E-ethyl cyano(phenylhydrazono)acetate | 27097-85-4

• 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: E-ethyl cyano(phenylhydrazono)acetate
• 英文别名: phenylhydrazono ethyl cyanoacetate；E-2-Cyano-2-phenylhydrazonoessigsaeureethylester；Ethyl (2E)-cyano(phenylhydrazono)ethanoate；ethyl (2E)-2-cyano-2-(phenylhydrazinylidene)acetate
• CAS: 27097-85-4
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: NVOMLTILICGMJT-GXDHUFHOSA-N

物化性质

• 熔点：
  124-125 °C(Solv: benzene (71-43-2))
• 沸点：
  322.4±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  E-ethyl cyano(phenylhydrazono)acetate 反应 0.5h， 生成 Z-ethyl cyano(phenylhydrazono)acetate
  参考文献：
  名称：

  Brecknell,D.J. et al., Australian Journal of Chemistry, 1969, vol. 22, p. 1915 - 1922

  摘要：

  DOI：
• 作为产物：
  描述：

  氯化重氮苯 、 氰乙酸甲酯 生成 E-ethyl cyano(phenylhydrazono)acetate
  参考文献：
  名称：

  BESTMANN H. J.; SCHMID G.; SANDMEIER D., TETRAHEDRON LETT., 1980, 21, NO 31, 2939-2942

  摘要：

  DOI：

文献信息

• Studies with 3-functionally substituted 2-arylhydrazononitriles: A new route to 3-substituted-2-arylhydrazononitriles, 4-amino-pyrazole-5-carbonitriles, azadienes and cinnolines
  作者：Ramadan M. Abdel-Motaleb、Abdel-Moneim A. Makhloof、Hamada M. Ibrahim、Mohamed H. Elnagdi

  DOI：10.1002/jhet.5570430418

  日期：2006.7

  3-Amino-3-phenyl-2-phenylazoacrylonitrile 6 is obtained in good yield via reaction of 5 with phenyl magnesium bromide. The compound 6 is readily converted into 4a. The so formed alkanenitrile reacted with phenylmagnesium bromide to yield 8. Compound 8 could be also obtained from reaction of 9 with phenylmagnesium bromide. The arylhydrazononitriles 8 and 4a reacted with chloroacetonitrile to yield the 4-aminopyrazoles

  通过使5与苯基溴化镁反应，可以高收率获得3-氨基-3-苯基-2-苯基偶氮丙烯腈6。化合物6易于转化为4a。如此形成的链烷腈与苯基溴化镁反应生成8。化合物8也可以由9与苯基溴化镁反应获得。芳基肼腈8和4a与氯乙腈反应，得到4-氨基吡唑12a，b。化合物12a与乙酸酐反应生成15a并与苯甲酰氯一起生成吡唑16，将其转化为15b。将10回流在乙酸中，得到氮杂二烯21和辛啉22的混合物。氮杂二烯21通过热或光化学方式转化为22。
• Improved Protocol for Thorpe Reaction: Synthesis of 4‐Amino‐1‐arylpyrazole using Solid–Liquid Phase‐Transfer Conditions
  作者：Nirmal D. Desai、Rina D. Shah

  DOI：10.1080/00397910701767023

  日期：2008.1.1

  Solid - liquid phase-transfer conditions were employed for the first time in the Thorpe reaction to synthesize 4-amino-1-aryl-3,5-substituted-1H-pyrazoles 3. Aryl amines were diazotized and coupled with various active methylene compounds such as cyano acetamide, cyanoacetophenone, malononitrile, and ethyl cyanoacetate, resulting into alpha-arylhydrazononitriles 1. Cyclization of 1 using alpha-bromo ketones or esters resulted in compounds 3.
• Flash vacuum pyrolysis of 3-oxo-2-arylhydrazonopropanals and related derivatives
  作者：Yehia A Ibrahim、Kamini Kaul、Nouria A Al-Awadi

  DOI：10.1016/s0040-4020(01)01040-7

  日期：2001.12
• Prasad, Durgeshwari; Prasad, Nagendra; Prasad, Radha M., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1397 - 1399
  作者：Prasad, Durgeshwari、Prasad, Nagendra、Prasad, Radha M.、Ferrier, Robert J.、Milgate, Stephen M.

  DOI：——

  日期：——
• Patel, Himatkumar V.; Vyas, Kavita A.; Pandey, Sudhanshu P., Organic Preparations and Procedures International, 1994, vol. 26, # 1, p. 118 - 120
  作者：Patel, Himatkumar V.、Vyas, Kavita A.、Pandey, Sudhanshu P.、Fernandes, Peter S.

  DOI：——

  日期：——