6-(3-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole | 92754-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(3-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
• 英文别名: 6-(3-Methoxyphenyl)-3-methylimidazo[2,1-b][1,3]thiazole
• CAS: 92754-13-7
• 化学式: C₁₃H₁₂N₂OS
• mdl: MFCD08815582
• 分子量: 244.317
• InChiKey: LIDPBKZLRKODSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole 在 盐酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 8-Hydroxy-8-(3-methoxy-phenyl)-5-methyl-8H-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3-one
  参考文献：
  名称：

  Ring-ring interconversions. Part 2. Effect of the substituent on the rearrangement of 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles into 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-ones. A novel class of potential antitumor agents

  摘要：

  The reaction of several 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles with hydrochloric acid by refluxing in ethanol gives new 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c] [1,2,4]oxadiazol-3-ones for testing of their biological activity. By carrying out the reaction at room temperature it has been possible to isolate reaction intermediates to which structures have been assigned. This study has provided information on the reaction mechanism and on the effect of the substituent in the phenyl ring on the yield of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00189-1
• 作为产物：
  描述：

  2-溴-3‘-甲氧基苯乙酮 在 氢溴酸 作用下， 以 丙酮 为溶剂， 反应 1.17h， 生成 6-(3-Methoxy-phenyl)-3-methyl-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Andreani; Rambaldi; Bonazzi, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 219 - 222

  摘要：

  DOI：

文献信息

• Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine
  作者：Haibo Mei、Chen Xie、Lingmin Wu、Vadim A. Soloshonok、Jianlin Han、Yi Pan

  DOI：10.1039/c3ob41785a

  日期：——

  reasonably good yields (55%–79%) and exceptionally high stereoselectivity (>99 : 1 dr). This method presents a general approach for the preparation of a new type of biologically relevant compounds containing pharmacophoric imidazo[2,1-b]thiazole and (trifluoro)ethylamine groups.

  咪唑并[2,1-的不对称曼尼希反应b ]噻唑衍生的亲核试剂与（S小号） - N-叔-butanesulfinyl（3,3,3-）-trifluoroacetaldimine发现具有相当好的产率继续进行（55％-79％ ）和极高的立体选择性（> 99：1 dr）。该方法为制备含有药效基咪唑并[2，1- b ]噻唑和（三氟）乙胺基团的新型生物相关化合物提供了一种通用方法。
• ANDREANI, A.;RAMBALDI, M.;BONAZZI, D.;LELLI, G.;BOSSA, R.;GALATULAS, I., EUR. J. MED. CHEM., 1984, 19, N 3, 219-222
  作者：ANDREANI, A.、RAMBALDI, M.、BONAZZI, D.、LELLI, G.、BOSSA, R.、GALATULAS, I.

  DOI：——

  日期：——
• Andreani; Rambaldi; Bonazzi, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 219 - 222
  作者：Andreani、Rambaldi、Bonazzi、et al.

  DOI：——

  日期：——
• Ring-ring interconversions. Part 2. Effect of the substituent on the rearrangement of 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles into 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-ones. A novel class of potential antitumor agents
  作者：Roberta Billi、Barbara Cosimelli、Domenico Spinelli、Mirella Rambaldi

  DOI：10.1016/s0040-4020(99)00189-1

  日期：1999.4

  The reaction of several 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles with hydrochloric acid by refluxing in ethanol gives new 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c] [1,2,4]oxadiazol-3-ones for testing of their biological activity. By carrying out the reaction at room temperature it has been possible to isolate reaction intermediates to which structures have been assigned. This study has provided information on the reaction mechanism and on the effect of the substituent in the phenyl ring on the yield of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.