ethyl 1,1,3-trimethyl-2,2-dioxo-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate | 1072194-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1,1,3-trimethyl-2,2-dioxo-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate
• 英文别名: ethyl 5-(4-fluorophenyl)-1,1,3-trimethyl-2,2-dioxo-7-phenyl-3H-pyrrolo[1,2-c][1,3]thiazole-6-carboxylate
• CAS: 1072194-42-3
• 化学式: C₂₄H₂₄FNO₄S
• 分子量: 441.523
• InChiKey: DFYXHGMOCMMGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1,1,3-trimethyl-2,2-dioxo-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate 600.0 ℃ 、3.0 Pa 条件下， 以40%的产率得到ethyl 1-ethyl-2-(4-fluorophenyl)-5-isopropenyl-4-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles

  摘要：

  The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic [1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.079
• 作为产物：
  描述：

  ethyl 1,1,3-trimethyl-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以61%的产率得到ethyl 1,1,3-trimethyl-2,2-dioxo-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles

  摘要：

  The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic [1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.079