N,N-diethyl-2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetamide | 251909-20-3

• 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: N,N-diethyl-2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetamide
• CAS: 251909-20-3
• 化学式: C₁₅H₂₁F₂NO₄
• 分子量: 317.333
• InChiKey: WXSUEGHMTONZJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetamide 在 sodium hydroxide 、 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]piperidine-2-carboxylic acid 1-phenyl-3-pyridin-3-ylpropyl 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
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 吡啶 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 N,N-diethyl-2,2-difluoro-2-(3,4,5-trimethoxyphenyl)acetamide
  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.