2-(3-nitrophenyl)benzo[d]imidazo[2,1-b]thiazole | 79889-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-nitrophenyl)benzo[d]imidazo[2,1-b]thiazole
• 英文别名: 2-(m-Nitrophenyl)imidazo[2,1-b]benzothiazole；2-(3-Nitrophenyl)imidazo[2,1-b][1,3]benzothiazole
• CAS: 79889-59-1
• 化学式: C₁₅H₉N₃O₂S
• 分子量: 295.321
• InChiKey: WUTCLFXGLBVBRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴氟甲基膦酸二乙酯 、 2-(3-nitrophenyl)benzo[d]imidazo[2,1-b]thiazole 在 rose bengal 、 碳酸氢钠 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以70%的产率得到diethyl (difluoro(2-(3-nitrophenyl)benzo[d]imidazo[2,1-b]thiazol-3-yl)methyl)phosphonate
  参考文献：
  名称：

  Organophotoredox-Catalyzed C(sp²)–H Difluoromethylenephosphonation of Imidazoheterocycles

  摘要：

  A mild and efficient method for the direct difluoromethylenephosphonation of imidazopyridines has been developed using rose bengal (RB) as a photoredox catalyst. Bis(pinacolato)diboron (B(2)pin(2)) is found to be a crucial additive in the present reaction. The present methodology is also applicable to other heterocycles like imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, and indole. The reaction possibly proceeds through a single electron transfer (SET) process.

  DOI：

  10.1021/acs.orglett.9b01954
• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 以 乙二醇甲醚 、 丁酮 为溶剂， 反应 3.0h， 生成 2-(3-nitrophenyl)benzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Imidazo[2,1-b]benzothiazoles. 2. New immunosuppressive agents

  摘要：

  A series of 2-phenylimidazo[2,1-b]benzothiazole derivatives was prepared and tested for immunological activities. Some of the compounds showed significant suppressive activity of delayed type hypersensitivity (DTH) without inhibition of humoral immunity in mice by oral administration. The most active compound was 2-(m-hydroxyphenyl)imidazo[2,1-b]benzothiazole (20).

  DOI：

  10.1021/jm00153a014

文献信息

• FeCl₃/ZnI₂-Catalyzed Synthesis of Benzo[<i>d</i>]imidazo[2,1-<i>b</i>]thiazole through Aerobic Oxidative Cyclization between 2-Aminobenzothiazole and Ketone
  作者：Subhajit Mishra、Kamarul Monir、Shubhanjan Mitra、Alakananda Hajra

  DOI：10.1021/ol5028893

  日期：2014.12.5

  The FeCl3/ZnI2-catalyzed aerobic oxidative cyclization between 2-aminobenzothiazole and ketone/chalcone for the synthesis of benzo[d]imidazo[2,1-b]thiazole is described. A variety of fused benzoimidazothiazole derivatives are obtained by this protocol.
• MASE, TOSHIYASU;ARIMA, HIDEKI;TOMIOKA, KENICHI;YAMADA, TOSHIMITSU;MURASE,+, J. MED. CHEM., 1986, 29, N 3, 386-394
  作者：MASE, TOSHIYASU、ARIMA, HIDEKI、TOMIOKA, KENICHI、YAMADA, TOSHIMITSU、MURASE,+

  DOI：——

  日期：——
• US4497817A
  申请人：——

  公开号：US4497817A

  公开（公告）日：1985-02-05