5-Hydroxy-3-(thien-2-yl)-5-trifluoromethyl-4,5-dihydropyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-Hydroxy-3-(thien-2-yl)-5-trifluoromethyl-4,5-dihydropyrazole
• 英文别名: 5-hydroxy-3-(2-thenoyl)-5-trifluoromethylpyrazoline；3-(thiophen-2-yl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-ol；3-thiophen-2-yl-5-(trifluoromethyl)-1,4-dihydropyrazol-5-ol
• 化学式: C₈H₇F₃N₂OS
• 分子量: 236.218
• InChiKey: AHLFKLUTEMOYPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-3-(thien-2-yl)-5-trifluoromethyl-4,5-dihydropyrazole 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以88%的产率得到5-(2-噻吩基)-3-(三氟甲基)-1H-吡唑
  参考文献：
  名称：

  Formation and dehydration of a series of 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles

  摘要：

  Reaction of five (3-oxo-4,4,4-trifluorobutanoyl)heterocycles with hydrazine hydrate under mild conditions gave the corresponding 3-heterocyclyl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles. Thermal elimination of water from the 3-(thien-2-yl), 3-(pyridin-2-yl) and 3-(pyridin-4-yl) compounds readily gave the corresponding pyrazoles but acid catalysis was required to form 3-(benzothiazol-2-yl)-5-trifluoromethylpyrazole and 3-(1-methylbenzimidazol-2-yl)-5-trifluoromethylpyrazole. More forcing conditions were required for the analogous dehydration/aromatisations giving 3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole and 3,5-bis(trifluoromethyl)-1-pentafluorophenylpyrazole. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00011-1
• 作为产物：
  描述：

  2-噻吩甲酰三氟丙酮 在 一水合肼 作用下， 以 乙醚 为溶剂， 以68%的产率得到5-Hydroxy-3-(thien-2-yl)-5-trifluoromethyl-4,5-dihydropyrazole
  参考文献：
  名称：

  1,1,1-Trifluoro-3-(2-thenoyl)acetone in Reactions with Hydrazines

  摘要：

  Properties of 1,1,1-trifluoro-3-(2-thenoyl)acetone and its reactions with hydrazine hydrate, 2,4-dinitrophenylhydrazine, and 1,1-dimethylhydrazone are studied.

  DOI：

  10.1023/b:rugc.0000016035.61500.d1

文献信息

• Formation and dehydration of a series of 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles
  作者：Shiv P Singh、Dalip Kumar、Brian G Jones、Michael D Threadgill

  DOI：10.1016/s0022-1139(99)00011-1

  日期：1999.4

  Reaction of five (3-oxo-4,4,4-trifluorobutanoyl)heterocycles with hydrazine hydrate under mild conditions gave the corresponding 3-heterocyclyl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles. Thermal elimination of water from the 3-(thien-2-yl), 3-(pyridin-2-yl) and 3-(pyridin-4-yl) compounds readily gave the corresponding pyrazoles but acid catalysis was required to form 3-(benzothiazol-2-yl)-5-trifluoromethylpyrazole and 3-(1-methylbenzimidazol-2-yl)-5-trifluoromethylpyrazole. More forcing conditions were required for the analogous dehydration/aromatisations giving 3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole and 3,5-bis(trifluoromethyl)-1-pentafluorophenylpyrazole. (C) 1999 Elsevier Science S.A. All rights reserved.
• 1,1,1-Trifluoro-3-(2-thenoyl)acetone in Reactions with Hydrazines
  作者：K. A. Volkova、A. N. Volkov、A. I. Albanov、A. S. Nakhmanovich、V. A. Lopyrev

  DOI：10.1023/b:rugc.0000016035.61500.d1

  日期：2003.10

  Properties of 1,1,1-trifluoro-3-(2-thenoyl)acetone and its reactions with hydrazine hydrate, 2,4-dinitrophenylhydrazine, and 1,1-dimethylhydrazone are studied.