2,4,6-trimethylphenyl 5-(4-methylphenyl)-4-phenyl-1-(2-pyridinesulfonyl)-4,5-dihydro-1H-4-imidazolecarboxylate

• 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: 2,4,6-trimethylphenyl 5-(4-methylphenyl)-4-phenyl-1-(2-pyridinesulfonyl)-4,5-dihydro-1H-4-imidazolecarboxylate
• 英文别名: (2,4,6-trimethylphenyl) (4S,5R)-4-(4-methylphenyl)-5-phenyl-3-pyridin-2-ylsulfonyl-4H-imidazole-5-carboxylate
• 化学式: C₃₁H₂₉N₃O₄S
• 分子量: 539.655
• InChiKey: MBQJXRFKLGHEGV-IGYGKHONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-N-(4-methylbenzylidene)pyridine-2-sulfonamide 、 (+/-)-2,4,6-trimethylphenyl 2-isocyano-2-phenylacetate 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以83%的产率得到2,4,6-trimethylphenyl 5-(4-methylphenyl)-4-phenyl-1-(2-pyridinesulfonyl)-4,5-dihydro-1H-4-imidazolecarboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Imidazolines with Quaternary Stereocenters by Organocatalytic Reaction of N-(Heteroarenesulfonyl)imines with Isocyanoacetates

  摘要：

  An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related alpha,beta-diamino acids having a quaternary carbon center in high enantiomeric purities.

  DOI：

  10.1021/ol301256q

文献信息

• Enantioselective Synthesis of Imidazolines with Quaternary Stereocenters by Organocatalytic Reaction of <i>N</i>-(Heteroarenesulfonyl)imines with Isocyanoacetates
  作者：Shuichi Nakamura、Yuri Maeno、Mutsuyo Ohara、Akiko Yamamura、Yasuhiro Funahashi、Norio Shibata

  DOI：10.1021/ol301256q

  日期：2012.6.15

  An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related alpha,beta-diamino acids having a quaternary carbon center in high enantiomeric purities.