(5R,4'R,5'S,1''S)-4,5-dihydro-2-(1''-acetamido-3''-methyl-1''-butyl)-5-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazole | 260783-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5R,4'R,5'S,1''S)-4,5-dihydro-2-(1''-acetamido-3''-methyl-1''-butyl)-5-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazole
• 英文别名: N-[(1S)-1-[(5R)-5-[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidine-1-carbonyl]-4,5-dihydro-1,3-oxazol-2-yl]-3-methylbutyl]acetamide
• CAS: 260783-99-1
• 化学式: C₂₂H₃₀N₄O₄
• 分子量: 414.505
• InChiKey: NJZAJPIJBGPHSQ-FZDIXFNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.31
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,4'R,5'S,1''S)-4,5-dihydro-2-(1''-acetamido-3''-methyl-1''-butyl)-5-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazole 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(4R,5S,2'R,2''S)-1,5-dimethyl-3-[3'-(2''-acetamido-4''-methylpentanoyl)amino-2'-hydroxypropionyl]-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

  摘要：

  The ring expansion of 3-unsubstituted (R)-aziridine-2-imide-containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00989-8
• 作为产物：
  描述：

  N-乙酰-L-亮氨酸 在 三氟化硼乙醚 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (5R,4'R,5'S,1''S)-4,5-dihydro-2-(1''-acetamido-3''-methyl-1''-butyl)-5-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]oxazole
  参考文献：
  名称：

  Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

  摘要：

  The ring expansion of 3-unsubstituted (R)-aziridine-2-imide-containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00989-8