1-[2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid 3-phenyl-1-(2-pyridin-3-yl-ethyl)propyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid 3-phenyl-1-(2-pyridin-3-yl-ethyl)propyl ester
• 英文别名: (1-phenyl-5-pyridin-3-ylpentan-3-yl) (2S)-1-[2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetyl]pyrrolidine-2-carboxylate
• 化学式: C₃₂H₃₆F₂N₂O₆
• 分子量: 582.644
• InChiKey: AQMIJZPOAIOQOZ-AMVUTOCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 吡啶 、 sodium hydroxide 、 selenium(IV) oxide 、 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-[2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid 3-phenyl-1-(2-pyridin-3-yl-ethyl)propyl ester
  参考文献：
  名称：

  2-Aryl-2,2-difluoroacetamide FKBP12 Ligands:  Synthesis and X-ray Structural Studies

  摘要：

  [GRAPHICS]2-Aryl-2,2-difluoroacetamido-proline and pipecolate esters are high affinity FKBP12 ligands whose rotamase inhibitory activity is comparable to that seen for the corresponding ketoamides. X-ray structural studies suggest that the fluorine atoms participate in discrete interactions with the Phe36 phenyl ring and the Tyr26 hydroxyl group, with the latter resembling a moderate-to-weak hydrogen bond.

  DOI：

  10.1021/ol0166909

文献信息

• 2-Aryl-2,2-difluoroacetamide FKBP12 Ligands:  Synthesis and X-ray Structural Studies
  作者：Gene M. Dubowchik、Vivekananda M. Vrudhula、Bireshwar Dasgupta、Jonathan Ditta、Ti Chen、Steven Sheriff、Karin Sipman、Mark Witmer、Jeffrey Tredup、Dolatrai M. Vyas、Todd A. Verdoorn、Sagarika Bollini、Alexander Vinitsky

  DOI：10.1021/ol0166909

  日期：2001.12.1

  [GRAPHICS]2-Aryl-2,2-difluoroacetamido-proline and pipecolate esters are high affinity FKBP12 ligands whose rotamase inhibitory activity is comparable to that seen for the corresponding ketoamides. X-ray structural studies suggest that the fluorine atoms participate in discrete interactions with the Phe36 phenyl ring and the Tyr26 hydroxyl group, with the latter resembling a moderate-to-weak hydrogen bond.