(trans)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole

• 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: (trans)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
• 英文别名: DL-(4R,5R)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole；(4RS,5RS)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole；(4R,5R)-1-benzyl-2,4,5-triphenyl-4,5-dihydroimidazole
• 化学式: C₂₈H₂₄N₂
• 分子量: 388.512
• InChiKey: VSOVRPJUEZLLSA-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  n-苄基苯甲酰胺 在 2,6-二甲基吡啶 、 草酰氯 、 二氧化碳 、 一氧化碳 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.25h， 生成 (trans)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  亚氨酰氯与氮丙啶扩环一锅合成2-咪唑啉

  摘要：

  我们在此报告了通过亚氨酰氯与氮丙啶的扩环反应（类似于海涅反应）在区域控制和立体定向物质中简单方便地一锅合成高度取代的2-咪唑啉。

  DOI：

  10.1021/jo200101q

文献信息

• Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
  作者：Boran Xu、Kraig Worrall、Bruce Arndtsen

  DOI：10.3390/molecules171213759

  日期：——

  We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl(3) is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates

  我们描述了钯催化的 2-咪唑啉多组分合成。该反应通过亚胺、酰氯和一氧化碳的偶联进行，形成咪唑啉羧酸盐，然后脱羧。发现在 CHCl(3) 中脱羧会产生咪唑啉鎓和咪唑鎓盐的混合物。然而，苯甲酸的加入抑制了芳构化，并以良好的产率生成了反式二取代的咪唑啉。将此反应与随后的氮脱保护相结合，可以从多个可用的结构单元中全面合成咪唑啉。
• Unexpected behaviour of tosylated and acetylated imidazolinium salts
  作者：Nicole Clemens、Oksana Sereda、Ren? Wilhelm

  DOI：10.1039/b601104g

  日期：——

  Tosylated and acetylated imidazolinium salts revealed an unexpected reactivity when treated with methyl iodide or benzyl bromide. Moreover an unprecedented acid-catalysed rearrangement for an acetylated imidazolinium salt was observed during an anion metathesis.

  对甲苯磺酸和乙酰化咪唑啉盐进行甲基碘或苄基溴处理时，反应出乎意料。此外，在阴离子复分解反应中，乙酰化咪唑啉盐发生了前所未有的酸催化重排。
• Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds
  作者：Daljinder K. Kahlon、Theresa A. Lansdell、Jason S. Fisk、Christopher D. Hupp、Timothy L. Friebe、Stacy Hovde、A. Daniel Jones、Richard D. Dyer、R. William Henry、Jetze J. Tepe

  DOI：10.1021/jm8013162

  日期：2009.3.12

  The mammalian nuclear transcription factor NF-kappa B is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-alpha) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-kappa B has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-kappa B mediated gene transcription in cell culture as well as inhibitors of TNF-alpha and IL-6 production in interleukin 1 beta (IL-1 beta) stimulated human blood.
• One-Pot Synthesis of 2-Imidazolines via the Ring Expansion of Imidoyl Chlorides with Aziridines
  作者：Michael R. Kuszpit、William D. Wulff、Jetze J. Tepe

  DOI：10.1021/jo200101q

  日期：2011.4.15

  We herein report a simple and convenient one-pot synthesis of highly substituted 2-imidazolines in a regiocontrolled and stereospecific matter through the ring expansion reaction of an imidoyl chloride with an aziridine, analogous to the Heine reaction.

  我们在此报告了通过亚氨酰氯与氮丙啶的扩环反应（类似于海涅反应）在区域控制和立体定向物质中简单方便地一锅合成高度取代的2-咪唑啉。