(2S)-azido-2-[2-phenyl-4,5-dihydro-oxazol-(4S)-yl]-ethanol | 688308-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-azido-2-[2-phenyl-4,5-dihydro-oxazol-(4S)-yl]-ethanol
• 英文别名: (2S)-2-azido-2-[(4S)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]ethanol
• CAS: 688308-87-4
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: MOKDLEBDDKHJJN-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 (2S)-azido-2-[2-phenyl-4,5-dihydro-oxazol-(4S)-yl]-ethanol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以69%的产率得到p-bromobenzoic acid (2S)-azido-2-[2-phenyl-4,5-dihydro-oxazol-(4S)-yl]-ethyl ester
  参考文献：
  名称：

  Desymmetrisation of C2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde

  摘要：

  Surprisingly, doubly functionalised (2S,3S)-diazidobutane-1,4-diol under modified Boyer conditions reacted with only 1 equiv of benzaldehyde yielding a mono oxazoline, whereas quantum chemical studies favour the formation of the C-2-symmetric bioxazoline. In addition, the oxazoline formation was indirectly confirmed via detailed NMR studies and X-ray structure analysis of the oxazoline p-nitrobenzoic acid ester derivative. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.027
• 作为产物：
  描述：

  苯甲醛 、 (2R,3R)-2,3-diazidobutane-1,4-diol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(2S)-azido-2-[2-phenyl-4,5-dihydro-oxazol-(4S)-yl]-ethanol
  参考文献：
  名称：

  Desymmetrisation of C2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde

  摘要：

  Surprisingly, doubly functionalised (2S,3S)-diazidobutane-1,4-diol under modified Boyer conditions reacted with only 1 equiv of benzaldehyde yielding a mono oxazoline, whereas quantum chemical studies favour the formation of the C-2-symmetric bioxazoline. In addition, the oxazoline formation was indirectly confirmed via detailed NMR studies and X-ray structure analysis of the oxazoline p-nitrobenzoic acid ester derivative. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.027

文献信息

• Desymmetrisation of C2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde
  作者：Andreas Scheurer、Walter Bauer、Frank Hampel、Christine Schmidt、Rolf W. Saalfrank、Paul Mosset、Ralph Puchta、Nico J.R. van Eikema Hommes

  DOI：10.1016/j.tetasy.2004.01.027

  日期：2004.3

  Surprisingly, doubly functionalised (2S,3S)-diazidobutane-1,4-diol under modified Boyer conditions reacted with only 1 equiv of benzaldehyde yielding a mono oxazoline, whereas quantum chemical studies favour the formation of the C-2-symmetric bioxazoline. In addition, the oxazoline formation was indirectly confirmed via detailed NMR studies and X-ray structure analysis of the oxazoline p-nitrobenzoic acid ester derivative. (C) 2004 Elsevier Ltd. All rights reserved.