cis-2,4,5-tri(3-nitrophenyl)-2-imidazoline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-2,4,5-tri(3-nitrophenyl)-2-imidazoline
• 英文别名: cis-2,4,5-tris(3-nitrophenyl)-2-imidazoline；cis-2,4,5-tris(m-nitrophenyl)imidazoline；(+/-)-2,4r,5c-tris-(3-nitro-phenyl)-4,5-dihydro-1H-imidazole；(+/-)-2,4r,5c-Tris-(3-nitro-phenyl)-4,5-dihydro-1H-imidazol；(4R,5S)-2,4,5-tris(3-nitrophenyl)-4,5-dihydro-1H-imidazole
• 化学式: C₂₁H₁₅N₅O₆
• 分子量: 433.38
• InChiKey: FBMSEYNEDREPIQ-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-2,4,5-tri(3-nitrophenyl)-2-imidazoline 在 sodium hydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 7.5h， 生成 threo-N-(3-nitrobenzoyl)-N'-(3-nitrophenyl)methylidene-1,2-diamino-1,2-di(3-nitrophenyl)ethane
  参考文献：
  名称：

  Stereoselective synthesis of 1,2-diamino-1,2-diarylethane derivatives

  摘要：

  开发了一种选择性打开 cis-2,4,5-三芳基咪唑啉环的方法，以形成 erythro-1,2-二氨基-1,2-二芳基乙烷衍生物。这些开环产物，即 erythro-乙二胺衍生物，可以在 DMSO 中在强碱的存在下发生定量异构化，生成 threo-乙二胺衍生物。

  DOI：

  10.1007/s11172-005-0238-z
• 作为产物：
  描述：

  间硝基苯甲醛 在 乙酸铵 、 aluminum oxide 作用下， 反应 0.03h， 以75%的产率得到cis-2,4,5-tri(3-nitrophenyl)-2-imidazoline
  参考文献：
  名称：

  Alumina-Ammonium Acetate as an Efficient Reagent for the One-Pot Synthesis of cis-2,4,5-Triarylimidazolines from Aromatic Aldehydes

  摘要：

  A simple, efficient, and new method has been developed for the synthesis of 2,4,5-triarylimidazolines from aldehydes through a one-pot reaction of aldehydes in the presence of alumina-ammonium acetate under solvent-free conditions using microwave irradiation. This method is easy, rapid, one-pot and good to high-yielding reaction for the synthesis of 2,4,5-triarylimidazolines.

  DOI：

  10.3987/com-04-10203

文献信息

• ——
  作者：N. A. Lozinskaya

  DOI：10.1023/a:1023915024572

  日期：——

  Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.
• Alumina-Ammonium Acetate as an Efficient Reagent for the One-Pot Synthesis of cis-2,4,5-Triarylimidazolines from Aromatic Aldehydes
  作者：Babak Kaboudin、Fariba Saadati

  DOI：10.3987/com-04-10203

  日期：——

  A simple, efficient, and new method has been developed for the synthesis of 2,4,5-triarylimidazolines from aldehydes through a one-pot reaction of aldehydes in the presence of alumina-ammonium acetate under solvent-free conditions using microwave irradiation. This method is easy, rapid, one-pot and good to high-yielding reaction for the synthesis of 2,4,5-triarylimidazolines.
• Bertagnini, Justus Liebigs Annalen der Chemie, 1851, vol. 79, p. 266
  作者：Bertagnini

  DOI：——

  日期：——
• Stereoselective synthesis of 1,2-diamino-1,2-diarylethane derivatives
  作者：I. V. Bessonov、N. A. Lozinskaya、V. R. Katashova、M. V. Proskurnina、N. S. Zefirov

  DOI：10.1007/s11172-005-0238-z

  日期：2005.1

  A procedure was developed for selective opening of the cis-2,4,5-triarylimidazoline ring to form erythro-1,2-diamino-1,2-diarylethane derivatives. These ring-opening products, erythro-ethylenediamine derivatives, can undergo quantitative isomerization to threo-ethylenediamine derivatives in the presence of strong bases in DMSO.

  开发了一种选择性打开 cis-2,4,5-三芳基咪唑啉环的方法，以形成 erythro-1,2-二氨基-1,2-二芳基乙烷衍生物。这些开环产物，即 erythro-乙二胺衍生物，可以在 DMSO 中在强碱的存在下发生定量异构化，生成 threo-乙二胺衍生物。
• Antioxidant activity and redox properties of cis-2,4,5-tris(hydroxyaryl)imidazolines
  作者：Daniil R. Bazanov、Victoria Yu. Savitskaya、Natalia A. Maximova、Vladimir Yu. Tyurin、Yulia A. Gracheva、Natalia B. Chesnokova、Olga V. Beznos、Sergey E. Sosonyuk、Natalia A. Lozinskaya

  DOI：10.1016/j.mencom.2022.09.038

  日期：2022.9