(3'R,4S,4'S,5'R)-4-benzyl-3-((5'-methyl-2',3'-diphenylisoxazolidin-4'-yl)carbonyl)-1,3-oxazolidin-2-one | 241822-41-3

• 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: (3'R,4S,4'S,5'R)-4-benzyl-3-((5'-methyl-2',3'-diphenylisoxazolidin-4'-yl)carbonyl)-1,3-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(3R,4S,5R)-5-methyl-2,3-diphenyl-1,2-oxazolidine-4-carbonyl]-1,3-oxazolidin-2-one
• CAS: 241822-41-3
• 化学式: C₂₇H₂₆N₂O₄
• 分子量: 442.514
• InChiKey: FZTUKBIQIYJLJY-MNVNNWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异丙醇 、 (3'R,4S,4'S,5'R)-4-benzyl-3-((5'-methyl-2',3'-diphenylisoxazolidin-4'-yl)carbonyl)-1,3-oxazolidin-2-one 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以91%的产率得到(3R,4S,5R)-4-isoxazolidinecarboxylic acid, 5-methyl-2,3-diphenyl-, isopropyl ester
  参考文献：
  名称：

  Control of diastereoselectivity in metal-catalyzed 1,3-dipolar cycloaddition between diphenylnitrone and chiral auxiliary-substituted crotonyl amide

  摘要：

  The 1,3-dipolar cycloaddition (1,3-DC) between diphenyl nitrone (1) and 4-(S)-benzyl-((E)-2'-butenoyl)- 1,3-oxazolidin-2-one (2) was studied in the presence of several inorganic salts whose cations behave as Lewis acid, Depending on the salt and the experimental conditions, three products (3-5) can be obtained diastereoselectively. The type of conformation assumed by 2 when coordinated to the cation, allows the attack of 1 on either the Re- or the Si-face of the dipolarophile and rationalizes the resulting diastereoselectivity. The coordination of the reagents around the cation was studied by NMR spectroscopy with 2-acetyl-4-(S)-benzyl-1,3-oxazolidin-2-one (7) as model compound, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00469-x
• 作为产物：
  描述：

  (4S)-N-巴豆酰基-4-异丙基-2-恶唑烷酮 、 C,N-diphenylnitrone 在 magnesium(II) perchlorate 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 (3'R,4S,4'S,5'R)-4-benzyl-3-((5'-methyl-2',3'-diphenylisoxazolidin-4'-yl)carbonyl)-1,3-oxazolidin-2-one 、 (3'S,4S,4'S,5'R)-4-benzyl-3-((5'-methyl-2',3'-diphenylisoxazolidin-4'-yl)carbonyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Control of diastereoselectivity in metal-catalyzed 1,3-dipolar cycloaddition between diphenylnitrone and chiral auxiliary-substituted crotonyl amide

  摘要：

  The 1,3-dipolar cycloaddition (1,3-DC) between diphenyl nitrone (1) and 4-(S)-benzyl-((E)-2'-butenoyl)- 1,3-oxazolidin-2-one (2) was studied in the presence of several inorganic salts whose cations behave as Lewis acid, Depending on the salt and the experimental conditions, three products (3-5) can be obtained diastereoselectively. The type of conformation assumed by 2 when coordinated to the cation, allows the attack of 1 on either the Re- or the Si-face of the dipolarophile and rationalizes the resulting diastereoselectivity. The coordination of the reagents around the cation was studied by NMR spectroscopy with 2-acetyl-4-(S)-benzyl-1,3-oxazolidin-2-one (7) as model compound, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00469-x