2-(4-Nitrobenzamido)benzonitrile | 153172-75-9

• 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: 2-(4-Nitrobenzamido)benzonitrile
• 英文别名: N-(2-cyanophenyl)-4-nitrobenzamide；N-(2-Cyan-phenyl)-4-nitro-benzamid；Cambridge id 5134745
• CAS: 153172-75-9
• 化学式: C₁₄H₉N₃O₃
• 分子量: 267.244
• InChiKey: CXIUQNYZBOKINB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Nitrobenzamido)benzonitrile 在 盐酸 作用下， 生成 2-[(4-硝基苯甲酰基)氨基]苯甲酰胺
  参考文献：
  名称：

  Mechanism of Alkaline Cyclization of 2-(Substituted benzamido)benzamides to 4-Quinazolinones

  摘要：

  The title amides cyclize rapidly to the corresponding quinazolin-4-ones in aqueous alkaline solution at 25 degrees C; the pseudo-first-order rate constants fit the empirical equation k(obs) = k(max) [OH-]/K-m + [OH-] + [OH-]K-2(m')) where K-m' is essentially zero for all except the 4-nitro species. The value of K-m measures the ionization of the neutral amide 1 to nonproductive conjugate base 2. Studies of the cyclization in alkali of 2-benzamido-N-methylbenzamide (1i) and 2-(N-methylbenzamido)benzamide (1j) indicate that 7 carries over 99% of the reaction flux and that the tautomer 8 does not contribute significantly. The ratio k(max)/K-m, is a composite rate constant first order in 1 and first order in [OH-]. The value of the Hammett rho for k(max)/K-m (0.67) is consistent with the above scheme where decomposition of 7 is rate limiting.

  DOI：

  10.1021/jo00100a026
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 2-氨基苯甲腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以26%的产率得到2-(4-Nitrobenzamido)benzonitrile
  参考文献：
  名称：

  铜催化的邻氰基苯胺与高价碘鎓盐的氧化环封闭：氨基苯并恶嗪的芳基环封闭方法

  摘要：

  AbstractA novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho‐cyanoanilides and diaryliodonium triflates via an oxidative arylation–cyclization path. The reaction is supposed to involve the formation of highly active aryl‐copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2‐dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2–16 h.magnified image

  DOI：

  10.1002/adsc.201400763

文献信息

• Pd-Catalyzed tandem reaction of <i>N</i>-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
  作者：Jianghe Zhu、Yinlin Shao、Kun Hu、Linjun Qi、Tianxing Cheng、Jiuxi Chen

  DOI：10.1039/c8ob02421a

  日期：——

  The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, halogen and hydroxyl substituents, which are amenable for further synthetic elaborations, are well tolerated. Moreover, the present synthetic route

  已经开发了通过钯催化的芳基硼酸与N-（2-氰基芳基）苯甲酰胺的反应合成2,4-二取代的喹唑啉，其产率中等至优异。该方法显示出良好的官能团耐受性。特别是，对于进一步的合成修饰而言，卤素和羟基取代基是很好的耐受性。而且，本合成路线可以容易地按比例放大至克量而没有困难。该机制可能涉及亲核加成腈功能，形成亚胺中间体，然后分子内加成酰胺并脱水成喹唑啉环。
• Smyth, Richard M.; Williams, Andrew, Journal of the Chemical Society. Perkin transactions II, 1993, # 11, p. 2171 - 2174
  作者：Smyth, Richard M.、Williams, Andrew

  DOI：——

  日期：——
• Copper-Catalyzed Oxidative Ring Closure of<i>ortho</i>-Cyanoanilides with Hypervalent Iodonium Salts: Arylation-Ring Closure Approach to Iminobenzoxazines
  作者：Klára Aradi、Zoltán Novák

  DOI：10.1002/adsc.201400763

  日期：2015.2.9

  AbstractA novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho‐cyanoanilides and diaryliodonium triflates via an oxidative arylation–cyclization path. The reaction is supposed to involve the formation of highly active aryl‐copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2‐dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2–16 h.magnified image
• Mechanism of Alkaline Cyclization of 2-(Substituted benzamido)benzamides to 4-Quinazolinones
  作者：Barry Gardner、Angeline J. S. Kanagasooriam、Richard M. Smyth、Andrew Williams

  DOI：10.1021/jo00100a026

  日期：1994.10

  The title amides cyclize rapidly to the corresponding quinazolin-4-ones in aqueous alkaline solution at 25 degrees C; the pseudo-first-order rate constants fit the empirical equation k(obs) = k(max) [OH-]/K-m + [OH-] + [OH-]K-2(m')) where K-m' is essentially zero for all except the 4-nitro species. The value of K-m measures the ionization of the neutral amide 1 to nonproductive conjugate base 2. Studies of the cyclization in alkali of 2-benzamido-N-methylbenzamide (1i) and 2-(N-methylbenzamido)benzamide (1j) indicate that 7 carries over 99% of the reaction flux and that the tautomer 8 does not contribute significantly. The ratio k(max)/K-m, is a composite rate constant first order in 1 and first order in [OH-]. The value of the Hammett rho for k(max)/K-m (0.67) is consistent with the above scheme where decomposition of 7 is rate limiting.