N-<(R)-α-methylbenzyl>-2-(hydroxyimino)butanamide | 131490-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-<(R)-α-methylbenzyl>-2-(hydroxyimino)butanamide
• 英文别名: N-((R)-α-methylbenzyl)-2-(hydroxyimino)butanamide
• CAS: 131490-82-9
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: JHMNRPSRVJUXKP-CSCQJOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-<(R)-α-methylbenzyl>-2-(hydroxyimino)butanamide 、 4-甲氧基苯甲醛 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 (4S,5S)-(+)-4,5-dihydro-5-(4-methoxyphenyl)-4-methyl-N-<(R)-1-phenylethyl>isoxazole-3-carboxamide 、 (4S,5S)-4,5-Dihydro-5-(4-methoxyphenyl)-4-methyl-N-<(S)-1-phenylethyl>-3-isoxazolcarboxamide
  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：

  2-酮丁酸 、 R(+)-alpha-甲基苄胺 、 三乙胺 生成 N-<(R)-α-methylbenzyl>-2-(hydroxyimino)butanamide
  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