4-(3-phenylisoxazol-5-yl)benzonitrile | 79182-05-1

• 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: 4-(3-phenylisoxazol-5-yl)benzonitrile
• 英文别名: 5-(4-cyanophenyl)-3-phenylisoxazole；3-phenyl-5-(4-cyanophenyl)-isoxazole；4-(3-Phenyl-1,2-oxazol-5-yl)benzonitrile
• CAS: 79182-05-1
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: WTLKWFCKLANCEC-UHFFFAOYSA-N

物化性质

• 沸点：
  463.1±33.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

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-(3-phenylisoxazol-5-yl)benzonitrile 在 盐酸 、 氨 作用下， 以 苯 为溶剂， 以40%的产率得到5-(4-Amidinophenyl)-3-phenylisoxazole
  参考文献：
  名称：

  Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

  摘要：

  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.

  DOI：

  10.1021/jm0612867
• 作为产物：
  描述：

  4-(3-phenylpropioloyl)benzonitrile 在 叠氮基三甲基硅烷 作用下， 以 三氯乙烯 为溶剂， 反应 12.0h， 以47%的产率得到4-(3-phenylisoxazol-5-yl)benzonitrile
  参考文献：
  名称：

  A direct access to isoxazoles from ynones using trimethylsilyl azide as amino surrogate under metal/catalyst free conditions

  摘要：

  描述了一种从易得的炔酮中使用三甲基硅基叠氮作为氨代用体，在异常简单的条件下获得异噁唑并具有出色的官能团兼容性的一般方法。

  DOI：

  10.1039/c6cc02047j

文献信息

• 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。
• <i>tert</i>-Butyl nitrite triggered radical cascade reaction for synthesizing isoxazoles by a one-pot multicomponent strategy
  作者：Leijing Chen、Zhen Wang、Hui Liu、Xinyue Li、Bin Wang

  DOI：10.1039/d2cc02823a

  日期：——

  TBN/Na₂S₂O₈-mediated radical cascade reaction of alkenes with aldehydes involving the formation of diverse new bonds in one-pot.

  TBN/Na2S2O8介导的烯烃与醛的自由基级联反应，涉及在一个反应体系中形成多种新键。
• 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。
• Electrochemical assembly of isoxazoles <i>via</i> a four-component domino reaction
  作者：Yuanyuan Zhao、Xinyue Li、Simon L. Homölle、Bin Wang、Lutz Ackermann

  DOI：10.1039/d3sc05946d

  日期：——

  Multicomponent domino reactions via electrochemical annulations have emerged as a robust strategy for the rapid assembly of heterocyclics. Herein, an electrochemical annulation via a [1 + 2 + 1 + 1] four-component domino reaction was accomplished in a user-friendly undivided cell setup to assemble valuable five-membered isoxazole motifs. Our approach is characterized by a high level functional group

  通过电化学环化的多组分多米诺骨牌反应已成为杂环化合物快速组装的稳健策略。在此，通过[1 + 2 + 1 + 1]四组分多米诺骨牌反应在用户友好的未分割的单元设置中完成电化学成环，以组装有价值的五元异恶唑基序。我们的方法的特点是高水平的官能团耐受性和操作简单性，避免了预功能化基材的繁琐且耗时的制备。进行了详细的机制研究，包​​括同位素标记、动力学研究、循环伏安法 (CV) 分析和中间表征，为自由基途径提供了支持。
• Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles
  作者：Jonathan E. Grob、Jill Nunez、Michael A. Dechantsreiter、Lawrence G. Hamann

  DOI：10.1021/jo201973t

  日期：2011.12.16

  The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki-Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MLDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki-Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.