2-(1-phenylethylideneaminoxymethyl)-3-hydroxy-3-(4-nitrophenyl)propanoate

• 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: 2-(1-phenylethylideneaminoxymethyl)-3-hydroxy-3-(4-nitrophenyl)propanoate
• 英文别名: (3S,4S)-4-hydroxy-4-(4-nitrophenyl)-3-[[(E)-1-phenylethylideneamino]oxymethyl]butan-2-one
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: YMTFWRQAOLDOFR-ZWWAOTTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯乙酮肟 、 3-[羟基-(4-硝基苯基)甲基]丁-3-烯-2-酮 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 2-(1-phenylethylideneaminoxymethyl)-3-hydroxy-3-(4-nitrophenyl)propanoate 、 2-(1-phenylethylideneaminoxymethyl)-3-hydroxy-3-(4-nitrophenyl)propanoate
  参考文献：
  名称：

  Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts

  摘要：

  Triphenylphosphine-catalyzed Michael addition of oximes 2 onto Baylis-Hillman (B-H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen-centered nucleophile in Michael addition to B-H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3-diols 4 as potentially useful synthons with optional backbone choice (R 3 and EWG).

  DOI：

  10.1080/00397910500334132

文献信息

• Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts
  作者：Debnath Bhuniya、Srinivas Gujjary、Sujata Sengupta

  DOI：10.1080/00397910500334132

  日期：2006.2.1

  Triphenylphosphine-catalyzed Michael addition of oximes 2 onto Baylis-Hillman (B-H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen-centered nucleophile in Michael addition to B-H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3-diols 4 as potentially useful synthons with optional backbone choice (R 3 and EWG).