1-benzoyl-5-hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyl-5-hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole
• 英文别名: 1-benzoyl-3-methyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-ol；[5-hydroxy-3-methyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](phenyl)methanone；[5-hydroxy-3-methyl-5-(trifluoromethyl)-4H-pyrazol-1-yl]-phenylmethanone
• 化学式: C₁₂H₁₁F₃N₂O₂
• 分子量: 272.227
• InChiKey: QHRPJDWDUJXQRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  nickel(II) acetate tetrahydrate 、 三苯基膦 、 1-benzoyl-5-hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole 以 甲醇 为溶剂， 反应 24.0h， 以59%的产率得到
  参考文献：
  名称：

  Exploring the reactivity of nickel complexes in hydrodecyanation reactions

  摘要：

  In the present study, the nickel-catalyzed hydrodecyanation of organic cyanides with lithium borohydride as a cheap hydride source has been examined in detail. As precatalysts straightforward nickel complexes modified by tridentate O,N,O'-ligands and triphenylphosphane as co-ligand have been applied. Noteworthy, excellent yields and chemoselectivities were feasible for a variety of organic cyanides at low catalyst loadings and low temperature (70 degrees C) within short reaction time (3 h). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.07.068
• 作为产物：
  描述：

  三氟乙酰丙酮 、 苯甲酰肼 以 甲醇 为溶剂， 反应 24.0h， 以72%的产率得到1-benzoyl-5-hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Yakimovich; Zerova; Zelenin, Russian Journal of Organic Chemistry, 1997, vol. 33, # 3, p. 370 - 374

  摘要：

  DOI：

文献信息

• Reaction of aroyl- and hetaroyltrifluoroacetones with acylhydrazines: Regioselectivity and tautomerism of the condensation products
  作者：V. V. Pakal’nis、I. V. Zerova、S. I. Yakimovich

  DOI：10.1134/s107036320710012x

  日期：2007.10

  Acylhydrazines react with 1,3-diketones of the general formula CF3COCH2COR (where R is an aryl or hetaryl group) at both carbonyl groups. The reaction at the trifluoroacetyl group is favored by donor substituents in the aromatic ring of the 1,3-diketone or by the 2-furyl and, especially, 2-thienyl group as a hetaryl substituent, as well as by elevated temperature. The condensation products at the carbonyl group contiguous to the aryl or hetaryl ring have the structure of 5-hydroxy-4,5-dihydropyrazoles and do not undergo tautomeric transformations in solution. The condensation products at the trifluoroacetyl group have either 5-hydroxy-4,5-dihydropyrazole or hydrazone structure and give rise to ring-chain tautomeric equilibrium in solution. Electron-withdrawing substituents in the aromatic ring of the 1,3- dicarbonyl fragment and CDCl3 as solvent favor formation of the cyclic tautomer. The state of the tautomeric equilibrium is weakly sensitive to structural variations in the hydrazine component.
• Interactions of aroyl-and heteroaroyltrifluoroacetones with thiobenzoylhydrazine
  作者：V. V. Pakalnis、I. V. Zerova、S. I. Yakimovitch、V. V. Alekseyev

  DOI：10.1007/s10593-008-0081-x

  日期：2008.5

  The interaction of aroyl( heteroaroyl) trifluoroacetones with thiobenzoylhydrazine may occur at both carbonyl groups. Reaction at the trifluoroacetyl group is facilitated by terminal substituents in the 1,3-dicarbonyl part, which leads can effectively conjugate with the adjacent carbonyl group. The products of condensation at the trifluoroacetyl group are 2-[2-aryl(heteroaroyl)-2-oxoethyl]-5-phenyl-2-trifluoromethyl-2,3-dihydro-1,3,4-thiadiazoles, while condensation at the aroyl(heteroaroyl) group gave 3-aryl(heteroaryl)-5-hydroxy-1-thiobenzoyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles, which are not prone to tautomeric transformations in solution.