N'-[(E)-3-oxo-3-(2-thienyl)-1-(trifluoromethyl)propylidene]pyridine-3-carbohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N'-[(E)-3-oxo-3-(2-thienyl)-1-(trifluoromethyl)propylidene]pyridine-3-carbohydrazide
• 英文别名: N'-[(2E)-1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)butan-2-ylidene]pyridine-3-carbohydrazide；N-[(E)-(1,1,1-trifluoro-4-oxo-4-thiophen-2-ylbutan-2-ylidene)amino]pyridine-3-carboxamide
• 化学式: C₁₄H₁₀F₃N₃O₂S
• 分子量: 341.314
• InChiKey: BBZOPDDWLKIKKE-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-吡啶甲酰肼 、 2-噻吩甲酰三氟丙酮 以 甲醇 为溶剂， 以79%的产率得到N'-[(E)-3-oxo-3-(2-thienyl)-1-(trifluoromethyl)propylidene]pyridine-3-carbohydrazide
  参考文献：
  名称：

  Reaction of aroyl- and hetaroyltrifluoroacetones with acylhydrazines: Regioselectivity and tautomerism of the condensation products

  摘要：

  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.

  DOI：

  10.1134/s107036320710012x

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.