methyl 2-[4-[3,3-dimethyl-1-[4-(trifluoromethyl)piperidin-1-yl]butyl]-3-[4-(trifluoromethyl)phenyl]phenyl]acetate | 1361049-23-1

• 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: methyl 2-[4-[3,3-dimethyl-1-[4-(trifluoromethyl)piperidin-1-yl]butyl]-3-[4-(trifluoromethyl)phenyl]phenyl]acetate
• CAS: 1361049-23-1
• 化学式: C₂₈H₃₃F₆NO₂
• 分子量: 529.566
• InChiKey: DORVJJIRLMKEOP-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±50.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-[3,3-dimethyl-1-[4-(trifluoromethyl)piperidin-1-yl]butyl]-3-[4-(trifluoromethyl)phenyl]phenyl]acetate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到2-(6-(3,3-dimethyl-1-(4-(trifluoromethyl)piperidin-1-yl)butyl)-4'-(trifluoromethyl)biphenyl-3-yl)acetic acid
  参考文献：
  名称：

  Discovery of 4-aminomethylphenylacetic acids as γ-secretase modulators via a scaffold design approach

  摘要：

  Starting from literature examples of nonsteroidal anti-inflammatory drugs (NSAIDs)-type carboxylic acid gamma-secretase modulators (GSMs) and using a scaffold design approach, we identified 4-aminomethylphenylacetic acid 4 with a desirable gamma-secretase modulation profile. Scaffold optimization led to the discovery of a novel chemical series, represented by 6b, having improved brain penetration. Further SAR studies provided analog 6q that exhibited a good pharmacological profile. Oral administration of 6q significantly reduced brain A beta 42 levels in mice and rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.047
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 在 吡啶 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 、 diborane(6) 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 methyl 2-[4-[3,3-dimethyl-1-[4-(trifluoromethyl)piperidin-1-yl]butyl]-3-[4-(trifluoromethyl)phenyl]phenyl]acetate
  参考文献：
  名称：

  Discovery of 4-aminomethylphenylacetic acids as γ-secretase modulators via a scaffold design approach

  摘要：

  Starting from literature examples of nonsteroidal anti-inflammatory drugs (NSAIDs)-type carboxylic acid gamma-secretase modulators (GSMs) and using a scaffold design approach, we identified 4-aminomethylphenylacetic acid 4 with a desirable gamma-secretase modulation profile. Scaffold optimization led to the discovery of a novel chemical series, represented by 6b, having improved brain penetration. Further SAR studies provided analog 6q that exhibited a good pharmacological profile. Oral administration of 6q significantly reduced brain A beta 42 levels in mice and rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.047