3-methyl-7-(2-phenyl-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide | 139313-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-7-(2-phenyl-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide
• 英文别名: 3-Methyl-7-(2-oxo-2-phenylethyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazol-7-ium bromide；2-(3-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-4-ium-7-yl)-1-phenylethanone;bromide
• CAS: 139313-11-4
• 化学式: Br*C₁₄H₁₅N₂OS
• 分子量: 339.256
• InChiKey: CCLDCCIAQTZFMK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-7-(2-phenyl-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide 、 丙炔酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 ethyl (2Z,5Z)-6-<5-benzoyl-2,3-dihydro-7-(ethoxycarbonyl)-1H-pyrrolo<1,2-a>imidazol-1-yl>-4-thiahepta-2,5-dienoate 、 ethyl (2E,5Z)-6-<5-benzoyl-2,3-dihydro-7-(ethoxycarbonyl)-1H-pyrrolo<1,2-a>imidazol-1-yl>-4-thiahepta-2,5-dienoate
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of 5,6-dihydroimidazo[2,1-b]thiazolium betaines

  摘要：

  5,6-Dihydroimidazo[2,1-b]thiazolium betaines were generated in situ from 3,7-disubstituted 5,6-dihydroimidazo[2,1-b]thiazolium bromides and triethylamine. The reaction of these imidazothiazolium betaines with acetylenic dipolarophiles, such as ethyl propiolate, dimethyl acetylenedicarboxylate, and dibenzoylacetylene, provided geometric cis,trans isomers containing 2,3-dihydro-1H-pyrrolo[1,2-a]imidazole. We have proposed a mechanism of this reaction that involves 1,3-dipolar cycloaddition, isomeric rearrangement, and then nucleophilic addition successively. The ratio of trans and cis isomers depended on the temperature and solvents. The stereoselectivity of trans isomers increased with increasing temperature and decreasing polarity of solvents.

  DOI：

  10.1021/jo00034a029
• 作为产物：
  描述：

  3-methyl-5,6-dihydroimidazo<2,1-b>thiazole 、 2-溴苯乙酮 以 丙酮 为溶剂， 反应 5.0h， 以87%的产率得到3-methyl-7-(2-phenyl-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of 5,6-dihydroimidazo[2,1-b]thiazolium betaines

  摘要：

  5,6-Dihydroimidazo[2,1-b]thiazolium betaines were generated in situ from 3,7-disubstituted 5,6-dihydroimidazo[2,1-b]thiazolium bromides and triethylamine. The reaction of these imidazothiazolium betaines with acetylenic dipolarophiles, such as ethyl propiolate, dimethyl acetylenedicarboxylate, and dibenzoylacetylene, provided geometric cis,trans isomers containing 2,3-dihydro-1H-pyrrolo[1,2-a]imidazole. We have proposed a mechanism of this reaction that involves 1,3-dipolar cycloaddition, isomeric rearrangement, and then nucleophilic addition successively. The ratio of trans and cis isomers depended on the temperature and solvents. The stereoselectivity of trans isomers increased with increasing temperature and decreasing polarity of solvents.

  DOI：

  10.1021/jo00034a029