3-CL-C6H4Nhn=C(CN)cooet | 1321690-51-0

• 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: 3-CL-C6H4Nhn=C(CN)cooet
• 英文别名: ethyl (2E)-2-[(3-chlorophenyl)hydrazinylidene]-2-cyanoacetate
• CAS: 1321690-51-0
• 化学式: C₁₁H₁₀ClN₃O₂
• 分子量: 251.672
• InChiKey: FSIFRTHCIGOKNH-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 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：

  3-CL-C6H4Nhn=C(CN)cooet 、 溴乙酸乙酯 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以78%的产率得到diethyl 4-amino-1-(3-chlorophenyl)-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：

  氰乙酸乙酯 、 3-氯苯胺 生成 3-CL-C6H4Nhn=C(CN)cooet
  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

• 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.