<4(S,R),5(S,R)>-5-(4-hydroxyphenyl)-4-methyl-N-tert-butylisoxazolecarboxamide | 131490-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: <4(S,R),5(S,R)>-5-(4-hydroxyphenyl)-4-methyl-N-tert-butylisoxazolecarboxamide
• CAS: 131490-79-4
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: BCZTVLZAMRYPCA-ZANVPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  70.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <4(S,R),5(S,R)>-5-(4-hydroxyphenyl)-4-methyl-N-tert-butylisoxazolecarboxamide 在 sodium hydroxide 、 氢溴酸 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 61.0h， 生成 <3(S,R),4(S,R),5(S,R)>-3-amino-5-(4-hydroxyphenyl)-4-methyltetrahydrofuran-2-one hydrobromide
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042
• 作为产物：
  描述：

  N-tert-butyl-2-(hydroxyimino)butanamide 在 正丁基锂 、 四甲基乙二胺 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 <4(S,R),5(S,R)>-5-(4-hydroxyphenyl)-4-methyl-N-tert-butylisoxazolecarboxamide
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042