tert-butyl {(3R)-1-[3-(2-chlorobenzyl)-5-methyl-4-oxo-9-phenyl-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl]piperidin-3-yl}carbamate | 1349877-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl {(3R)-1-[3-(2-chlorobenzyl)-5-methyl-4-oxo-9-phenyl-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl]piperidin-3-yl}carbamate
• CAS: 1349877-63-9
• 化学式: C₃₄H₃₆ClN₅O₃
• 分子量: 598.145
• InChiKey: KFXVCTPEVWEPJI-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  43.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.39
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  tert-butyl (R)-(1-(5-([1,1'-biphenyl]-3-yl(methyl)carbamoyl)-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-2-yl)piperidin-3-yl)carbamate 在 palladium diacetate 、 三苯基膦 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 以72%的产率得到tert-butyl {(3R)-1-[3-(2-chlorobenzyl)-5-methyl-4-oxo-7-phenyl-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl]piperidin-3-yl}carbamate
  参考文献：
  名称：

  Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction

  摘要：

  Representatives of the 3H-imidazo[4,5-c]quinolin-4(5H)-ones have shown interesting biological activity. We have found 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-one as a potent dipeptidyl peptidase 4 inhibitor. However effective synthesis of this nucleus with various substituents at the 6-9-positions has not been reported. We report herein the development of a novel and efficient synthesis of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction. Our optimization of the reaction conditions revealed that the most important factors for this reaction are use of silver carbonate as a base and high reaction temperature. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.015