(S)-methyl 2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate | 1262547-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-methyl 2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate
• CAS: 1262547-55-6
• 化学式: C₃₂H₃₀N₂O₆
• 分子量: 538.6
• InChiKey: GLFVZNCMTNOWKL-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104.66
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以71%的产率得到(S)-2-(4-acetylphenoxy)-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
• 作为产物：
  描述：

  methyl 3-(3-amino-4-hydroxyphenyl)propanoate 在 正丁基锂 、 lithium hydroxide monohydrate 、 platinum(IV) oxide trihydrate 、 偶氮二甲酸二异丙酯 、 乙基溴化镁 、 potassium tert-butylate 、 氢气 、 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 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~150.0 ℃ 、101.33 kPa 条件下， 反应 36.84h， 生成 (S)-methyl 2-(4-acetylphenoxy)-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