4-(5-phenylisoxazol-3-yl)benzonitrile | 79182-02-8

• 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: 4-(5-phenylisoxazol-3-yl)benzonitrile
• 英文别名: 4-(5-Phenyl-1,2-oxazol-3-yl)benzonitrile
• CAS: 79182-02-8
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: MGWCYJVJQRSTBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-phenylisoxazol-3-yl)benzonitrile 在 silver(I) acetate 、 palladium diacetate 、 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 5-benzoyl-6-(4-cyanophenyl)nicotinate
  参考文献：
  名称：

  使用DMSO作为单碳替代物，在铜介导的吡啶合成中4-乙烯基异恶唑的异常反应性。

  摘要：

  已经开发了一种通过铜介导的异恶唑裂解合成烟酸酯衍生物和四取代吡啶的有效方案。这项工作的重点是在反应条件下观察到4-乙烯基异恶唑具有异常的反应活性。DMSO可作为单碳替代物，在反应过程中生成两个C–C键，从而生成一个活性亚甲基。该协议为密集取代的N杂环化合物的组装提供了一种便捷的方法。

  DOI：

  10.1021/acs.orglett.0c01935
• 作为产物：
  描述：

  4-氰基苯甲醛 在 oxone||potassium monopersulfate triple salt 、 potassium chloride 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 4-(5-phenylisoxazol-3-yl)benzonitrile
  参考文献：
  名称：

  异恶唑和钌介导的三取代吡咯的位置选择性C–H烯基化反应中的催化剂控制

  摘要：

  在确定异恶唑的CH链烯基化反应中的位置选择性方面，证明了高水平的催化剂控制能力。阳离子铑介导的强方向性基团在近端芳基环处促进C（sp 2）-H活化，而钯介导的亲电金属化作用则在该方向的远端位置导致C（sp 2）-H活化团体。通过钌和铜的共催化合成这种C–H链烯基化产物，可得到一种高效的方法，用于组装密集取代的吡咯。

  DOI：

  10.1021/acs.orglett.9b00446

文献信息

• Catalyst Control in Positional-Selective C–H Alkenylation of Isoxazoles and a Ruthenium-Mediated Assembly of Trisubstituted Pyrroles
  作者：Pravin Kumar、Manmohan Kapur

  DOI：10.1021/acs.orglett.9b00446

  日期：2019.4.5

  determining the positional selectivity in C–H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C–H alkenylation product via ruthenium and copper co-catalysis

  在确定异恶唑的CH链烯基化反应中的位置选择性方面，证明了高水平的催化剂控制能力。阳离子铑介导的强方向性基团在近端芳基环处促进C（sp 2）-H活化，而钯介导的亲电金属化作用则在该方向的远端位置导致C（sp 2）-H活化团体。通过钌和铜的共催化合成这种C–H链烯基化产物，可得到一种高效的方法，用于组装密集取代的吡咯。
• Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1719767A1

  公开（公告）日：2006-11-08

  Novel dicationic 3,5-diphenylisoxazole compounds are described. Synthetic routes to these novel compounds are provided. Several of the compounds displayed in vitro activity versus Trypanosoma brucei brucei and Plasmodium falciparum comparable to that of furamidine. A majority of the novel compounds also were less toxic to VERO cells than furamidine.

  描述了一种新型的双阳离子3,5-二苯基异噁唑化合物。提供了合成这些新型化合物的途径。其中几种化合物在体外显示出对布鲁氏锥虫和疟原虫的活性，与呋胺啶相当。大多数新型化合物对VERO细胞的毒性也比呋胺啶小。
• 4,5-Dihydro-1,2,4-oxadiazole as a Single Nitrogen Transfer Reagent: Synthesis of Functionalized Isoxazoles Assisted by Sc(OTf)₃ or Au(I)/Sc(OTf)₃ Synergistic Catalysis
  作者：Ali Wang、Peizhuo Lv、Yuanhong Liu

  DOI：10.1021/acs.orglett.3c01566

  日期：2023.6.16

  heterocycle, 4,5-dihydro-1,2,4-oxadiazole, was found to act as a single nitrogen atom transfer reagent via elimination of a ketone/aldehyde and a nitrile. This reagent was successfully applied for the synthesis of isoxazoles from ynones promoted by Sc(OTf)3 or through Au(I)/Sc(OTf)3 synergistic catalysis. The efficiency of this protocol was also demonstrated by its application in modifications of structurally

  五元 N–O 杂环 4,5-二氢-1,2,4-恶二唑被发现通过消除酮/醛和腈作为单氮原子转移试剂。该试剂已成功应用于由Sc(OTf) 3或Au(I)/Sc(OTf) 3协同催化促进的炔酮合成异恶唑。该协议的效率也通过其在结构复杂的天然产品和药物的修改中的应用得到证明。
• Gold‐Catalyzed Cyclization of Yndiamides with Isoxazoles via α‐Imino Gold Fischer Carbenes
  作者：Zixuan Tong、Philip J. Smith、Helena D. Pickford、Kirsten E. Christensen、Edward A. Anderson

  DOI：10.1002/chem.202302821

  日期：2023.12.14

  Gold-catalyzed [3+2] aminative cyclization of yndiamides and isoxazoles affords polysubstituted diaminopyrroles via the intermediacy of an α-imino gold Fischer carbene. The reaction proceeds rapidly under mild conditions; high regioselectivity was achieved via a subtle steric bias between the nitrogen substituents, as supported by DFT calculations. The reaction outcome could be switched to 1,4-oxazepines

  金催化的茚二酰胺和异恶唑的[3+2]氨基环化通过α-亚氨基金费歇尔卡宾提供多取代的二氨基吡咯。反应在温和条件下快速进行；正如 DFT 计算所支持的，高区域选择性是通过氮取代基之间微妙的空间偏差实现的。以苯并异恶唑为底物，反应产物可转化为 1,4-氧氮杂卓类化合物。
• Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles
  作者：Donald A. Patrick、Stanislav A. Bakunov、Svetlana M. Bakunova、E. V. K. Suresh Kumar、Richard J. Lombardy、Susan Kilgore Jones、Arlene S. Bridges、Oksana Zhirnov、James Edwin Hall、Tanja Wenzler、Reto Brun、Richard R. Tidwell

  DOI：10.1021/jm0612867

  日期：2007.5.1

  3,5-Bis(4-amidinophenyl)isoxazole (3)an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazoleand 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43 were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.