2-(3,5-Difluoro-phenyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester | 848188-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,5-Difluoro-phenyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester
• CAS: 848188-33-0
• 化学式: C₁₈H₁₃F₂NO₃
• 分子量: 329.303
• InChiKey: PBKLYWQXYXFKTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3,5-Difluoro-phenyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 2-(3,5-Difluoro-phenyl)-5-methyl-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors

  摘要：

  Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amyloidogenesis. The efficacy of these inhibitors was enhanced further by installing an ethyl, a propyl, or a CF3 group at the C(5) position. The CF3 substitution at C(5) also improves the TTR binding selectivity over all the other proteins in human blood. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.022
• 作为产物：
  描述：

  3,5-二氟苯甲酰氯 在 伯吉斯试剂 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(3,5-Difluoro-phenyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors

  摘要：

  Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amyloidogenesis. The efficacy of these inhibitors was enhanced further by installing an ethyl, a propyl, or a CF3 group at the C(5) position. The CF3 substitution at C(5) also improves the TTR binding selectivity over all the other proteins in human blood. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.022