1,2-bis-(4-methoxyphenyl)-4-phenyl-2,5-dihydro-1H-imidazole 3-oxide

• 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: 1,2-bis-(4-methoxyphenyl)-4-phenyl-2,5-dihydro-1H-imidazole 3-oxide
• 英文别名: 2,3-Bis(4-methoxyphenyl)-1-oxido-5-phenyl-2,4-dihydroimidazol-1-ium；2,3-bis(4-methoxyphenyl)-1-oxido-5-phenyl-2,4-dihydroimidazol-1-ium
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: UQDPDHAYYIDOAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis-(4-methoxyphenyl)-4-phenyl-2,5-dihydro-1H-imidazole 3-oxide 、 4,4,4-三氟巴豆酸甲酯 以 二氯甲烷 为溶剂， 以92%的产率得到methyl cis-5,6-bis(4-methoxyphenyl)-3a-phenyl-2-(trifluoromethyl)-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylate
  参考文献：
  名称：

  A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles

  摘要：

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.11.002
• 作为产物：
  描述：

  2-bromo-1-phenyl-ethanone oxime 、 4-甲氧基苯甲醛 、 甲氧苯胺 以 乙醇 为溶剂， 反应 3.33h， 生成 1,2-bis-(4-methoxyphenyl)-4-phenyl-2,5-dihydro-1H-imidazole 3-oxide
  参考文献：
  名称：

  A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles

  摘要：

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.11.002

文献信息

• Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides. Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones
  作者：Necdet Coşkun、Habibe Mert、Nevin Arıkan

  DOI：10.1016/j.tet.2005.11.038

  日期：2006.2

  14-Diarylimidazoline 3-oxides react with N-arylmaleimides in benzene to give predominantly the corresponding endo adducts. Chiral imidazoline 3-oxides react diastereospecifically (cis configuration of the tetrahydroimidazo ring) and diastereoselectively to give cis-endo adducts. The effects of substituents on the aromatic ring of the maleimide was investigated. The presence of electron-withdrawing or releasing group,; have minor effect on the total yields but more pronounced is the effect on the ratio of exo and endo diastereomers. The adducts undergo an interesting and unprecedented ring-opening in the presence of secondary amines to give deoxygenated 3-imidazoline 3-oxides instead of the expected double cis elimination products. Tertiary amines did not induce any reaction, (c) 2005 Elsevier Ltd. All rights reserved.
• A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles
  作者：Lei Lu、Weiguo Cao、Jie Chen、Hui Zhang、Jiaping Zhang、Huiyun Chen、Jiamei Wei、Hongmei Deng、Min Shao

  DOI：10.1016/j.jfluchem.2008.11.002

  日期：2009.3

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.