tert-butyl [(3R)-1-{5-[(2-bromophenyl)carbamoyl]-1-(2-chlorobenzyl)-1H-imidazol-2-yl}piperidin-3-yl]carbamate | 1349877-52-6

• 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: tert-butyl [(3R)-1-{5-[(2-bromophenyl)carbamoyl]-1-(2-chlorobenzyl)-1H-imidazol-2-yl}piperidin-3-yl]carbamate
• CAS: 1349877-52-6
• 化学式: C₂₇H₃₁BrClN₅O₃
• 分子量: 588.932
• InChiKey: GVNAKZJIKHORTF-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  88.49
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [(3R)-1-{5-[(2-bromophenyl)carbamoyl]-1-(2-chlorobenzyl)-1H-imidazol-2-yl}piperidin-3-yl]carbamate 在 palladium diacetate 、 碳酸氢钠 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 tert-butyl {(3R)-1-[3-(2-chlorobenzyl)-5-methyl-4-oxo-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
• 作为产物：
  描述：

  2-氯苄溴 在 草酰氯 、 二碘甲烷 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 98.5h， 生成 tert-butyl [(3R)-1-{5-[(2-bromophenyl)carbamoyl]-1-(2-chlorobenzyl)-1H-imidazol-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