3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanamide | 1338442-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanamide
• CAS: 1338442-65-1
• 化学式: C₂₄H₃₂N₂O₂
• 分子量: 380.53
• InChiKey: JTHOGJWTVIFYSK-XJNFMUPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  pseudopterosin Y aglycone 在 ammonium cerium (IV) nitrate 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanamide
  参考文献：
  名称：

  One-Pot Syntheses of Pseudopteroxazoles from Pseudopterosins: A Rapid Route to Non-natural Congeners with Improved Antimicrobial Activity

  摘要：

  Rapid one-pot methodologies to prepare pseudopteroxazole (1) and novel congeners from abundant natural pseudopterosins have been devised. This is highlighted here with the first synthesis of the marine natural product homopseudopteroxazole (2) utilizing a novel, silver(I)-mediated catechol to benzoxazole transformation. Pseudopteroxazoles and isopseudopteroxazoles exhibit potent activity against a range of important Gram-positive pathogens including Mycobacterium spp. and vancomycin-resistant Enterococcus faecium. Several non-natural pseudopteroxazoles exhibited strong activity against methicillin-resistant Staphylococcus aureus, thereby displaying a broader spectrum of antibiotic activity compared to pseudopteroxazole.

  DOI：

  10.1021/np2006555

文献信息

• One-Pot Syntheses of Pseudopteroxazoles from Pseudopterosins: A Rapid Route to Non-natural Congeners with Improved Antimicrobial Activity
  作者：Malcolm W. B. McCulloch、Fabrice Berrue、Brad Haltli、Russell G. Kerr

  DOI：10.1021/np2006555

  日期：2011.10.28

  Rapid one-pot methodologies to prepare pseudopteroxazole (1) and novel congeners from abundant natural pseudopterosins have been devised. This is highlighted here with the first synthesis of the marine natural product homopseudopteroxazole (2) utilizing a novel, silver(I)-mediated catechol to benzoxazole transformation. Pseudopteroxazoles and isopseudopteroxazoles exhibit potent activity against a range of important Gram-positive pathogens including Mycobacterium spp. and vancomycin-resistant Enterococcus faecium. Several non-natural pseudopteroxazoles exhibited strong activity against methicillin-resistant Staphylococcus aureus, thereby displaying a broader spectrum of antibiotic activity compared to pseudopteroxazole.