methyl (3R,5R)-5-[(1R,2S)-2-(benzyloxy)-1-fluoropropyl]-2-methyl-3-phenyltetrahydro-5-isoxazolecarboxylate | 673474-62-9

• 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: methyl (3R,5R)-5-[(1R,2S)-2-(benzyloxy)-1-fluoropropyl]-2-methyl-3-phenyltetrahydro-5-isoxazolecarboxylate
• 英文别名: methyl (3R,5R)-5-[(1R,2S)-1-fluoro-2-phenylmethoxypropyl]-2-methyl-3-phenyl-1,2-oxazolidine-5-carboxylate
• CAS: 673474-62-9
• 化学式: C₂₂H₂₆FNO₄
• 分子量: 387.451
• InChiKey: SLMIGJYTZRGJAH-DQMRONCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3R,5R)-5-[(1R,2S)-2-(benzyloxy)-1-fluoropropyl]-2-methyl-3-phenyltetrahydro-5-isoxazolecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以81%的产率得到(2R,3R,4S)-4-(benzyloxy)-3-fluoro-2-[(2R)-2-(methylamino)-2-phenylethyl]-1,2-pentanediol
  参考文献：
  名称：

  First 1,3-dipolar cycloaddition of Z-α-phenyl-N-methylnitrone with allylic fluorides: a stereoselective route to enantiopure fluorine-containing isoxazolidines and amino polyols

  摘要：

  Enantiopure fluorinated isoxazolidines and amino polyols were obtained from the 1,3-dipolar cycloaddition of allylic fluorides and Z-alpha-phenyl-N-methylnitrone under environment-friendly conditions. (C) 2003 Elsevier Ltd. All right reserved.

  DOI：

  10.1016/j.tetasy.2003.11.008
• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 在 In(OSO₂CF₃)3 三乙烯二胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 342.42h， 生成 methyl (3R,5R)-5-[(1R,2S)-2-(benzyloxy)-1-fluoropropyl]-2-methyl-3-phenyltetrahydro-5-isoxazolecarboxylate
  参考文献：
  名称：

  First 1,3-dipolar cycloaddition of Z-α-phenyl-N-methylnitrone with allylic fluorides: a stereoselective route to enantiopure fluorine-containing isoxazolidines and amino polyols

  摘要：

  Enantiopure fluorinated isoxazolidines and amino polyols were obtained from the 1,3-dipolar cycloaddition of allylic fluorides and Z-alpha-phenyl-N-methylnitrone under environment-friendly conditions. (C) 2003 Elsevier Ltd. All right reserved.

  DOI：

  10.1016/j.tetasy.2003.11.008

文献信息

• First 1,3-dipolar cycloaddition of Z-α-phenyl-N-methylnitrone with allylic fluorides: a stereoselective route to enantiopure fluorine-containing isoxazolidines and amino polyols
  作者：Luca Bernardi、Bianca F. Bonini、Mauro Comes-Franchini、Mariafrancesca Fochi、Mahena Folegatti、Stefano Grilli、Andrea Mazzanti、Alfredo Ricci

  DOI：10.1016/j.tetasy.2003.11.008

  日期：2004.1

  Enantiopure fluorinated isoxazolidines and amino polyols were obtained from the 1,3-dipolar cycloaddition of allylic fluorides and Z-alpha-phenyl-N-methylnitrone under environment-friendly conditions. (C) 2003 Elsevier Ltd. All right reserved.