2-(5-hydroxy-3-(2-thienyl)-5-trifluoromethylpyrazolin-1-yl)-4-(4-chlorophenyl)thiazole | 476172-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-hydroxy-3-(2-thienyl)-5-trifluoromethylpyrazolin-1-yl)-4-(4-chlorophenyl)thiazole
• 英文别名: 1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-(thiophen-2-yl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-ol；2-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-5-thiophen-2-yl-3-(trifluoromethyl)-4H-pyrazol-3-ol
• CAS: 476172-19-7
• 化学式: C₁₇H₁₁ClF₃N₃OS₂
• 分子量: 429.874
• InChiKey: QGEUNSLTLVSASJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(5-hydroxy-3-(2-thienyl)-5-trifluoromethylpyrazolin-1-yl)-4-(4-chlorophenyl)thiazole 在 乙酸酐 作用下， 反应 3.0h， 以87%的产率得到2-(3-(2-thienyl)-5-trifluoromethylpyrazol-1-yl)-4-(4-chlorophenyl)thiazole
  参考文献：
  名称：

  The regioselectivity of the formation of 2-pyrazolylthiazoles and their precursors from the reaction of 2-hydrazinothiazoles with 4,4,4-trifluoro-1-hetaryl-1,3-butanediones

  摘要：

  Reaction of 2-hydrazinothiazoles 1 with 1-thienyl- and 1-furyl-1,3-butanediones 2a,b in methanol in the presence of hydrochloric acid mainly leads to a mixture of pyrazoles 3 and pyrazolines 4 or pyrazoles 3 and 5 in strong acidic conditions. Isomeric hydrazones 6 and pyrazolines 4 were formed and isolated in these reactions in the absence of hydrochloric acid. It has been shown that the regioselectivity in the reaction of diketones 2 with hydrazine 1 is governed by both the concentration of acid and the nature of substituents in the 1,3-diketones 2. Cyclization of hydrazones 6 is shown to occur under milder conditions than dehydration for pyrazolines 4. The new heterocyclic compounds were prepared and fully characterized by NMR spectra and by X-ray analysis for 3c. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00060-x
• 作为产物：
  描述：

  4-(4-氯苯基)-2-肼基-1,3-噻唑 、 2-噻吩甲酰三氟丙酮 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以61%的产率得到2-<3-trifluoromethyl-5-(2-thienyl)pyrazol-1-yl>-4-p-chlorophenylthiazole
  参考文献：
  名称：

  The regioselectivity of the formation of 2-pyrazolylthiazoles and their precursors from the reaction of 2-hydrazinothiazoles with 4,4,4-trifluoro-1-hetaryl-1,3-butanediones

  摘要：

  Reaction of 2-hydrazinothiazoles 1 with 1-thienyl- and 1-furyl-1,3-butanediones 2a,b in methanol in the presence of hydrochloric acid mainly leads to a mixture of pyrazoles 3 and pyrazolines 4 or pyrazoles 3 and 5 in strong acidic conditions. Isomeric hydrazones 6 and pyrazolines 4 were formed and isolated in these reactions in the absence of hydrochloric acid. It has been shown that the regioselectivity in the reaction of diketones 2 with hydrazine 1 is governed by both the concentration of acid and the nature of substituents in the 1,3-diketones 2. Cyclization of hydrazones 6 is shown to occur under milder conditions than dehydration for pyrazolines 4. The new heterocyclic compounds were prepared and fully characterized by NMR spectra and by X-ray analysis for 3c. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00060-x