benzyl 4-(2-acetoxy-5-(4-chlorophenyl)-1H-pyrrol-1-yl)benzoate | 1191053-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: benzyl 4-(2-acetoxy-5-(4-chlorophenyl)-1H-pyrrol-1-yl)benzoate
• 英文别名: Benzyl 4-[2-acetyloxy-5-(4-chlorophenyl)pyrrol-1-yl]benzoate
• CAS: 1191053-08-3
• 化学式: C₂₆H₂₀ClNO₄
• 分子量: 445.902
• InChiKey: ZNRNBZJWRWZYBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 4-(2-acetoxy-5-(4-chlorophenyl)-1H-pyrrol-1-yl)benzoate 、 5-(4-溴苯基)-2-呋喃甲醛 在 sodium acetate 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以14%的产率得到(Z)-benzyl 4-(3-((5-(4-bromophenyl)furan-2-yl)methylene)-5-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-pyrrol-1-yl)benzoate
  参考文献：
  名称：

  Investigation of N-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics

  摘要：

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.

  DOI：

  10.1021/jm900707n
• 作为产物：
  描述：

  benzyl 4-(4-(4-chlorophenyl)-4-oxobutanamido)benzoate 、 乙酰氯 在 4-二甲氨基吡啶 作用下， 反应 15.0h， 以75%的产率得到benzyl 4-(2-acetoxy-5-(4-chlorophenyl)-1H-pyrrol-1-yl)benzoate
  参考文献：
  名称：

  Investigation of N-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics

  摘要：

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.

  DOI：

  10.1021/jm900707n