(3SR,4SR,5RS)-2,5-dimethyl-3-phenyl-4-(phenylsulfonyl)isoxazolidine | 81650-81-9

• 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: (3SR,4SR,5RS)-2,5-dimethyl-3-phenyl-4-(phenylsulfonyl)isoxazolidine
• CAS: 81650-81-9；81650-82-0
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: NZRIWEJJEFBFHW-XKQJLSEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-(benzylidene)methylamine N-oxide 、 (E)-1-propenyl phenyl sulfone 以 苯 为溶剂， 反应 24.0h， 以2.65 g的产率得到(3SR,4SR,5RS)-2,5-dimethyl-3-phenyl-4-(phenylsulfonyl)isoxazolidine
  参考文献：
  名称：

  Benedetti, Pier G. De; Quartieri, Simona; Rastelli, Augusto, Journal of the Chemical Society. Perkin transactions II, 1982, p. 95 - 100

  摘要：

  DOI：

文献信息

• Nucleophilic additions of lithiated allylphenylsulfone to nitrones: experimental and theoretical investigations
  作者：Pedro Merino、Vanni Mannucci、Tomás Tejero

  DOI：10.1016/j.tet.2005.01.043

  日期：2005.3

  The nucleophilic addition of lithiated allylphenylsulfone to nitrones at -80 degrees C proceeds exclusively a to the phenylsulfonyl group affording anti adducts in high yield. At 0 degrees C isoxazolidines are obtained with complete all-trans selectivity. The formation of these compounds involves isomerization of the allylsulphonyl moiety to give a transient vinylsulfone that then undergoes a subsequent intramolecular Michael addition. The addition to several nitrones has been studied and theoretical calculations have been refined to accurately explain the selectivity of the allylation reaction. (c) 2005 Elsevier Ltd. All rights reserved.