3-乙酰基-4-氨基苯甲腈 | 56079-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰基-4-氨基苯甲腈
• 英文名称: 3-acetyl-4-aminobenzonitrile
• CAS: 56079-07-3
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: NWFYRBPLXDMNRN-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133.5 °C
• 沸点：
  341.0±32.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-乙酰基-4-氨基苯甲腈 在 sodium azide 、 硫酸 、 水 、 sodium nitrite 作用下， 反应 6.33h， 生成 3-Methylbenzo[c]isoxazole-5-carbonitrile
  参考文献：
  名称：

  Substituent Effects on the Lifetimes and Reactivities of Arylnitrenium Ions Studied by Laser Flash Photolysis and Photothermal Beam Deflection

  摘要：

  Photolysis of 5-substituted-N-tert-butyl-3-methylanthranilium produces transient N-tert-butyl-(2-acetyl-4-substituted) phenylnitrenium ions. This is confirmed by identification of the stable products, transient absorption experiments, and photothermal beam deflection experiments. Analysis of the stable photoproducts shows that the major decay pathway for these species is addition of nucleophiles to the aromatic ring. The kinetics of the these reactions were examined with the goal of determining how various ring substituents affect arylnitrenium ion stability. Rate constants measured for the 4-phenyl and 4-methoxy derivatives are compared with those from previous work. It is shown that a 4-phenyl group stabilizes the nitrenium ion to approximately the same extent as a 4-methoxy group. Both of these substituents stabilize the arylnitrenium ions considerably more than 4-halogens or a 4-methyl group. Time resolved photothermal beam deflection experiments were applied to the 4-cyano and 4-unsubstituted derivatives, which gave no transient absorption spectra. The latter two compounds are shown to have lifetimes of less than 100 ns.

  DOI：

  10.1021/ja961518z
• 作为产物：
  描述：

  3-乙酰胺基苯乙酮 在 盐酸 、 硫酸 、 硝酸 、 铁粉 、 溶剂黄146 、 copper(l) chloride 作用下， 生成 3-乙酰基-4-氨基苯甲腈
  参考文献：
  名称：

  Simpson et al., Journal of the Chemical Society, 1945, p. 646,655

  摘要：

  DOI：

文献信息

• Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles
  作者：Nicholas P. Massaro、Aayushi Chatterji、Indrajeet Sharma

  DOI：10.1021/acs.joc.9b01906

  日期：2019.11.1

  pyridine-stabilized ketenimine zwitterionic salts, which are prepared through click chemistry from readily accessible alkynes and sulfonyl azides. To demonstrate their synonymous reactivity to ketenimines, these salts have been utilized in a cascade sequence to access highly functionalized quinolines including the core structures of an antiprotozoal agent and the potent topoisomerase inhibitor Tas-103.

  酮基亚胺是通用的合成中间体，能够在有机合成中进行新颖的转化。由于它们固有的不稳定性和高水平的反应性，它们通常在原位产生。在这里，我们报告吡啶稳定的酮亚胺两性离子盐，其是通过点击化学从易于获得的炔烃和磺酰叠氮化物制备的。为了证明它们与酮亚胺的同义反应性，已将这些盐以级联顺序用于访问高度功能化的喹啉，包括抗原生动物药和强效拓扑异构酶抑制剂Tas-103的核心结构。
• Auto-Tandem Catalysis: Synthesis of Acridines by Pd-Catalyzed C=C Bond Formation and C(<i>sp²</i>)-N Cross-Coupling
  作者：Zhongxing Huang、Yang Yang、Qing Xiao、Yan Zhang、Jianbo Wang

  DOI：10.1002/ejoc.201201070

  日期：2012.10.10

  A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C–N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized

  通过连续的C=C双键形成和C-N交叉偶联实现了钯催化合成吖啶的简便方法。各种功能化的吖啶可以通过简单的操作从容易获得的邻二卤代苯和 N-甲苯磺酰腙中获得。这种一锅法在两个耦合伙伴方面具有广泛的范围，并为功能化吖啶衍生物提供了一种有效的途径，这些衍生物通常难以通过以前已知的方法合成。
• Photo-Fries rearrangement of aryl acetamides: regioselectivity induced by the aqueous micellar green environment
  作者：Daniela Iguchi、Rosa Erra-Balsells、Sergio M. Bonesi

  DOI：10.1039/c5pp00349k

  日期：2016.1

  isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and

  光化学反应往往会产生一种以上的光产物。但是，如果可以在区域选择性条件下进行反应，生成单个光产物，则这种反应可能是强大的合成工具。在这种情况下，可以将水表面活性剂溶液用作反应介质，因为它们显示的产品与各向同性溶液的产品具有不同的功能。在这里，我们描述了通过研究对原型光反应的影响而获得的结果，这种反应被称为表面活性剂胶束（离子和非离子胶束）中几种取代的乙酰苯胺和α-萘乙酰胺的光-弗里斯反应。该反应涉及CN键的均质裂解以产生单线自由基对。表面活性剂胶束控制自由基对的旋转和平移性，
• Rh(<scp>iii</scp>)-catalyzed alkynylation: synthesis of functionalized quinolines from aminohydrazones
  作者：Pradeep Kumar、Vineeta Garg、Manoj Kumar、Akhilesh K. Verma

  DOI：10.1039/c9cc06205j

  日期：——

  terminal alkynes has been described. The reaction is oxidant/base-free and tolerates a wide variety of functional groups and has been successfully extended with 1,3 and 1,4-bis(phenylethynyl)benzenes to afford 1,3- and 1,4-bis(4-methylquinolin-2-yl)benzenes and 2-(3/4-ethynylphenyl)-4-methylquinolines. Furthermore, the control experiment supports the proposed reaction mechanism.

  已经描述了使用2-氨基hydr和末端炔烃的铑催化的，化学和区域选择性的功能化喹啉的合成。该反应不含氧化剂/碱，可耐受多种官能团，并已成功地与1,3和1,4-双（苯基乙炔基）苯反应，得到1,3-和1,4-双（4-）甲基喹啉-2-基）苯和2-（3 / 4-乙炔基苯基）-4-甲基喹啉。此外，对照实验支持所提出的反应机理。
• A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines
  作者：Kiran Chinthapally、Nicholas P. Massaro、Haylee L. Padgett、Indrajeet Sharma

  DOI：10.1039/c7cc07181g

  日期：——

  A serendipitous five-step cascade of rhodium vinylcarbenoids with aminochalcones enables a unique synthetic approach to highly functionalized tri- and tetra-cyclic quinolines. The cascade reaction begins with the insertion of aminochalcone nitrogen into rhodium vinylcarbenoids followed by intramolecular aldol cyclization to provide a substituted indoline intermediate that undergoes an oxy-Cope rearrangement

  铑乙烯基类胡萝卜素与氨基查耳酮的偶然五步级联使得独特的合成方法可用于高度官能化的三环和四环喹啉。级联反应开始于将氨基查耳酮氮插入乙烯基乙烯基类化合物铑中，然后进行分子内羟醛环化，以提供取代的二氢吲哚中间体，该中间体进行oxy-Cope重排以提供9元氮杂环，然后再通过分子内羟醛重排至官能化的喹啉/脱水顺序。在低至0.1 mol％的催化剂负载量下，级联反应已被证明适用于一系列氨基查耳酮和乙烯基类胡萝卜素。