Cyano-[(4-methoxy-phenyl)-hydrazono]-acetic acid ethyl ester | 93845-48-8

• 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: Cyano-[(4-methoxy-phenyl)-hydrazono]-acetic acid ethyl ester
• 英文别名: ethyl (2E)-cyano[2-(4-methoxyphenyl)hydrazinylidene]ethanoate；ethyl (2E)-2-cyano-2-[(4-methoxyphenyl)hydrazinylidene]acetate
• CAS: 93845-48-8
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: TWYQKCVYLPBHNO-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 Cyano-[(4-methoxy-phenyl)-hydrazono]-acetic acid ethyl ester 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到diethyl 4-amino-1-(4-methoxyphenyl)-1H-pyrazole-3,5-dicarboxylate
  参考文献：
  名称：

  Improved Protocol for Thorpe Reaction: Synthesis of 4‐Amino‐1‐arylpyrazole using Solid–Liquid Phase‐Transfer Conditions

  摘要：

  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.

  DOI：

  10.1080/00397910701767023
• 作为产物：
  描述：

  甲氧苯胺 、 氰乙酸乙酯 生成 Cyano-[(4-methoxy-phenyl)-hydrazono]-acetic acid ethyl ester
  参考文献：
  名称：

  Improved Protocol for Thorpe Reaction: Synthesis of 4‐Amino‐1‐arylpyrazole using Solid–Liquid Phase‐Transfer Conditions

  摘要：

  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.

  DOI：

  10.1080/00397910701767023

文献信息

• 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：——
• Electrical conductivity, electronic absorption, IR and NMR studies on some ethyl cyanoacetate phenylhydrazones and their lanthanide complexes
  作者：A. A. Salem、Y. M. Issa、E. E. El-Shreafy

  DOI：10.1007/bf01997190

  日期：1997.4

  The electrical conductivities and the electronic, IR and NMR spectra were measured for some ethyl cyanoacetate phenylhydrazone derivatives and their lanthanide complexes in the temperature range 20-200 degrees C. Semiconducting behaviour was detected for these systems (positive d sigma/dT). A correlation was established between the electrical properties and the structures of the free ligand molecules and their complexes. The mechanism of the conduction process was evaluated. The electronic absorption spectra in ethanol were measured and are discussed. Elemental analyses were performed and the IR and NMR spectra (of the diamagnetic complexes) were measured to throw more light on the structures of these complexes.
• 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.