4-氰基重氮苯四氟硼酸盐 | 2252-32-6

• 中文名称: 4-氰基重氮苯四氟硼酸盐
• 英文名称: cyano derivative of benzenediazonium tetrafluoroborate
• 英文别名: 4-cyanophenyldiazonium tetrafluoroborate；4-carbonitrilebenzenediazonium tetrafluoroborate；p-cyanophenyltetrafluoroborate diazonium salt；4-cyano-benzenediazonium tetrafluoroborate；4-cyanobenzene diazonium tetrafluoroborate；4-cyanobenzenediazonium tetrafluoroborate
• CAS: 2252-32-6
• 化学式: BF₄*C₇H₄N₃
• 分子量: 216.933
• InChiKey: PHYIHPYMVWPPEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  4-氰基重氮苯四氟硼酸盐 在 chloro[1,3-bis(2,6-diisopropylphenyl)-2,4-diphenyl-imidazol-5-ylidene]copper(I) 、 盐酸羟胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 4-(5-chloro-4-phenyl-1H-1,2,3-triazol-1-yl)benzonitrile
  参考文献：
  名称：

  1,4-二取代-5-卤代-1,2,3-三唑的一般合成方法

  摘要：

  已开发出 1,4-二取代-5-卤代-1,2,3-三唑的一般合成方法。一锅两步法包括由 (aNHC)CuCl 催化的乙炔铜 (I) CuAAC 和有机叠氮化物，然后使用 NCS、NBS 或 I2 进行卤化。

  DOI：

  10.1002/ejoc.201700925
• 作为产物：
  描述：

  在 亚硝酸特丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 4-氰基重氮苯四氟硼酸盐
  参考文献：
  名称：

  Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC₅₀ (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

  DOI：

  10.1016/j.ejmech.2020.112703

文献信息

• A Selective and Benign Synthesis of Functionalized Benzalacetones <i>via</i> Mizoroki–Heck Reaction Using Aryldiazonium Salts
  作者：Therese Stern、Sven Rückbrod、Constantin Czekelius、Constanze Donner、Heiko Brunner

  DOI：10.1002/adsc.200900868

  日期：2010.10.9

  Palladium-catalyzed Mizoroki–Heck reactions were carried out in the presence of calcium carbonate in alcoholic solvents. Under these conditions an efficient preparation of functionalized benzalacetones was developed. The reactions were carried out at room temperature and aerobic conditions, giving the products within several minutes in up to 95% isolated yields. Furthermore, some kinetic investigations

  钯催化的Mizoroki-Heck反应是在碳酸钙存在下于醇类溶剂中进行的。在这些条件下，开发了一种高效制备功能化苯并丙酮的方法。反应在室温和有氧条件下进行，数分钟内获得产物，分离产率高达95％。此外，还介绍了一些动力学研究，机理见解和注意事项。
• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• A general electrochemical strategy for the Sandmeyer reaction
  作者：Qianyi Liu、Beiqi Sun、Zheng Liu、Yi Kao、Bo-Wei Dong、Shang-Da Jiang、Feng Li、Guoquan Liu、Yang Yang、Fanyang Mo

  DOI：10.1039/c8sc03346c

  日期：——

  Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot

  本文中，我们报告了桑德迈尔反应的一般电化学策略。使用电作为驱动力，该协议采用一种简单且廉价的卤素源，例如NBS，CBrCl 3，CH 2 I 2，CCl 4，LiCl和NaBr进行芳基重氮盐的卤化。另外，我们发现这些电化学反应可以以一锅的方式使用苯胺作为起始原料来进行。此外，该方法的实用性在使用非常便宜的石墨作为电极的多克规模的芳基卤化物的合成中得到了证明。已经进行了一系列详细的机理研究，包括自由基时钟和自由基清除剂研究，循环伏安分析和原位电子顺磁共振（EPR）分析。
• Sandmeyer reactions. Part 7.1 An investigation into the reduction steps of Sandmeyer hydroxylation and chlorination reactions
  作者：Peter Hanson、Jason R. Jones、Alec B. Taylor、Paul H. Walton、Allan W. Timms

  DOI：10.1039/b200748g

  日期：2002.5.22

  aqueous solution, the reduction steps have been investigated by means of correlation analyses of the effects of diazonium ion substitution on the rates of reduction. For simple hydroxylation, a change of behaviour between diazonium ions substituted by electron donor groups and those substituted by electron acceptor groups is interpreted as a change within an inner-sphere process from rate-determining electron

  对于桑德迈尔水溶液中的羟基化和氯化反应，通过相关分析重氮离子取代对还原速率的影响，研究了还原步骤。对于简单的羟基化，被电子给体基团取代的重氮离子与被电子受体基团取代的重氮离子之间的行为变化被解释为内球过程中从速率确定电子转移到反应物速率确定缔合的变化。相比之下，对于柠檬酸盐促进的羟基化，类似的行为变化可解释为内层和外层电子转移之间的变化。对于氯化作用，在所检查的取代基范围内没有机理上的变化，但其行为方式与内球机理一致。根据重氮离子取代和催化剂连接对各种反应性氧化还原对的还原电势和自交换速率的影响，合理化了各种行为方式。重氮离子的还原反应和其他亲电反应的比较相关性分析用于支持关于Sandmeyer还原步骤的高级论证。建议铜我还原剂反应经由亲核桥连配体的重氮Ñ β以得到瞬变ž-adducts其为前体配合物和活化用于电子转移包括关于N-N键的旋转。
• Fischer Indole Synthesis with Organozinc Reagents
  作者：Benjamin A. Haag、Zhi-Guang Zhang、Jin-Shan Li、Paul Knochel

  DOI：10.1002/anie.201005319

  日期：2010.12.3

  Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]‐sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

  经典更新：烷基锌一级和二级试剂添加到各种芳基重氮盐中，通过[3,3]-σ移移和随后的芳构化作用，选择性地导致多官能吲哚。Fischer吲哚合成的这种有机金属变化可耐受各种官能团，并显示出绝对的区域选择性。