N-(氰基甲基)-苯甲酰胺 | 5692-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(氰基甲基)-苯甲酰胺
• 英文名称: 2-benzamido-ethanenitrile
• 英文别名: N-(cyanomethyl)benzamide；Benzamidoacetonitrile
• CAS: 5692-27-3
• 化学式: C₉H₈N₂O
• mdl: MFCD01212017
• 分子量: 160.175
• InChiKey: LPKZSPQPPSEVSX-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C(Solv: ethanol (64-17-5))
• 沸点：
  409.1±28.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 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：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  N-(氰基甲基)-苯甲酰胺 在 manganese(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 methyl 2-(benzamidomethyl)thiazole-4-carboxylate
  参考文献：
  名称：

  肽。第二十一部分。半胱氨酸衍生的某些噻唑啉的脱氢

  摘要：

  的酯2-烷基Δ 2噻唑啉-4-羧酸顺利通过菲醌脱氢成相应的噻唑衍生物。甲基2-苯甲酰氨基Δ 2噻唑啉-4-羧酸叔丁酯通过phenenthraquinone但迅速由二氧化锰仅缓慢地脱氢。讨论了这些反应在肽中噻唑啉环检测中的可能应用。

  DOI：

  10.1039/j39660001061
• 作为产物：
  描述：

  benzylidene-(4-methylsulfanyl-2-phenyl-oxazol-5-yl)-amine 在 盐酸 、 镍 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 N-(氰基甲基)-苯甲酰胺
  参考文献：
  名称：

  Heterocyclic Ring-Closure Reactions. I. A Novel Oxazole Synthesis from S,S'-Dialkyl or -Diaryl Dithiooxaldiimidates and Aromatic Aldehydes^1a

  摘要：

  DOI：

  10.1021/jo01349a033

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。
• 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。
• -Acylated α-aminonitriles and their conversion into 5-aminooxazole, 5(4)-oxazolone and 4(5)-imidazolone derivatives
  作者：P. Verschave、J. Vekemans、G. Hoornaert

  DOI：10.1016/0040-4020(84)80023-x

  日期：1984.1

  In contrast with the reaction of α-aminonitriles a, the corresponding -acylated α-aminonitriles b-f and oxalyl chloride do not yield pyrazinone derivatives, but 5-aminooxazoles - or 4(5)-imidazolones , the latter being converted in some cases into imidazo [2,1-]isoquinoline-2,5,6(3)-triones. Reactions of compounds b-f and ethyl chlorooxoacetate provide evidence for a 5(4)-iminooxazole intermediate

  与α-氨基腈a的反应相反，相应的酰化α-氨基腈bf和草酰氯不会生成吡嗪酮衍生物，但会生成5-氨基恶唑-或4（5 ）-咪唑啉酮，后者在某些情况下会转化为咪唑并[2,1- ]异喹啉-2,5,6 （3 ）-三酮。化合物bf与氯氧乙酸乙酯的反应提供了5（4 ）-亚氨基恶唑中间体的证据，该中间体芳香化生成5-氨基恶唑- 。但是，不可芳香化的中间体类型-水解后可分离为5（4 ）y-恶唑酮-经过催化的Dimroth型重排生成咪唑酮衍生物。
• 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。