cyanoacetic acid cyclopentylidene hydrazide | 4980-23-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyanoacetic acid cyclopentylidene hydrazide
• 英文别名: 1-Cyclopentylidene-2-cyanoacetylhydrazine；2-cyano-N-(cyclopentylideneamino)acetamide
• CAS: 4980-23-8
• 化学式: C₈H₁₁N₃O
• 分子量: 165.195
• InChiKey: UOIPMXIPIXLWFF-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyanoacetic acid cyclopentylidene hydrazide 在 哌啶 、 聚合甲醛 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 6-Amino-5-oxospiro[1,3-dihydro-[1,2,4]triazolo[1,5-b]isoquinoline-2,1'-cyclopentane]-7,10-dicarbonitrile
  参考文献：
  名称：

  A new synthesis for 1,2,4-triazolo[1,5-a]-pyridines and 1,2,4-triazolo[1,5-a]isoquinolines

  摘要：

  Condensation of cyano acid hydrazide 1 with cyclopentanone in refluxing ethanolic piperidine yields hydrazone 2. With mixtures of aliphatic aldehydes and different active methylene reagents, 2 reacts to 1,2,4-triazolo[1,5-a]pyridines (8a-f). Compound 2 also reacts with arylidenes 9a-g to give triazolopyridines 10a-g. Reaction of 2 with aromatic aldehydes affords compounds 13a-c. Diazotation of 2 with aryldiazonium chloride in ethanol at 0 degrees C leads to the azo adducts 15a-d. The thieno-1,2,4-triazolopyridine 16 is obtained by reaction of 8a with elementary sulfur. 16 undergoes cycloaddition with omega-nitrostyrene, maleic anhydride, N-arylmalemide, and acrylonitrile yielding the isoquinolines 21-24. All new compounds have been characterized by their IR, H-1 NMR, and mass spectra.

  DOI：

  10.1007/bf00844690
• 作为产物：
  描述：

  氰乙酰肼 、 环戊酮 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以91%的产率得到cyanoacetic acid cyclopentylidene hydrazide
  参考文献：
  名称：

  Wardakhan, Wagnat W.; Youssef; Hamed, Faten I., Egyptian Journal of Chemistry, 2009, vol. 52, # 3, p. 349 - 360

  摘要：

  DOI：

文献信息

• The condensation of active methylene reagents with salicylaldehyde: Novel synthesis of chromene, azaanthracene, pyrano[3,4-c]chromene and chromeno[3,4-<i>c</i>]pyridine derivatives
  作者：Tarek M. Abu Elmaati、Fathi M. El-Taweel、Shymaa M. Elmougi、Abdelghani Elagamey

  DOI：10.1002/jhet.5570410502

  日期：2004.9

  On heating of the cyanoacetic acid cyclopentylidene hydrazide 1 with salicylaldehyde in the presence of bases the azaanthracene derivative 6 was formed. Also, reaction of 3 with malononitrile and ketones 10a,b afforded the pyrano[3,4-c]chromene 9 and chromeno[3,4-c]pyridine 11 respectively. A mechanism for these reactions is proposed.

  在碱的存在下，通过将氰基乙酸环戊叉酰肼1与水杨醛一起加热，形成了氮杂蒽衍生物6。同样，使3与丙二腈和酮10a，b反应，分别得到吡喃并[3,4- c ]亚甲基9和色诺[3,4- c ]吡啶11。提出了这些反应的机制。
• Synthesis of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetohydrazides via the Ritter reaction
  作者：Alexander G. Mikhailovskii、Evgeniya S. Pogorelova、Nataliya N. Pershina

  DOI：10.1007/s10593-020-02700-w

  日期：2020.5

  The Ritter cyclocondensation of 2-methyl-1-phenylpropan-2-ols with cyanoacetohydrazide hydrazones in PhMe–H2SO4 medium at 60–70°С for 20 min resulted in the formation of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)-acetohydrazides. The product of β-C-carbamoylation of the enamine moiety was also obtained.

  2-甲基-1-苯基丙-2-醇与氰基乙酰肼腙在 PhMe–H2SO4 介质中于 60–70°С 下进行 Ritter 环缩合反应 20 分钟，形成 N-亚苄基-和 N-亚烷基(3,3-)二烷基-3,4-二氢异喹啉-1(2H)-亚基)-乙酰肼。还获得了烯胺部分的β-C-氨基甲酰化产物。
• ——
  作者：K. N. Zelenin、S. V. Oleinik、V. V. Alekseev、A. A. Potekhin

  DOI：10.1023/a:1013126309514

  日期：——

  1D H-1 and C-13, and 2D H-1 NOESY NMR were used to establish that cyanoacetylhydrazones of aliphatic and aromatic aldehydes and ketones in CDCl3 and (CD3)(2)SO Solutions have a linear structure, exist as a mixture of geometric isomers by the C=N bond, and exhibit hindered amide rotation.
• Hussein; Sherif; Atalla, Polish Journal of Chemistry, 1996, vol. 70, # 7, p. 872 - 879
  作者：Hussein、Sherif、Atalla

  DOI：——

  日期：——
• A new synthesis for 1,2,4-triazolo[1,5-a]-pyridines and 1,2,4-triazolo[1,5-a]isoquinolines
  作者：A. M. Hussein、S. M. Sherif、A. A. Atalla

  DOI：10.1007/bf00844690

  日期：1996.11

  Condensation of cyano acid hydrazide 1 with cyclopentanone in refluxing ethanolic piperidine yields hydrazone 2. With mixtures of aliphatic aldehydes and different active methylene reagents, 2 reacts to 1,2,4-triazolo[1,5-a]pyridines (8a-f). Compound 2 also reacts with arylidenes 9a-g to give triazolopyridines 10a-g. Reaction of 2 with aromatic aldehydes affords compounds 13a-c. Diazotation of 2 with aryldiazonium chloride in ethanol at 0 degrees C leads to the azo adducts 15a-d. The thieno-1,2,4-triazolopyridine 16 is obtained by reaction of 8a with elementary sulfur. 16 undergoes cycloaddition with omega-nitrostyrene, maleic anhydride, N-arylmalemide, and acrylonitrile yielding the isoquinolines 21-24. All new compounds have been characterized by their IR, H-1 NMR, and mass spectra.