1-(4-chlorophenyl)-2-((diallylamino)methyl)-3-methylbutan-1-one | 1394018-12-2

• 英文名称: 1-(4-chlorophenyl)-2-((diallylamino)methyl)-3-methylbutan-1-one
• CAS: 1394018-12-2
• 化学式: C₁₈H₂₄ClNO
• 分子量: 305.848
• InChiKey: UMQLWCUWIFANGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-((diallylamino)methyl)-3-methylbutan-1-one 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(2-(4-chlorobenzoyl)-3-methylbutyl)-2-methylbenzamide
  参考文献：
  名称：

  N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor

  摘要：

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.032
• 作为产物：
  描述：

  聚合甲醛 、 1-(4-氯苯基)-3-甲基丁烷-1-酮 、 二烯丙基胺 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以32.3%的产率得到1-(4-chlorophenyl)-2-((diallylamino)methyl)-3-methylbutan-1-one
  参考文献：
  名称：

  N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor

  摘要：

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.032