cyanoethylcyanoacrylate anthracene adduct | 1259537-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: cyanoethylcyanoacrylate anthracene adduct
• 英文别名: 2-Cyanoethyl 15-cyanotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate；2-cyanoethyl 15-cyanotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate
• CAS: 1259537-45-5
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: ASSZNVQMEAJRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 cyanoethylcyanoacrylate anthracene adduct 在 四磷十氧化物 、 对苯二酚 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 56.0h， 生成 2-cyanoethyl 2-cyanoacrylate 、 dibenzobarallene
  参考文献：
  名称：

  Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development

  摘要：

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.

  DOI：

  10.1021/ma400837h
• 作为产物：
  描述：

  乙基(15R)-15-氰基四环[6.6.2.02,7.09,14]十六-2,4,6,9,11,13-己烯-15-羧酸酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 cyanoethylcyanoacrylate anthracene adduct
  参考文献：
  名称：

  Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development

  摘要：

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.

  DOI：

  10.1021/ma400837h

文献信息

• Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development
  作者：Alfonso Bentolila、Jalindar Totre、Ilana Zozulia、Michal Levin-Elad、Abraham J. Domb

  DOI：10.1021/ma400837h

  日期：2013.6.25

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.