(2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one | 479191-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one
• 英文别名: (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenylimidazolidin-4-one
• CAS: 479191-76-9
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: VPJDHSYHSYIZAX-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 在 T406石油添加剂 、 三氯化铝 作用下， 以 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到(3S,10aS)-2-(4-methylphenyl)-3-phenyl-2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-one
  参考文献：
  名称：

  Novel Syntheses of Enantiopure Hexahydroimidazo[1,5-b]isoquinolines and Tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via Iminium Cation Cyclizations

  摘要：

  Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of alpha-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.

  DOI：

  10.1021/jo0203241
• 作为产物：
  描述：

  tert-butyl N-[(1S)-1-benzyl-2-oxo-2-(4-toluidino)ethyl]carbamate 在 三氯化铝 、 对甲苯磺酸 、 sodium sulfate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one
  参考文献：
  名称：

  Novel Syntheses of Enantiopure Hexahydroimidazo[1,5-b]isoquinolines and Tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via Iminium Cation Cyclizations

  摘要：

  Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of alpha-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.

  DOI：

  10.1021/jo0203241

文献信息

• Novel Syntheses of Enantiopure Hexahydroimidazo[1,5-<i>b</i>]isoquinolines and Tetrahydroimidazo[1,5-<i>b</i>]isoquinolin-1(5<i>H</i>)-ones via Iminium Cation Cyclizations
  作者：Alan R. Katritzky、Kazuyuki Suzuki、Hai-Ying He

  DOI：10.1021/jo0203241

  日期：2002.11.1

  Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of alpha-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.