N-(cyanomethyl)-4-nitrobenzamide | 5555-32-8

• 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: N-(cyanomethyl)-4-nitrobenzamide
• 英文别名: N-(p-Nitro-benzoyl)-aminoacetonitril
• CAS: 5555-32-8
• 化学式: C₉H₇N₃O₃
• mdl: MFCD01212064
• 分子量: 205.173
• InChiKey: XSCPWDNADRIBGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  N-(cyanomethyl)-4-nitrobenzamide 在 盐酸 、 亚硝酸异丙酯 、 三氯氧磷 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 生成 5-(4-nitro-phenyl)-[1,2,4]oxadiazole-3-carbonitrile
  参考文献：
  名称：

  Brachwitz,H., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 447 - 454

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 氨基乙腈 在 sodium hydroxide 作用下， 生成 N-(cyanomethyl)-4-nitrobenzamide
  参考文献：
  名称：

  Syntheses of 2-Acylaminoacetamidine and 3-Acylaminopropionamidine Derivatives

  摘要：

  为了检测它们的抗病毒活性，通过相应的腈类经由乙基咪唑合成2-酰氨基乙脒（II）和3-酰氨基丙脒盐酸盐（III）。假设了乙基2-酰氨基乙咪唑和乙基3-酰氨基丙咪唑在酰胺化过程中的反应活性差异。通过参考相应的单氰单酯（ethyl p-(N-cyanoethylcarbamoyl) benzoate）（XXI）的红外光谱，讨论了二氰（对-氰基）苯甲酰胺丙腈（XVIII）的亚胺酯化。其中，3-（对-甲基）苯甲酰胺丙脒盐酸盐被发现对小鼠和膜培养中的流感病毒具有抑制作用。

  DOI：

  10.1248/cpb.16.2355

文献信息

• N-ACYLATED AMINO ACID IMINO CHLORIDES AND A QUALITATIVE STUDY OF RING CLOSURE AMONG N-ACYLAMINO ACID CHLORIDES
  作者：Edward Ronwin

  DOI：10.1139/v57-140

  日期：1957.9.1

  Products have been isolated from the treatment of N-acylaminoacetonitriles with dry hydrogen chloride which are either the open-chain imino acid chlorides or the dissociated salt forms. These compound types have often been postulated as reaction intermediates but never isolated with an unsubstituted nitrogen atom. In the unsubstituted condition they are analogous to regular or oxygen acid chlorides.Several N-acylamino acids were treated with PCl₅ and the reaction solutions were subjected to infrared spectral analyses. The results indicate that the open-chain acid chloride, rather than the azlactone salt, is the predominant product obtained with the compounds used in this investigation.

  产品已经从N-酰氨基乙腈与干氯化氢的处理中分离出来，这些产品是开链亚氨基酸氯化物或解离的盐形式。这些化合物类型经常被假设为反应中间体，但从未与未取代的氮原子分离出来。在未取代的条件下，它们类似于常规或氧酸氯化物。几种N-酰氨基酸被PCl5处理，反应溶液经过红外光谱分析。结果表明，在这项研究中使用的化合物中，开链酸氯化物而不是氮内酯盐是主要产物。
• Nickel‐Catalyzed Construction of 2,4‐Disubstituted Imidazoles <i>via</i> C–C Coupling and C−N Condensation Cascade Reactions
  作者：Shengyang Fang、Haihua Yu、Xicheng Yang、Jianqi Li、Liming Shao

  DOI：10.1002/adsc.201900096

  日期：2019.7.11

  A convenient Ni(II)‐catalyzed C−C and C−N cascade coupling reaction was developed to directly access various 2,4‐disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate‐to‐excellent yields. The tolerance of halogen and N‐containing heterocyclic groups demonstrates the versatility of this method for further synthetic explorations

  开发了一种方便的Ni（II）催化的C-C和C-N级联偶联反应，可直接使用各种2,4-二取代的咪唑。反应范围涵盖了各种芳基和脂肪族取代基，显示出中等至优异的收率。卤素和公差Ñ含杂环基团的演示此方法作进一步的合成探索的多功能性。
• Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles
  作者：SEIGO SUZUE、TUTOMU IRIKURA

  DOI：10.1248/cpb.16.1417

  日期：——

  For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.

  为了阐明贻贝症与四氯化碳诱导的大鼠肝脏坏死抑制之间的结构关系，合成了许多与氨基乙腈相关的化合物。N-氨基酰氨基乙腈（VIII，XIV）是从邻苯二甲酰氨基酰氨基乙腈合成的。VIII被转化为2-羟基亚胺-5-氧杂哌嗪衍生物（XV）和5-氧-2-硫杂哌嗪（XX）。还描述了N-(N-酰氨基酰)氨基乙腈的制备。此外，N-α-羟基酰氨基乙腈是由α-羟基酸的氯化物与氨基乙腈反应制备的。此外，通过用醋酸无水物处理，XV（R=H）被转化为2-乙酰氨基-5-乙酰氧基吡唑。
• Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
  作者：Ling Dai、Shuling Yu、Ningning Lv、Xuanzeng Ye、Yinlin Shao、Zhongyan Chen、Jiuxi Chen

  DOI：10.1021/acs.orglett.1c01762

  日期：2021.8.6

  efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical

  我们在此报告了一种以单步方式组装多取代咪唑和恶唑的有效方法。这些转化基于容易获得的芳香族羧酸和脂肪族腈的脱羧加成和环化，并表现出良好的官能团兼容性和高步骤经济性。该反应是可扩展的，制备的产品可以转化为实用的骨架。重要的是，莫罗替尼的后期衍生化突出了这种方法的潜在效用。
• N-cyanoalkyl-N-haloalkylthio carboxamides as fungicides
  申请人：Chevron Research Company

  公开号：US04785019A1

  公开（公告）日：1988-11-15

  N-cyanoalkyl-N-haloalkylthio alkyl-, aryl- and aralkyl-carboxamides of the general formula: ##STR1## wherein R is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 4 halogen atoms; lower alkoxyalkylene; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 16 carbon atoms; or substituted aryl or substituted aralkyl both substituted with 1 to 3 substituents independently selected from phenyl, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, halogen, nitro, cyano, ##STR2## wherein R.sup.4 is hydrogen or lower alkyl of 1 to 6 carbon atoms, ##STR3## wherein R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms; R.sup.1 and R.sup.2 are independently hydrogen, or lower alkyl of 1 to 6 carbon atoms; and R.sup.3 is alkyl of 1 to 3 carbon atoms substituted with 3 to 6 halogen atoms or trihalovinyl are fungicidal.

  通用公式为：##STR1## 其中R是1至10个碳原子的烷基，3至10个碳原子的环烷基，2至6个碳原子的低烯基或2至6个碳原子的低炔基，所有这些都可以选择性地用1至4个卤原子取代；低烷氧基烷基；6至12个碳原子的芳基；7至16个碳原子的芳基烷基；或取代的芳基或取代的芳基烷基，两者都取代为1至3个从苯基、1至6个碳原子的低烷基、1至6个碳原子的低烷氧基、1至6个碳原子的低烷硫基、卤素、硝基、氰基、##STR2## 其中R.sup.4是氢或1至6个碳原子的低烷基，##STR3## 其中R.sup.5和R.sup.6独立地是氢或1至6个碳原子的低烷基；R.sup.1和R.sup.2独立地是氢，或1至6个碳原子的低烷基；R.sup.3是1至3个碳原子的烷基，取代有3至6个卤素原子或三卤乙烯基，具有杀真菌作用。