(3R,6S)-4-N-((S)-1-苯乙基)-3-苄基-6-甲基-1,4-吗啉-2,5-二酮 | 174591-38-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (3R,6S)-4-N-((S)-1-苯乙基)-3-苄基-6-甲基-1,4-吗啉-2,5-二酮
• 英文名称: (3R,6S)-4-N-((S)-1-phenethyl)-3-benzyl-6-methyl-1,4-morpholin-2,5-dione
• 英文别名: (3R,6S)-3-benzyl-6-methyl-4-[(1S)-1-phenylethyl]morpholine-2,5-dione
• CAS: 174591-38-9
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: MHPLCSNVVOCORT-RLFYNMQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,6S)-4-N-((S)-1-苯乙基)-3-苄基-6-甲基-1,4-吗啉-2,5-二酮 在 氢碘酸 作用下， 反应 1.0h， 以100%的产率得到D-苯丙氨酸
  参考文献：
  名称：

  Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives

  摘要：

  The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-alpha-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the H-1-NMR data, conformational analysis and nOe measurements.

  DOI：

  10.1016/0957-4166(95)00435-1
• 作为产物：
  描述：

  (4S)-N-((S)-1-phenethyl)-4-phenyl-3-((2S,R)-2-chloropropionyl)-3-aza-ethylpentanoate 在 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (3R,6S)-4-N-((S)-1-苯乙基)-3-苄基-6-甲基-1,4-吗啉-2,5-二酮
  参考文献：
  名称：

  Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives

  摘要：

  The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-alpha-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the H-1-NMR data, conformational analysis and nOe measurements.

  DOI：

  10.1016/0957-4166(95)00435-1

文献信息

• A new stereoselective approach to β-hydroxy-α-aminoacids and dipeptides
  作者：Pina Di Felice、Gianni Porzi、Sergio Sandri

  DOI：10.1016/s0957-4166(99)00211-6

  日期：1999.6

  The chiral synthons 1, 2 and 1' were submitted to aldol condensation to achieve both beta-hydroxy-alpha-aminoacids and dipeptides. The configuration of the new stereogenic centers was assigned on the basis of H-1 NMR spectroscopic data. (C) 1999 Elsevier Science Ltd. All rights reserved.