3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid | 1262547-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid
• 英文别名: 3-[2-[3-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propyl]-1,3-benzoxazol-5-yl]propanoic acid
• CAS: 1262547-40-9
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: KRFWKTVKRYKPKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid 在 正丁基锂 、 偶氮二甲酸二异丙酯 、 乙基溴化镁 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 18.17h， 生成 (S)-methyl 2-(2-bromophenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives

  摘要：

  Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.028
• 作为产物：
  描述：

  methyl 3-(2-(chloromethyl)benzo[d]oxazol-5-yl)propanoate 在 lithium hydroxide monohydrate 、 platinum(IV) oxide trihydrate 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -10.0~150.0 ℃ 、101.33 kPa 条件下， 反应 17.17h， 生成 3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives

  摘要：

  Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.028