯(二氟)甲基]-1,3-苯并噻唑 在 manganese(IV) oxide 、 锌 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(benzothiazol-2-yl)-2,2-difluoro-1-(2,4-difluorophenyl)ethanone
  参考文献：
  名称：

  New Antifungal 1,2,4-Triazoles with Difluoro(heteroaryl)methyl Moiety.

  摘要：

  新型1, 2, 4-三氮唑化合物（1），具有二氟(杂环基)甲基结构，通过1-芳基-2, 2-二氟-2-(杂环基)乙酮（2）的设计与合成而得，该中间体通过两种途径制备：一种是从乙基2, 2-二氟(杂环基)乙酸酯与苯基锂反应开始（途径A），另一种则是从氯二氟(杂环基)甲烷与苯甲醛反应开始（途径B）。除了化合物1g外，所有化合物1均表现出体外抗真菌活性，尤其是(+)-1f，其活性与伊曲康唑相当甚至更优。

  DOI：

  10.1248/cpb.48.982
• 作为产物：
  描述：

  2-chloro-2,2-difluoro-N-phenylethanimidoyl chloride 在 ammonium cerium (IV) nitrate 、 sodium hydrosulfide monohydrate 、 碳酸氢钠 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[氯(二氟)甲基]-1,3-苯并噻唑
  参考文献：
  名称：

  Switching reaction pathways of trifluoromethylated thiobenzanilides by choice of different oxidative systems

  摘要：

  Trifluoromethylated thiobenzanilides are efficiently converted to 2-trifluoromethylbenzothiazoles via intramolecular oxidative cyclization under CAN/NaHCO(3) oxidation, while the dimerized products with "-S-S-" bond linkage are obtained when PIDA is used as an oxidant. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.02.010

文献信息

• Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[<i>d</i>]imidazothiazoles
  作者：Jian Wang、Jing Li、Qiang Zhu

  DOI：10.1021/acs.orglett.5b02694

  日期：2015.11.6

  benzothiazoles. When the C2 position of benzothiazole is linked to a C–H or C–C bond, benzo[d]imidazo[2,1-b]thiazoles are obtained through a novel rearrangement via C–S bond cleavage and formation of a new C–S bond. When 2-chloro- or 2-bromobenzothiazoles are used under the same reaction conditions, the isomeric benzo[d]imidazo[5,1-b]thiazoles are formed selectively. These reactions proceed smoothly in moderate

  通过α-亚甲基异氰化物与苯并噻唑的铜促进的环加成反应，已开发出可调谐途径生成苯并[ d ]咪唑并噻唑的两种异构体。当苯并噻唑的C2位置与C–H或C–C键相连时，通过C–S键的裂解和新C的形成，通过新颖的重排可以获得苯并[ d ]咪唑基[2,1- b ]噻唑–S键。当在相同反应条件下使用2-氯-或2-溴苯并噻唑时，选择性地形成异构体苯并[ d ]咪唑并[5，1- b ]噻唑。这些反应在室温下以中等至极好的收率顺利进行，并且可以容忍各种官能团。
• A novel synthesis of 2-per(poly)fluoroalkyl-1H-benzimidazoles or 2-per(poly) fluoroalkyl benzothiazoles
  作者：Quan-Fu Wang、Yun-Yu Mao、Shi-Zheng Zhu、Chang-Ming Hu

  DOI：10.1016/s0022-1139(99)00012-3

  日期：1999.6

  A new method for the preparation of 2-per(poly)fluoroalkyl-1H-benzimidazoles or 2-per(poly)fluoroalkyl benzothiazoles from reaction of readily available alpha-per(poly)fluoroalkyl aldehydes with o-phenylenediamine or 2-aminobenzenethiol is presented. A possible reaction pathway is suggested. (C) 1999 Elsevier Science S.A. All rights reserved.
• A General and Straightforward Method for the Synthesis of 2-Trifluoromethylbenzothiazoles
  作者：Jiangtao Zhu、Zixian Chen、Haibo Xie、Shan Li、Yongming Wu

  DOI：10.1021/ol1006899

  日期：2010.5.21

  An efficient one-pot method for the synthesis of 2-trifluoromethylbenzothiazoles by the treatment of trifluoromethylimidoyl chlorides with sodium hydrosulfide hydrate using PdCl(2) as the sole catalyst in DMSO is described. The reaction proceeds via thiolation/C H bond functionalization/C S bond formation in moderate to high yields with good functional group tolerance.
• Benzothiazol-2-yl(difluoro)methanesulfonic acid: Synthesis and reactions
  作者：V. P. Nazaretyan、N. D. Volkov、N. I. Liptuga

  DOI：10.1134/s1070428006080148

  日期：2006.8

  The condensation of o-aminothiophenol with sulfodifluoroacetic acid led to the formation of benzothiazol-2-yl(difluoro)methanesulfonic acid whose aryldiazonium salts were converted by pyrolysis into aryl benzothiazol-2-yl(difluoro)methanesulfonates.
• New Antifungal 1,2,4-Triazoles with Difluoro(heteroaryl)methyl Moiety.
  作者：Hiromichi ETO、Yasushi KANEKO、Takao SAKAMOTO

  DOI：10.1248/cpb.48.982

  日期：——

  New 1, 2, 4-triazoles (1) having a difluoro(heteroaryl)methyl moiety were designed and synthesized via 1-aryl-2, 2-difluoro-2-(heteroaryl)ethanones (2), which were prepared by two routes starting from the reaction of ethyl 2, 2-difluoro(heteroaryl)acetate with phenyllithiums (Route A) and from the reaction of chlorodifluoro(heteroaryl)methane with benzaldehydes (Route B). The compounds 1 except for 1g show antifungal activities against yeasts and filamentous fungi in vitro, especially (+)-1f have equal or superior activities compared to those of itraconazole.

  新型1, 2, 4-三氮唑化合物（1），具有二氟(杂环基)甲基结构，通过1-芳基-2, 2-二氟-2-(杂环基)乙酮（2）的设计与合成而得，该中间体通过两种途径制备：一种是从乙基2, 2-二氟(杂环基)乙酸酯与苯基锂反应开始（途径A），另一种则是从氯二氟(杂环基)甲烷与苯甲醛反应开始（途径B）。除了化合物1g外，所有化合物1均表现出体外抗真菌活性，尤其是(+)-1f，其活性与伊曲康唑相当甚至更优。