5-phenyl-3-ethyl-Δ²-isoxazoline | 55134-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-phenyl-3-ethyl-Δ²-isoxazoline
• 英文别名: 3-Ethyl-5-phenyl-2-isoxazolin；3-ethyl-5-phenyl-4,5-dihydro-isoxazole；3-Ethyl-5-phenyl-Δ²-isoxazolin；3-Aethyl-5-phenyl-Δ2-isoxazolin；3-Ethyl-5-phenyl-4,5-dihydroisoxazole；3-ethyl-5-phenyl-4,5-dihydro-1,2-oxazole
• CAS: 55134-83-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: ZHHOTMLQQIDFAL-UHFFFAOYSA-N

物化性质

• 沸点：
  135-137 °C(Press: 5 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-ethyl-Δ²-isoxazoline 生成 (1E)-1-phenylpent-1-en-3-one
  参考文献：
  名称：

  Grund, Hartmut; Jaeger, Volker, Liebigs Annalen der Chemie, 1980, # 1, p. 80 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  3-ethyl-5-phenyl-2-trimethylsilanyloxy-isoxazolidine 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 5-phenyl-3-ethyl-Δ²-isoxazoline
  参考文献：
  名称：

  Torssell,K.; Zeuthen,O., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 118 - 124

  摘要：

  DOI：

文献信息

• A Convenient Preparative Method of Nitrile Oxides by the Dehydration of Primary Nitro Compounds with Ethyl Chloroformate or Benzenesulfonyl Chloride in the Presence of Triethylamine
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Hiroshi Shibafuchi、Kazuhiro Teramura

  DOI：10.1246/bcsj.59.2827

  日期：1986.9

  nitrile oxides (MeOCOC≡N→O, PhC≡N→O, and EtC≡N→O) were effectively generated in situ by dehydration of the corresponding primary nitro compounds (RCH2NO2) with PhSO2Cl or ClCOOEt in the presence of triethylamine. Various cycloadducts were prepared by the reaction of them with dipolarophiles. Some advantages of these methods are described in comparison with other known methods.

  在三乙胺的存在下，通过用 PhSO2Cl 或 ClCOOEt 使相应的初级硝基化合物 (RCH2NO2) 脱水，原位有效地生成了三种腈氧化物（MeOCOC≡N→O、PhC≡N→O 和 EtC≡N→O）。各种环加合物是通过它们与偶极试剂反应制备的。与其他已知方法相比，描述了这些方法的一些优点。
• An Improved Method for Preparation of Nitrile Oxides from Nitroalkanes for In Situ Dipolar Cycloadditions
  作者：Yochai Basel、Alfred Hassner

  DOI：10.1055/s-1997-1181

  日期：1997.3

  A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethyl-aminopyridine (3) as catalyst in the presence of dipolarophiles at room temperature afforded cycloadducts (e.g. 5,6, and 7) in improved yields compared to known methods. Solvent effects were also noted.

  已发现一种新方法，可以在温和条件下从硝基烷烃原位生成腈氧化物。因此，将硝基烷烃1与二叔丁基二羧酸酯（2）和含有催化剂的4-二甲基氨基吡啶（3）在室温下与极性偶极体反应，得到了环加成产物（例如5、6和7），其产率相比已知方法有了改善。同时也观察到了溶剂效应。
• 4,5-Dihydroisoxazoles by Copper(II)-Catalysed Condensation of Primary Nitroalkanes with Dipolarophiles
  作者：Francesco De Sarlo、Fabrizio Machetti、Luca Cecchi

  DOI：10.1055/s-2007-986629

  日期：2007.9

  Primary aliphatic nitro compounds condense with substituted alkenes to give 4,5-dihydroisoxazoles under copper(II) acetate catalysis in the presence of tertiary amines. Apparently nitrile ­oxides are not intermediates, as no furoxans are detected in these ­reactions.

  初级脂肪醇硝基化合物在铜(II)醋酸盐催化下与取代烯烃缩合生成4,5-二氢异噁唑，反应中存在第三胺。显然，腈氧化物并不是中间体，因为在这些反应中未检测到呋喃氧化物。
• Oxidation of isoxazolines by peracids - a useful route to β-hydroxy ketones and acylated diols
  作者：Pyeong-uk Park、Alan P. Kozikowski

  DOI：10.1016/s0040-4039(00)82433-8

  日期：——

  A method for bringing about the ring cleavage of isoxazolines by the use of peracids is described.

  描述了通过使用过酸引起异恶唑啉环裂解的方法。
• Synthesis of streptazolin: use of the aza-Ferrier reaction in conjunction with the INOC process to deliver a unique but sensitive natural product
  作者：Alan P. Kozikowski、Pyeong Uk Park

  DOI：10.1021/jo00302a036

  日期：1990.7