3-乙基-5-苯基-1,2-恶唑 | 4211-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-乙基-5-苯基-1,2-恶唑
• 英文名称: 3-ethyl-5-phenylisoxazole
• 英文别名: 3-ethyl-5-phenyl-isoxazole；3-Aethyl-5-phenyl-isoxazol；3-Ethyl-5-phenyl-isoxazol；3-ethyl-5-phenyl-1,2-oxazole
• CAS: 4211-90-9
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: ZGLWUJVEEZGKDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙基-5-苯基-1,2-恶唑 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 以95%的产率得到3-ethyl-4-iodo-5-phenylisoxazole
  参考文献：
  名称：

  炔丙胺通过一锅氧化/环化序列合成异恶唑

  摘要：

  已经有效地开发了一种合成异恶唑的简便策略，该策略包括将炔丙基胺氧化成相应的肟，然后由 CuCl 介导的后者分子内环化。该协议显示了一种构建一系列具有广泛官能团兼容性的异恶唑核心的简单方法。同时，可以成功进行克级实验和合成应用。

  DOI：

  10.1021/acs.joc.2c00896
• 作为产物：
  描述：

  methoxy-dimethyl(phenylethynyl)silane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex copper diacetate 、 异氰酸苯酯 、 三乙胺 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 3-乙基-5-苯基-1,2-恶唑
  参考文献：
  名称：

  Synthesis of 3,4,5-Trisubstituted Isoxazoles via Sequential [3 + 2] Cycloaddition/Silicon-Based Cross-Coupling Reactions

  摘要：

  A [3 + 2] cycloaddition reaction between alkynyldimethylsilyl ethers and arlyl and alkyl nitrile oxides to produce isoxazolylsilanols has been developed. The cross-coupling reactions of these heterocyclic silanols with a variety of aryl iodides affords 3,4,5 -trisubstituted isoxazoles. This sequential process allows for rapid variation of substituents at the 3 4, and 5 positions of the isoxazole.

  DOI：

  10.1021/jo047755z

文献信息

• One-Pot Copper(I)-Catalyzed Synthesis of 3,5-Disubstituted Isoxazoles
  作者：Trond V. Hansen、Peng Wu、Valery V. Fokin

  DOI：10.1021/jo050163b

  日期：2005.9.1

  3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used

  通过便利的一锅三步程序，利用原位生成的腈氧化物和末端乙炔之间的区域选择性铜（I）催化的环加成反应，以方便的一锅三步程序以高收率获得了3,5-二取代的异恶唑。大多数官能团不干扰反应，该反应可以在水性溶剂中进行而无需氧气的保护。由于所有试剂都以化学计量的形式使用，因此副产物的形成得以最小化。
• Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of <i>N</i>-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles
  作者：Xiaoqiang Lei、Longbo Li、Yu-Peng He、Yefeng Tang

  DOI：10.1021/acs.orglett.5b02570

  日期：2015.11.6

  A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative

  N-磺酰基-1,2,3-三唑与异恶唑的新型铑（II）催化的正式[3 + 2]环加成反应已为合成多取代的3-氨基吡咯衍生物提供了一种有效的方法。还开发了一种操作简单的一锅式合成方法，可从末端炔烃，甲苯磺酰基叠氮化物和异恶唑合成标题化合物。提出的反应提供了在相关的环加成反应中使用1,2,3-三唑作为[2C]-组分的说明性实例。
• 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。
• An Efficient, Scaleable Procedure for the Conversion of Esters to Isoxazoles
  作者：W. H. Bunnelle、P. R. Singam、B. A. Narayanan、C. W. Bradshaw、J. S. Liou

  DOI：10.1055/s-1997-1211

  日期：1997.4

  A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.

  已开发出一种简明的区域选择性合成异噁唑的路线，该方法基于酯与金属化亚胺的缩合。中间体连氨酰胺与羟胺反应顺利，经过脱水后，生成取代的异噁唑。该方法已用于ABT-418的多千克规模制备，ABT-418是一种新型的胆碱能通道激活剂。