N-(cyanomethyl)-4-methylbenzamide | 22198-21-6

• 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-methylbenzamide
• 英文别名: N-p-toluoyl-glycine nitrile；N-p-Toluoyl-glycin-nitril；p-Tolursaeure-nitril；2-(p-Methyl-benzoyl-amino)-acetonitril
• CAS: 22198-21-6
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD00548034
• 分子量: 174.202
• InChiKey: MIDDMBTVJHCISN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(cyanomethyl)-4-methylbenzamide 在 盐酸 、 氢氧化钾 作用下， 生成 4-甲基马尿酸
  参考文献：
  名称：

  Klages; Haack, Chemische Berichte, 1903, vol. 36, p. 1648

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯甲酰氯 在 sodium hydroxide 、 苯 作用下， 生成 N-(cyanomethyl)-4-methylbenzamide
  参考文献：
  名称：

  Klages; Haack, Chemische Berichte, 1903, vol. 36, p. 1648

  摘要：

  DOI：

文献信息

• Syntheses of 2-Acylaminoacetamidine and 3-Acylaminopropionamidine Derivatives
  作者：TAKEO UEDA、YOSHIHISA OKAMOTO、TADAKAZU TSUJI、MASAKO MURAOKA

  DOI：10.1248/cpb.16.2355

  日期：——

  For the purpose to examine as to their antiviral activities, 2-acylaminoacetamidine (II) and 3-acylaminopropionamidine hydrochlorides (III) were synthesized from the corresponding nitriles via ethyl imidates. The difference of the reactivity between ethyl 2-acylaminoacetimidates and ethyl 3-acylaminopropionimidates on the course of amidination were postulated. Iminoesterification of dinitrile, (p-cyano) benzamidopropionitrile (XVIII), was discussed by referring the infrared spectrum of a corresponding monocyanomonoester, ethyl p-(N-cyanoethylcarbamoyl) benzoate (XXI). Among the compounds obtained hereof, 3-(p-methyl) benzamidopropionamidine hydrochloride was found to have an inhibitory effect on influenza virus in mice and in membrane culture.

  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。
• 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。
• HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS
  申请人：Babu Yarlagadda S.

  公开号：US20120309773A1

  公开（公告）日：2012-12-06

  The invention provides compounds of formula I: or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula I.

  本发明提供公式I的化合物：或其盐，如本文所述。本发明还提供包含公式I化合物的药物组合物，制备公式I化合物的方法，用于抑制免疫反应或治疗癌症或血液恶性肿瘤的治疗方法，使用公式I化合物的中间体有助于制备公式I化合物。
• Preparation of substituted benzamides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0135304A2

  公开（公告）日：1985-03-27

  Benzamides of the formula (I): in which Ar is optionally substituted aryl; X is 0, S or NH and R is optionally substituted alkyl or alkenyl when X is 0 or S, or is optionally substituted alkenoyl when X is NH, are prepared by (a) reacting a compound of the formula (II): with a brominating agent in a solvent which is substantially chemically inert to the reactants and in which compound (II) is soluble, to form a compound of the formula (III): and (b) reacting the compound (III) with a compound RXH. Preferably, bromination is carried out rapidly in dried ethyl acetate. The process avoids hydration of the CN group of the compound (III) to a carbamoyl group obviating a subsequent dehydration step later. The intermediate compound (III) is novel. The substituted benzamides are useful as herbicides and fungicides.

  式(I)的苯甲酰胺： 其中 Ar 是任选取代的芳基；X 是 0、S 或 NH；当 X 是 0 或 S 时，R 是任选取代的烷基或烯基，或当 X 是 NH 时，R 是任选取代的烯酰基。 (a) 将式 (II) 的化合物 与溴化剂在对反应物基本化学惰性且化合物 (II) 可溶解的溶剂中反应，生成式 (III) 的化合物： 和 (b) 使化合物 (III) 与化合物 RXH 反应。溴化反应最好在干燥的乙酸乙酯中快速进行。 该工艺避免了化合物（III）的 CN 基团水合成为氨基甲酰基，从而省去了随后的脱水步骤。 中间体化合物 (III) 是一种新型化合物。 取代的苯甲酰胺可用作除草剂和杀真菌剂。
• Preparation of bromoacetamides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0144177A1

  公开（公告）日：1985-06-12

  Bromoacetamides of the formula ArCONHCH(Br)CONH2 are obtained by addition to bromine of a solution of ArCONHCH2CN in a saturated aliphatic carboxylic acid preferably glacial acetic or propionic acid. This is an improvement in a process described in European Patent Specification No. 0059536 in which the bromine is added to a solution of the cyanomethylbenzamide, enabling consistently high yields (e.g. 75 to 90%) to be obtained.

  通过将 ArCONHCH2CN 在饱和脂肪族羧酸（最好是冰醋酸或丙酸）中的溶液加入溴，可获得式为 ArCONHCH(Br)CONH2 的溴乙酰胺。这是对欧洲专利说明书第 0059536 号中描述的工艺的改进，在该工艺中，溴被添加到氰甲基苯甲酰胺的溶液中，从而能够获得稳定的高产率（例如 75% 至 90%）。