5-phenyl-3-propyl-2-isoxazoline | 120802-95-1

• 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-propyl-2-isoxazoline
• 英文别名: Molofbltnwqftr-uhfffaoysa-；5-phenyl-3-propyl-4,5-dihydro-1,2-oxazole
• CAS: 120802-95-1
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: MOLOFBLTNWQFTR-UHFFFAOYSA-N

物化性质

• 沸点：
  285.2±43.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙烯 、 丁醛肟 在 Oxone 、 potassium iodide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以13%的产率得到5-phenyl-3-propyl-2-isoxazoline
  参考文献：
  名称：

  Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant

  摘要：

  异噁唑啉可以通过催化氧化环化反应，利用次碘酸盐媒介有效合成，反应从醛肟和烯烃出发，产率良好。此反应涉及从催化量的KI和Oxone原位生成的活性碘物种。

  DOI：

  10.1039/c3cc41164h

文献信息

• Hypervalent Iodine Catalyzed Generation of Nitrile Oxides from Oximes and their Cycloaddition with Alkenes or Alkynes
  作者：Akira Yoshimura、Kyle R. Middleton、Anthony D. Todora、Brent J. Kastern、Steven R. Koski、Andrey V. Maskaev、Viktor V. Zhdankin

  DOI：10.1021/ol401815n

  日期：2013.8.2

  Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution

  使用恶酮作为末端氧化剂，高价碘催化醛肟的氧化生成腈氧化物，该腈氧化物与烯烃和炔烃反应生成相应的异恶唑啉和异恶唑，产率中等至良好。该反应涉及在甲醇水溶液中在六氟异丙醇存在下由催化的碘芳烃和氧酮原位形成的活性高价碘物质。
• KF/Al₂O₃: Solid-Supported Reagent Used in 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide
  作者：Monalisa Boruah、Dilip Konwar

  DOI：10.1080/00397911.2011.558665

  日期：2012.11.15

  Abstract The stereoselective synthesis of 2-isoxazolidine through 1,3-dipolar cycloaddition reaction of nitrile oxide, which is in situ generation from aldoxime in the presence of N-bromosuccinamide and solid-supported reagent KF/Al2O3 at room temperature, is reported. KF/Al2O3 is sufficiently basic such that it can replace organic bases such as Et3N used in typical procedures and it catalyses the

  摘要 报道了在室温下，在 N-溴代琥珀酰胺和固载试剂 KF/Al2O3 存在下，由醛肟原位生成腈氧化物的 1,3-偶极环加成反应立体选择性合成 2-异恶唑烷。KF/Al2O3 具有足够的碱性，因此它可以替代典型程序中使用的有机碱，例如 Et3N，并且它催化反应以提高反应速率。图形概要
• A New Method for the Generation of Nitrile Oxides and Its Application to the Synthesis of 2-Isoxazolines
  作者：Alfred Hassner、K. M. Lokanatha Rai

  DOI：10.1055/s-1989-27152

  日期：——

  Reaction of aldoximes with choramine-T leads to formation of nitrile oxides which can react in situ intra- or intermolecularly with olefinic compounds to produce isoxazolines in good yield.

  醛肟与氯胺-T 反应会生成腈氧化物，腈氧化物可在分子内或分子间与烯烃化合物发生原位反应，从而以良好的收率生成异噁唑啉。
• Diffusion mixing with a volatile tertiary amine as a very efficient technique for 1,3-dipolar cycloaddition reactions proceeding <i>via</i> dehydrohalogenation of stable precursors of reactive dipoles
  作者：Dmitry E. Shybanov、Maria E. Filkina、Maxim E. Kukushkin、Yuri K. Grishin、Vitaly A. Roznyatovsky、Nikolai V. Zyk、Elena K. Beloglazkina

  DOI：10.1039/d2nj03756d

  日期：——

  result of tertiary amine vapor diffusion into the reaction mixture makes it possible to obtain the products of 1,3-dipolar cycloaddition reactions in high yields and without the side product formation due to the created conditions of “dipole starvation”. The proposed method of diffusion reagent mixing allows us to carry out 1,3-dipolar cycloaddition reactions with low-stability and easily dimerizing nitrile

  挥发性试剂蒸气自发扩散到含有不稳定反应中间体的稳定前体的溶液中，可能是进行某些有机反应（包括 1,3-偶极环加成）的最简单方法。在目前的工作中，该技术用于生成腈亚胺和腈氧化物，用于随后通过挥发性叔胺（Et 3 N和 Me 3N 或 DIPEA)。由于叔胺蒸气扩散到反应混合物中产生高反应性中间体，因此可以以高产率获得 1,3-偶极环加成反应的产物，并且不会由于“偶极饥饿”的创造条件而形成副产物”。所提出的扩散试剂混合方法使我们能够以低稳定性进行 1,3-偶极环加成反应，并且容易以高收率二聚化腈氧化物和腈亚胺，并且在实验上非常容易。事实上，1,3-偶极子是通过这种“逐个分子”的方法获得的，从而防止了它们不需要的二聚化。
• Synthesis of Hydroximoyl Chlorides from Aldoximes and Benzyltrimethylammonium Tetrachloroiodate (BTMA ICl4)
  作者：Shuji Kanemasa、Haruhiko Matsuda、Akio Kamimura、Takaaki Kakinami

  DOI：10.1016/s0040-4020(99)01047-9

  日期：2000.2

  Benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) acts as a convenient reagent to convert aldoximes to hydroximoyl chlorides by a simple procedure. When an aldoxime is treated with BTMA ICl4 in dichloromethane, the suspension of BTMA ICl4 shortly diasappears as the reaction proceeds. The resulting BTMA ICl2 can he precipitated out by adding diethyl ether. Not only stable aromatic and heteroaromatic hydroximoyl chlorides can be isolated by this method but also rather unstable aliphatic hydroximoyl chlorides can be generated in situ. 1,3-Dipole trapping with a dipolarophile is performed in one flask and in some cases the chlorination is successfully performed in the presence of dipolarophile and triethylamine. Effect of MS 4A has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

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