2-ethyl-1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxybutane | 324518-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-ethyl-1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxybutane
• 英文别名: 2-(3,3-diethyloxiran-2-yl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 324518-96-9
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: AZBFQNBHWCCRJY-UHFFFAOYSA-N

物化性质

• 沸点：
  244.7±33.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxybutane 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 3.25h， 以80%的产率得到1-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-2-ethylbutan-1-one
  参考文献：
  名称：

  Oxiranyllithium based synthesis of α-keto-2-oxazolines

  摘要：

  alpha -Keto-2-oxazolines 5a-j have been efficiently prepared by lithiation [sec-(or n-)BuLi/TMEDA, Et2O, -100 degreesC] and rearrangement of oxiranyl oxazolines 2a-j. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01558-6
• 作为产物：
  描述：

  二苯甲酮 、 2-chloromethyl-4,4-dimethyl-4,5-dihydro-1,3-oxazole 在 lithium diisopropyl amide 、 sodium hydroxide 、 异丙醇 作用下， 以86%的产率得到2-ethyl-1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxybutane
  参考文献：
  名称：

  由恶唑啉基恶拉宁合成烯丙基醇。

  摘要：

  二乙醚中的二异丙基氨基化锂（LDA）（或s-BuLi / TMEDA）促进了恶唑啉基烷基氧杂环丁烷的平滑开环，生成恶唑啉基烯丙基醇，这是被掩盖的Baylis-Hillman加合物，收率良好或优异。提出了一种E2-E1cb样的syn-beta消除方法，以解释所研究的肟基的易于碱促进的异构化。

  DOI：

  10.1021/jo026234d

文献信息

• Oxazolinyloxiranyllithium-Mediated Stereoselective Synthesis of α-Epoxy-β-amino Acids
  作者：Renzo Luisi、Vito Capriati、Leonardo Degennaro、Saverio Florio

  DOI：10.1021/ol034927q

  日期：2003.7.1

  [reaction: see text] The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazolidinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O

  [反应：见正文]通过将恶唑啉基亚氧烷基锂的化学与硝酮的化学相结合的途径描述了新型α-环氧-β-氨基酸的立体选择性合成。已分离出中间体三恶二氮杂二螺[2.0.4.3]十一烷4并通过水解转化为环氧-5-异恶唑烷酮5，该环氧-5-异恶唑烷酮5可通过NO还原转化为α-环氧-β-氨基酸8。
• Oxazolinyloxiranyllithium-mediated synthesis of highly strained heterocyclic compounds
  作者：Renzo Luisi、Vito Capriati、Leonardo Degennaro、Saverio Florio

  DOI：10.1016/j.tet.2003.09.017

  日期：2003.12

  The addition reaction of alpha-lithiated oxazolinyloxiranes to nitrones has been investigated. 1,5,9-Trioxa-8,10-diazadispiro[2.0.4.3]undecanes formed in a completely diastereoselective manner upon treatment of alpha-lithiated oxiranes with nitrones. The lithiation of optically active trans and cis-oxazolinyloxiranes followed by the addition of a nitrone resulted in the formation of the same dispirocyclic compound. An explanation for the observed stereoselectivity is provided. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of Allylic Alcohols from Oxazolinyloxiranes
  作者：Filippo M. Perna、Vito Capriati、Saverio Florio、Renzo Luisi

  DOI：10.1021/jo026234d

  日期：2002.11.1

  Lithium diisopropylamide (LDA) (or s-BuLi/TMEDA) in diethyl ether promotes smooth ring opening of oxazolinyl alkyl oxiranes to give oxazolinyl allylic alcohols, which are masked Baylis-Hillman adducts, in good to excellent yields. An E2-E1cb-like syn-beta-elimination is proposed to explain the easy base-promoted isomerization of the studied oxiranes.

  二乙醚中的二异丙基氨基化锂（LDA）（或s-BuLi / TMEDA）促进了恶唑啉基烷基氧杂环丁烷的平滑开环，生成恶唑啉基烯丙基醇，这是被掩盖的Baylis-Hillman加合物，收率良好或优异。提出了一种E2-E1cb样的syn-beta消除方法，以解释所研究的肟基的易于碱促进的异构化。
• Oxiranyllithium based synthesis of α-keto-2-oxazolines
  作者：Vito Capriati、Saverio Florio、Renzo Luisi、Vincenzo Russo、Antonio Salomone

  DOI：10.1016/s0040-4039(00)01558-6

  日期：2000.11

  alpha -Keto-2-oxazolines 5a-j have been efficiently prepared by lithiation [sec-(or n-)BuLi/TMEDA, Et2O, -100 degreesC] and rearrangement of oxiranyl oxazolines 2a-j. (C) 2000 Published by Elsevier Science Ltd.