5-乙氧基-2-甲基-3-苯基-1,2-恶唑烷 | 215509-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-乙氧基-2-甲基-3-苯基-1,2-恶唑烷
• 英文名称: 5-Ethoxy-2-methyl-3-phenylisoxazolidine
• 英文别名: 5-ethoxy-2-methyl-3-phenyl-1,2-oxazolidine
• CAS: 215509-17-4
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: NHILOZCLSIHIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-乙氧基-2-甲基-3-苯基-1,2-恶唑烷 在 硫酸 作用下， 反应 1.75h， 以100%的产率得到C-styryl-N-methyl nitrone
  参考文献：
  名称：

  Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines.

  摘要：

  High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.

  DOI：

  10.1016/s0040-4020(01)88315-0
• 作为产物：
  描述：

  N-methyl-α-phenylnitrone 、 乙烯基乙醚 在 1-正丁基-3-甲基咪唑三氟甲烷磺酸盐 、 erbium(III) triflate 作用下， 反应 1.0h， 生成 5-乙氧基-2-甲基-3-苯基-1,2-恶唑烷
  参考文献：
  名称：

  1,3-Cycloaddition of nitrones in ionic liquids catalyzed by Er(III): an easy access to isoxazolidines

  摘要：

  1, 3-Dipolar cycloadditions of nitrones with alkenes afforded the corresponding isoxazolidines in ionic liquids in the presence of Er(OTf)(3). The ionic liquid and the catalyst are recycled up to five times without any specific treatment or loss of activity. Extension of the procedure to the synthesis of isoxazolidinyl nucleosides has been investigated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.219

文献信息

• DICKEN, C. M.;DESHONG, P., J. ORG. CHEM., 1982, 47, N 11, 2047-2051
  作者：DICKEN, C. M.、DESHONG, P.

  DOI：——

  日期：——
• Ring-opening of isoxazolidine system: Homologation of 3-aryl into 3-styryl nitrones via intermediate 5-hydroxy-isoxazolidines.
  作者：Ugo Chiacchio、Angelo Liguori、Giovanni Romeo、Giovanni Sindona、Nicola Uccella

  DOI：10.1016/s0040-4020(01)88315-0

  日期：1992.1

  High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.
• 1,3-Cycloaddition of nitrones in ionic liquids catalyzed by Er(III): an easy access to isoxazolidines
  作者：Olga Bortolini、Antonio De Nino、Loredana Maiuolo、Beatrice Russo、Giovanni Sindona、Amedeo Tocci

  DOI：10.1016/j.tetlet.2007.07.219

  日期：2007.10

  1, 3-Dipolar cycloadditions of nitrones with alkenes afforded the corresponding isoxazolidines in ionic liquids in the presence of Er(OTf)(3). The ionic liquid and the catalyst are recycled up to five times without any specific treatment or loss of activity. Extension of the procedure to the synthesis of isoxazolidinyl nucleosides has been investigated. (c) 2007 Elsevier Ltd. All rights reserved.