2-[3-[3-[2-Ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzonitrile | 1119195-24-2

• 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: 2-[3-[3-[2-Ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzonitrile
• CAS: 1119195-24-2
• 化学式: C₃₃H₃₂FNO₄
• 分子量: 525.62
• InChiKey: URMKMGPXZBTDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[3-[3-[2-Ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzonitrile 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.5h， 以99%的产率得到2-[3-[3-[2-乙基-4-(4-氟苯基)-5-羟基苯氧基]丙氧基]-2-丙基苯氧基]苯甲酸
  参考文献：
  名称：

  An Efficient Synthesis of a Multipotent Eicosanoid Pathway Modulator

  摘要：

  An efficient, scalable synthesis of the multipotent eicosanoid pathway modulator 2-[3-[3[[5-ethyl-4'-fluoro-2-hydroxyl[1,1'-bi-phenyl]-4-yl]oxy]-propoxy]2-propoxylphenoxy]benzoic acid (1) is described. The process consists of nine chemical steps with the longest linear sequence having six isolations. Palladium metal-mediated cross-coupling assembles the biaryl fragment, and selective S(N)Ar chemistry is used to construct the resorcinol fragment. The synthesis converges at a phenolic coupling with an alkyl chloride to give the core structure of the active pharmaceutical ingredient (API). Further elaborations of the core and salt formation provides the final API. This process produced the drug candidate in 41% overall yield at multikilogram scale.

  DOI：

  10.1021/op800257u
• 作为产物：
  描述：

  2-[3-[3-[[5-ethyl-4'-fluoro-2-(phenylmethoxy)[1,1'-biphenyl]-4-yl]oxy]-propoxy]-2-propoxyphenoxy]benzonitrile 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以96%的产率得到2-[3-[3-[2-Ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzonitrile
  参考文献：
  名称：

  An Efficient Synthesis of a Multipotent Eicosanoid Pathway Modulator

  摘要：

  An efficient, scalable synthesis of the multipotent eicosanoid pathway modulator 2-[3-[3[[5-ethyl-4'-fluoro-2-hydroxyl[1,1'-bi-phenyl]-4-yl]oxy]-propoxy]2-propoxylphenoxy]benzoic acid (1) is described. The process consists of nine chemical steps with the longest linear sequence having six isolations. Palladium metal-mediated cross-coupling assembles the biaryl fragment, and selective S(N)Ar chemistry is used to construct the resorcinol fragment. The synthesis converges at a phenolic coupling with an alkyl chloride to give the core structure of the active pharmaceutical ingredient (API). Further elaborations of the core and salt formation provides the final API. This process produced the drug candidate in 41% overall yield at multikilogram scale.

  DOI：

  10.1021/op800257u