(4S,5R,4'S,5'R)-4,5-dihydro-2-methyl-4-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]-5-isopropyloxazole | 347885-30-7

• 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: (4S,5R,4'S,5'R)-4,5-dihydro-2-methyl-4-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]-5-isopropyloxazole
• 英文别名: (4S,5R)-1,5-dimethyl-3-[(4S,5R)-2-methyl-5-propan-2-yl-4,5-dihydro-1,3-oxazole-4-carbonyl]-4-phenylimidazolidin-2-one
• CAS: 347885-30-7
• 化学式: C₁₉H₂₅N₃O₃
• 分子量: 343.426
• InChiKey: WVRQKZZNRJQFTE-VJUNAUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4S,5R,4'S,5'R)-4,5-dihydro-2-methyl-4-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]-5-isopropyloxazole 在 三乙胺 作用下， 反应 2.0h， 生成 (4S,5R)-methyl 5-isopropyl-2-methyl-4,5-dihydrooxazole-4-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor

  摘要：

  The synthesis of syn N-acetyl-hydroxyleucine methyl ester is reported through the ring expansion of aziridine-2-imides to oxazoline-4-imides. The key steps of the synthesis are the I,il-addition of O-benzylhydroxylamine to unsaturated imides, promoted by Lewis acids, and the regio- and stereoselective ring expansion of ti ans-aziridines to trans-oxazolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00084-2
• 作为产物：
  描述：

  (4S,5R,2'S,3'R)-1,5-dimethyl-4-phenyl-3-[(2'-N-acetylaziridinyl-3'-isopropyl)carbonyl]-imidazolidin-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(4S,5R,4'S,5'R)-4,5-dihydro-2-methyl-4-[(1',5'-dimethyl-4'-phenylimidazolidin-2'-on-3'-yl)carbonyl]-5-isopropyloxazole
  参考文献：
  名称：

  Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor

  摘要：

  The synthesis of syn N-acetyl-hydroxyleucine methyl ester is reported through the ring expansion of aziridine-2-imides to oxazoline-4-imides. The key steps of the synthesis are the I,il-addition of O-benzylhydroxylamine to unsaturated imides, promoted by Lewis acids, and the regio- and stereoselective ring expansion of ti ans-aziridines to trans-oxazolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00084-2