1-(吡啶-2-基)-2-苯基肼 | 101451-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(吡啶-2-基)-2-苯基肼
• 英文名称: 2-(phenylhydrazino)pyridine
• 英文别名: 2-(2-phenylhydrazino)pyridine；1-(pyridin-2-yl)-2-phenylhydrazine；N-phenyl-N'-[2]pyridyl-hydrazine；N-Phenyl-N'-[2]pyridyl-hydrazin；1-phenyl-2-pyridin-2-ylhydrazine
• CAS: 101451-19-8
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: XRLBRBQOCZTXSH-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: benzene (71-43-2))
• 沸点：
  317.5±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-(吡啶-2-基)-2-苯基肼 在 盐酸 、 乙醇 作用下， 生成 5-(4-benzylidenamino-phenyl)-[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：

  亚硝基苯 在 氯化铵 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(吡啶-2-基)-2-苯基肼
  参考文献：
  名称：

  使用 HBr 催化剂基于过氧化氢氧化肼

  摘要：

  偶氮化合物（RN = NR'）是一类重要的有机分子，在有机合成中有着广泛的应用。在此，我们报告了使用 5 mol% HBr 和过氧化氢作为末端氧化剂将肼 (RNH-NHR') 高效、实用且无金属氧化成偶氮化合物的方法。这种新方法已经通过 40 个示例得到了很好的证明。此外，我们展示了两个一锅序反应的例子，包括我们的肼氧化/水解/Heck 反应或铜催化的芳基硼酸 N-芳基化反应。该协议的独特优势包括无金属催化、废物预防和易于操作。

  DOI：

  10.1016/j.tet.2021.132546

文献信息

• Pyrido[1,2-<i>a</i>][1,2,4]triazol-3-ylidenes as a New Family of Stable Annulated <i>N</i>-Heterocyclic Carbenes: Synthesis, Reactivity, and Their Application in Coordination Chemistry and Organocatalysis
  作者：Yajun Ma、Siping Wei、Jingbo Lan、Jingzhi Wang、Rugang Xie、Jingsong You

  DOI：10.1021/jo801349d

  日期：2008.11.7

  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.
• 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.
• HERBICIDAL AND FUNGICIDAL COMPOSITIONS AND THEIR USES
  申请人：The Regents of the University of California

  公开号：US20170280718A1

  公开（公告）日：2017-10-05

  Described herein are compounds of Formulas I-XIII and agrochemically acceptable salts thereof having herbicidal and fungicidal activity. Also disclosed herein are herbicidal and fungicidal compositions, including compounds of Formula I-XIII or agrochemically acceptable salts thereof, and methods of controlling unwanted vegetation or fungus using compositions including the compound of Formula I-XIII or an agrochemically acceptable salt thereof.
• Hydrogen peroxide based oxidation of hydrazines using HBr catalyst
  作者：Jian Wang、Zichao Ma、Wanting Du、Liming Shao

  DOI：10.1016/j.tet.2021.132546

  日期：2021.12

  Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples

  偶氮化合物（RN = NR'）是一类重要的有机分子，在有机合成中有着广泛的应用。在此，我们报告了使用 5 mol% HBr 和过氧化氢作为末端氧化剂将肼 (RNH-NHR') 高效、实用且无金属氧化成偶氮化合物的方法。这种新方法已经通过 40 个示例得到了很好的证明。此外，我们展示了两个一锅序反应的例子，包括我们的肼氧化/水解/Heck 反应或铜催化的芳基硼酸 N-芳基化反应。该协议的独特优势包括无金属催化、废物预防和易于操作。
• Beyer et al., Chemische Berichte, 1958, vol. 91, p. 247,253
  作者：Beyer et al.

  DOI：——

  日期：——