N-(6-methyl-[2]pyridyl)-N'-phenyl-hydrazine | 533935-56-7

• 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: N-(6-methyl-[2]pyridyl)-N'-phenyl-hydrazine
• 英文别名: N-(6-Methyl-[2]pyridyl)-N'-phenyl-hydrazin；1-(6-Methylpyridin-2-yl)-2-phenylhydrazine
• CAS: 533935-56-7
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: RHWMUFMOAZAUGV-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C (decomp)
• 沸点：
  327.4±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(6-methyl-[2]pyridyl)-N'-phenyl-hydrazine 在 盐酸 、 乙醇 作用下， 生成 5-(4-benzylidenamino-phenyl)-6-methyl-[2]pyridylamine
  参考文献：
  名称：

  Beyer et al., Chemische Berichte, 1958, vol. 91, p. 247,253

  摘要：

  DOI：
• 作为产物：
  描述：

  6-methyl-2-(phenylazo)pyridine 在 ammonium acetate 、 锌 作用下， 生成 N-(6-methyl-[2]pyridyl)-N'-phenyl-hydrazine
  参考文献：
  名称：

  Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a New Family of Stable Annulated N-Heterocyclic Carbenes: Synthesis, Reactivity, and Their Application in Coordination Chemistry and Organocatalysis

  摘要：

  General synthetic avenues to the pyrido-annulated triazolium salts with different steric and electronic properties have been developed. This architecture can be readily altered with different N-alkyl or aryl substituents at the N2 position of the triazole ring and modifications to the pyridine backbone. Deprotonation of the triazolium salts 12 with NaH led to formation of stable carbenes 11 at room temperature as clearly demonstrated through ESI mass spectra and by observation of the characteristic C-13 NMR resonance for the carbene carbon at delta = 202-208 ppm. In sharp contrast, treatment of these triazolium salts with K2CO3 led to dimerization of free carbenes 11. The dimeric enetetramine (11b)(2) Could react with elemental sulfur to deliver the corresponding thiourea 16 in toluene at 80 degrees C in good yield. A silver complex with the pyrido[1,2-a][1,2,4]triazol-3-ylidene is described, and the molecular structure of complex 17 was established by X-ray crystallography. The triazolium salts 12 turned out to be powerful catalysts in catalytic benzoin condensations and transesterifications at 25 degrees C. The catalytic activity was largely dependent on the steric and electronic nature of the R-1 and R-2 substituents of the triazolium salt. We rationalized that this type of triazolium-catalyzed benzoin condensations should undergo the "traditional" Breslow mechanism rather than the pathway of the dimer (11)(2) as the real catalytic species.

  DOI：

  10.1021/jo801349d

文献信息

• Tetracarbonylmolybdenum complexes of 2-(phenylhydrazino)pyridine ligands.
  作者：Martin N Ackermann、Keara B Moore、Amanda S Colligan、Jennifer A Thomas-Wohlever、Kirk J Warren

  DOI：10.1016/s0022-328x(02)02140-x

  日期：2003.2

  The 2-(phenythydrazino)pyridine (2-PHP) complexes cis-Mo(CO)(4)(X-2-(phenylhydrazino)pyridine) (X = 4-CH3O, 4-CH3, H, 4-Cl, 5-Br, 6-CH3, 4,6-(CH3)(2)) and CiS-MO(CO)(4)(2-(2-CH3-phenylhydrazino)pyridine) have been synthesized and characterized. The properties of these complexes are compared with those of the analogous 2-(phenylazo)pyridine (2-PAP) complexes. The lack of the pi-accepting azo group in the 2-PHP ligands leads to less stable complexes, including the inability even to isolate the complex with X = CF3. The 2-PHP complexes show very good correlations among the Mo-95-NMR chemical shift, the sum of the carbonyl stretching frequencies, and the Hammett sigma parameter for the pyridyl substituents. There is also an excellent correlation (r = 0.978, n = 7) of the Mo-95 chemical shift of the 2-PHP complexes with the shift for the 2-PAP complexes. The failure of the complexes with X 6-CH3 or 4,6-(CH3)(2) or the complexcis-Mo(CO)(4)(2-(2-CH3-phenylhydrazino)pyridine) to fit some of the correlations is attributed to steric or electronic effects. The 2-hydrazinopyridine complex cis-Mo(CO)(4)(H2NHNC5H4N) also was characterized. (C) 2002 Elsevier Science B.V. All rights reserved.