1,1,1-trifluoro-3-(phenyl-hydrazono)-pentane-2,4-dione

• 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: 1,1,1-trifluoro-3-(phenyl-hydrazono)-pentane-2,4-dione
• 英文别名: (3E)-1,1,1-trifluoro-3-(phenylhydrazinylidene)pentane-2,4-dione
• 化学式: C₁₁H₉F₃N₂O₂
• 分子量: 258.2
• InChiKey: UBVSZQCHQCPPEJ-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-3-(phenyl-hydrazono)-pentane-2,4-dione 、 甲胺 以 乙醇 为溶剂， 反应 0.33h， 以74%的产率得到(Z)-4-(N-methyl)amino-1,1,1-trifluoro-3-phenylazopent-3-en-2-one
  参考文献：
  名称：

  The transformations of fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds with methylamine

  摘要：

  Fluoroalkylated 1,2,3-triketone 2-arylhydrazones and 2-arylhydrazono-3-oxo esters react variously with methylamine depending on the structure of the fluorinated substituent. 2-Arylhydrazono-1,3-dicarbonyl compounds having "short" fluoroalkyl substituents condense with methylamine at the carbonyl group attached to the non-fluorinated substituent whereas ones containing a lengthy polyfluoroalkyl substituent undergo haloformic cleavage as a result of the amine addition at the carbonyl group bearing such a substituent. The resulting 2-arylazo-3-(N-methyl)amino- 1-polyfluoroket-2-en-1-ones and 1-(N-methyl)amino-2-arylhydrazono-3-fluoroalkyl-3-oxopropanamides have complexing properties, and they can bind to nickel(II) and copper(11) ions. Nickel chelates can be obtained by a three-component condensation of 2-arylhydrazono-1,3-dicarbonyl compounds and methylamine in the presence of nickel(II) cations. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.009

文献信息

• Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines
  作者：E. V. Shchegol’kov、Ya. V. Burgart、O. G. Khudina、V. I. Saloutin、O. N. Chupakhin

  DOI：10.1007/s11172-005-0158-y

  日期：2004.11

  Fluoroalkyl-containing 1,2,3-triketone 2-(2,3-dimethyl-5-oxo-1-phenyl-1,2-dihydropyrazol-4-yl)-, 2-(4-ethoxycarbonylpyrazol-3-yl)-, and 2-(1,2,4-triazol-3-yl)hydrazones were synthesized by the azo coupling reactions of fluorinated 1,3-diketones with the corresponding hetaryldiazonium chlorides. The hetarylhydrazones thus synthesized were subjected to cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to give 3-fluoroalkyl-4-hetarylazopyrazoles.

  含氟烷基的1,2,3-三酮2-(2,3-二甲基-5-氧代-1-苯基-1,2-二氢吡唑-4-基)-,2-(4-乙氧基羰基吡唑-3-基)通过氟化1,3-二酮与相应的杂芳基重氮氯化物的偶氮偶联反应合成了-、和2-(1,2,4-三唑-3-基)腙。将由此合成的杂芳基腙与肼在1，3-二羰基片段处进行环化缩合，得到3-氟烷基-4-杂芳基偶氮吡唑。
• Condensation of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones with methylamine
  作者：E. V. Shchegol’kov、Ya. V. Burgart、P. A. Slepukhin、O. N. Kazheva、G. V. Shilov、O. A. D’yachenko、V. I. Saloutin

  DOI：10.1134/s1070428007120081

  日期：2007.12

  Fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones react with methylamine in different ways, depending on the substrate structure. Arylhydrazones having a short fluoroalkyl substituent (R-F = CF3, HCF2CF2) react at the carbonyl group adjacent to the nonfluorinated substituent to give 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1-ones. Arylhydrazones with a long-chain fluoroalkyl group (RF = C3F7 and longer) and a bulky nonfluorinated group take up methylamine molecule at the carbonyl group linked to the fluorinated substituent, and the subsequent haloform reaction yields N-methyl-2-arylhydrazono-3-oxobutanamides. Both types of products are formed in reactions of methylamine with 1,2,3-triketone 2-arylhydrazones having a long fluoroalkyl group and methyl group at the other carbonyl group. L Template condensation of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones with methylamine over Ni(II) template gives bis[3-alkyl(aryl)-1-polyfluoroalkyl-3-methylamino-2-aryldiazenylprop-2-en-1-onato-N,N']nickel(II), regardless of the size of the fluoroalkyl substituent. The same complexes and their copper analogs can be obtained by treatment of 3-alkyl(aryl)-2-aryldiazenyl-3-methylamino-1-polyfluoroalkylprop-2-en-1-ones with the corresponding metal salts.