(Z)-2-(4-Benzyloxy-3,5-diisopropyl-benzyl)-3-morpholin-4-yl-acrylonitrile | 110798-46-4

• 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: (Z)-2-(4-Benzyloxy-3,5-diisopropyl-benzyl)-3-morpholin-4-yl-acrylonitrile
• 英文别名: 3-anilino-2-<4-(benzyloxy)-3,5-diisopropylbenzyl>acrylonitrile；3-anilino-2-[4-(benzyloxy)-3,5-diisopropylbenzyl]acrylonitrile
• CAS: 110798-46-4
• 化学式: C₂₉H₃₂N₂O
• 分子量: 424.586
• InChiKey: DSAGBPVIYAVBLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  45.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 (Z)-2-(4-Benzyloxy-3,5-diisopropyl-benzyl)-3-morpholin-4-yl-acrylonitrile 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以89%的产率得到2,4-diamino-5-<4-(benzyloxy)-3,5-diisopropylbenzyl>pyrimidine
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 9. Lipophilic trimethoprim analogs as antigonococcal agents

  摘要：

  Lipophilic analogues of trimethoprim (1) bearing 3,5-dialkyl-4-hydroxy substituents in the benzene ring are much more active in vitro against Neisseria gonorrhoeae than is 1. The 3,5-diisopropyl-4-hydroxy derivative (2) was selected as a candidate for clinical evaluation as an antigonococcal agent, and as part of the preliminary evaluation it was submitted to extended pharmacokinetic and metabolism studies in dogs. Although the compound was not extensively conjugated by metabolic enzymes, one of the methyl groups was metabolized to produce a 3-isopropyl-4-hydroxy-5-(alpha-carboxyethyl)benzyl derivative (43), which was rapidly excreted. Related analogues were likewise extensively metabolized.

  DOI：

  10.1021/jm00396a018
• 作为产物：
  描述：

  丙泊酚 在 盐酸 、 sodium methylate 、 sodium hydride 、 氯化铵 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.25h， 生成 (Z)-2-(4-Benzyloxy-3,5-diisopropyl-benzyl)-3-morpholin-4-yl-acrylonitrile
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 9. Lipophilic trimethoprim analogs as antigonococcal agents

  摘要：

  Lipophilic analogues of trimethoprim (1) bearing 3,5-dialkyl-4-hydroxy substituents in the benzene ring are much more active in vitro against Neisseria gonorrhoeae than is 1. The 3,5-diisopropyl-4-hydroxy derivative (2) was selected as a candidate for clinical evaluation as an antigonococcal agent, and as part of the preliminary evaluation it was submitted to extended pharmacokinetic and metabolism studies in dogs. Although the compound was not extensively conjugated by metabolic enzymes, one of the methyl groups was metabolized to produce a 3-isopropyl-4-hydroxy-5-(alpha-carboxyethyl)benzyl derivative (43), which was rapidly excreted. Related analogues were likewise extensively metabolized.

  DOI：

  10.1021/jm00396a018