(4S,5R)-3-Ethenesulfonyl-4-methyl-5-phenyl-oxazolidin-2-one | 379693-23-9

• 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: (4S,5R)-3-Ethenesulfonyl-4-methyl-5-phenyl-oxazolidin-2-one
• 英文别名: (4S,5R)-3-ethenylsulfonyl-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 379693-23-9
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: RDPVJJKFVIEUOF-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 (4S,5R)-3-Ethenesulfonyl-4-methyl-5-phenyl-oxazolidin-2-one 在 二氯乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 以51%的产率得到(4S,5R)-3-[[(1R,2R,4R)-2-bicyclo[2.2.1]hept-5-enyl]sulfonyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Diels–Alder reactions of optically active oxazolidinone-derived vinylsulfonamides

  摘要：

  Chiral vinylsulfonamides bearing an oxazolidin-2-one moiety derived from (R)-2-phenylglycinol and (1R,2S)norephedrine have been employed as dienophiles in asymmetric Diels-Alder reactions at normal pressure affording d.e.s of up to 99% when EtAlCl2 or Et2AlCl were employed as Lewis acids. Theoretical calculations justify the observed enantio- and diastereoselectivity. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00320-2
• 作为产物：
  描述：

  去甲麻黄碱 在 sodium hydride 、 三乙胺 作用下， 生成 (4S,5R)-3-Ethenesulfonyl-4-methyl-5-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Diels–Alder reactions of optically active oxazolidinone-derived vinylsulfonamides

  摘要：

  Chiral vinylsulfonamides bearing an oxazolidin-2-one moiety derived from (R)-2-phenylglycinol and (1R,2S)norephedrine have been employed as dienophiles in asymmetric Diels-Alder reactions at normal pressure affording d.e.s of up to 99% when EtAlCl2 or Et2AlCl were employed as Lewis acids. Theoretical calculations justify the observed enantio- and diastereoselectivity. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00320-2

文献信息

• Asymmetric Diels–Alder reactions of optically active oxazolidinone-derived vinylsulfonamides
  作者：M.Carmen Bernabeu、Rafael Chinchilla、Larry R. Falvello、Carmen Nájera

  DOI：10.1016/s0957-4166(01)00320-2

  日期：2001.7

  Chiral vinylsulfonamides bearing an oxazolidin-2-one moiety derived from (R)-2-phenylglycinol and (1R,2S)norephedrine have been employed as dienophiles in asymmetric Diels-Alder reactions at normal pressure affording d.e.s of up to 99% when EtAlCl2 or Et2AlCl were employed as Lewis acids. Theoretical calculations justify the observed enantio- and diastereoselectivity. (C) 2001 Published by Elsevier Science Ltd.