N-[1-(1H-pyrrol-2-yl)ethylidene]aniline | 91677-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
• 英文别名: 2-{1-[(phenyl)imino]ethyl}pyrrole；N-phenyl-1-(1H-pyrrol-2-yl)ethan-1-imine；[[1-(1H-pyrrole-2-yl)ethylidene]amino]benzene；NC4H4C(Me)NC6H5；N-[1-(2H-Pyrrol-2-ylidene)ethyl]aniline；N-phenyl-1-(1H-pyrrol-2-yl)ethanimine
• CAS: 91677-16-6
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: OHDSFKNULDOUJM-UHFFFAOYSA-N

物化性质

• 熔点：
  132.10-133.70 °C(Solv: ethanol (64-17-5))
• 沸点：
  314.4±24.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[1-(1H-pyrrol-2-yl)ethylidene]aniline 、 cobalt(II) chloride 在 NaH 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到[bis(((1-(1H-pyrrole-2-yl)ethylidene)amino)benzenato)-cobalt]
  参考文献：
  名称：

  钴（II）的四面体和方形平面双（亚氨基吡咯烷基）配合物的合成与表征。

  摘要：

  一系列具有增加的体积的2-亚氨基吡咯配体前体[HNC4H3C（R）= N-2,6-R'2C6H3]（R = R'= H，1a; R = Me，R'= H，1b; R =合成H，R'= Me，1c; R = R'= Me，1d; R = H，R'= iPr，1e; R = Me，R'= iPr，1f）并用NaH去质子化，得到相应的亚氨基吡咯烷基钠盐2a-f。一组[Co（kappa2N，N'-NC4H3C（R）= N-2,6-R'2C6H3）2]类型的均化双配体Co（II）配合物（R = R'= H，3a; R = Me，R'= H，3b; R = H，R'= Me，3c; R = R'= Me，3d; R = H，R'= iPr，3e; R = Me，R'= iPr ，3f）通过使CoCl 2与相应的亚氨基吡咯烷基钠盐2a-f反应来制备。通过元素分析，磁化率测量，粉末和溶液，UV / vis

  DOI：

  10.1021/ic062125w
• 作为产物：
  描述：

  2-乙酰基吡咯 、 苯胺 在 溶剂黄146 作用下， 生成 N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
  参考文献：
  名称：

  Bis{2-[(phenylimino)ethyl]-1H-pyrrol-1-ido-κ²N,N′}nickel(II): a supramolecular structure formed by C—H...π hydrogen bonds

  摘要：

  在标题化合物[Ni(C12H11N2)2]中，NiII阳离子位于一个反转中心，具有正方形平面配位几何。这种过渡金属配合物由两个去质子化的 N,N′-二价 2-[（苯基亚氨基）乙基]-1H-吡咯-1-ide 配体围绕着一个中心 NiIIcation 组成，吡咯烷环和亚胺基团相互平行。Ni-N 键长度为 1.894 (3) 至 1.939 (2) Å，咬合角为 83.13 (11)°。Ni-N（吡咯烷）键比 Ni-N（亚氨基）键短得多。苯基环的平面与 NiN4 的中心平面成 78.79 (9)° 的二面角。分子间的 C-H...π 相互作用将这些分子连接成简单的链，其中苯基 β-C 原子是供体。分子内也存在 C-H...π 相互作用。

  DOI：

  10.1107/s0108270113018118

文献信息

• Efficient Microwave-Assisted Syntheses of A Series of Novel Mono(imino)pyrrolyl Compounds
  作者：Biyun Su、Xiaoteng Li、Xudong Wang、Qianding Li

  DOI：10.3987/com-15-13265

  日期：——

  A series of novel mono(imino)pyrroles that were hard to prepare under traditional solvent reaction condition were readily synthesized under solvent free condition using microwave chemistry via p-TSA (p-toluenesulfonic acid) catalyzed Schiff base condensation. The structures of the compounds were characterized by means of MS, H-1 NMR, IR, elementary analysis and X-ray diffraction analysis. The reactivity of different aromatic amines with 2-acetylpyrrole was discussed.
• Vats, J. L.; Sharma, S.; Gupta, N. C., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1984, vol. 14, p. 521 - 536
  作者：Vats, J. L.、Sharma, S.、Gupta, N. C.、Singh, H.

  DOI：——

  日期：——
• Octahedral Co(III) complexes of 2-(phenylimino)pyrrolyl ligands: Synthesis and structural characterisation
  作者：Clara S.B. Gomes、Sónia A. Carabineiro、Pedro T. Gomes、M. Teresa Duarte、M. Amélia N.D.A. Lemos

  DOI：10.1016/j.ica.2010.12.032

  日期：2011.2

  The reactions of CoCl2 with three equivalents of 2-(phenylimino)pyrrolyl sodium salts, performed under a nitrogen atmosphere, lead to the formation of the Co(III) complexes [Co(kappa N-2,N'-NC4H3C(H)=N-C6H5)(3)] (2a), [Co(kappa N-2,N'-NC4H3C(CH3)=N-C6H5)(3)] (2b) and [Co(kappa N-2,N'-NC16H9C(H)=N-C6H5)(3)] (2c), accommodating three chelating iminopyrrolyl ligands. Complexes 2a-c were obtained in moderate yields, and their characterisation by H-1, C-13 NMR and X-ray diffraction show they are diamagnetic and have an octahedral geometry about the cobalt centre, respectively. Uncharacterised products were obtained in the same reaction involving ligand precursors such as 2-(2,6-dimethylphenylimino) pyrrolyl sodium salts, which is attributed to a greater steric hindrance in the coordination of three of these bulkier ligands. The redox behaviour of complexes 2a-c shows an irreversible reduction wave with a peak potential in the range -3.2 to -3.7 V. Upon reduction, the complexes decompose giving rise, in the case of 2a, to a redox pattern compatible with the formation of [Co(kappa N-2,N'-NC4H3C(H)=N-C6H5)(2)]. (C) 2010 Elsevier B.V. All rights reserved.