2-amino-3-(2,5-dimethyl-1H-pyrrol-1-yl)-(2Z)-butene-1,4-dinitrile | 51802-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-3-(2,5-dimethyl-1H-pyrrol-1-yl)-(2Z)-butene-1,4-dinitrile
• 英文别名: N-(2-amino-1,2-dicyanoethenyl)-2,5-dimethylpyrrole；(2Z)-2-Amino-3-(2,5-dimethyl-1H-pyrrol-1-yl)-2-butenedinitrile；(Z)-2-amino-3-(2,5-dimethylpyrrol-1-yl)but-2-enedinitrile
• CAS: 51802-32-5
• 化学式: C₁₀H₁₀N₄
• 分子量: 186.216
• InChiKey: XRRBBXCHJLFCNY-KTKRTIGZSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  264.0±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-(2,5-dimethyl-1H-pyrrol-1-yl)-(2Z)-butene-1,4-dinitrile 在 碘 、 sodium hydride 、 magnesium 、 正丁醇 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 23.0h， 生成 [2,7,12,17-tetrakis(dimethylamino)-3,8,13,18-tetrakis(2,5-dimethyl-1H-pyrrol-1-yl)porphyrazinato]magnesium(II)
  参考文献：
  名称：

  Synthesis, characteristics and photochemical studies of novel porphyrazines possessing peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino groups

  摘要：

  The synthesis and physicochemical properties of novel porphyrazines possessing an alternate system of two peripheral substituents, 2,5-dimethylpyrrol-1-yl and dimethylamino, are presented. All the macrocycles were subjected to HPLC purity studies. Spectroscopic studies of magnesium(II) porphyrazine encompassed steady state absorption, emission measurements, including fluorescence decays, transient absorption spectra, and thermoluminescence. Additionally, magnesium(II) porphyrazine was found to be a moderate photosensitizer with singlet oxygen generation values of 0.12 and 0.14 in DMF and DMSO, respectively. Comparison of the quantum yields of singlet oxygen generation before and after deoxygenation showed that the photodynamic effect of magnesium(II) porphyrazine is governed by the photosensitization mechanism II. Magnesium(II) and manganese(III) porphyrazines were characterized using X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.010
• 作为产物：
  描述：

  2,5-己二酮 、 二氨基马来腈 在 草酸 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 2-amino-3-(2,5-dimethyl-1H-pyrrol-1-yl)-(2Z)-butene-1,4-dinitrile
  参考文献：
  名称：

  Synthesis, characteristics and photochemical studies of novel porphyrazines possessing peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino groups

  摘要：

  The synthesis and physicochemical properties of novel porphyrazines possessing an alternate system of two peripheral substituents, 2,5-dimethylpyrrol-1-yl and dimethylamino, are presented. All the macrocycles were subjected to HPLC purity studies. Spectroscopic studies of magnesium(II) porphyrazine encompassed steady state absorption, emission measurements, including fluorescence decays, transient absorption spectra, and thermoluminescence. Additionally, magnesium(II) porphyrazine was found to be a moderate photosensitizer with singlet oxygen generation values of 0.12 and 0.14 in DMF and DMSO, respectively. Comparison of the quantum yields of singlet oxygen generation before and after deoxygenation showed that the photodynamic effect of magnesium(II) porphyrazine is governed by the photosensitization mechanism II. Magnesium(II) and manganese(III) porphyrazines were characterized using X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.010

文献信息

• Porphyrazines with bulky peripheral pyrrolyl substituents – Synthesis via microwave-assisted Suzuki-Miyaura cross-coupling reaction, optical and electrochemical properties
  作者：Wojciech Szczolko、Tomasz Koczorowski、Barbara Wicher、Michal Kryjewski、Zuzanna Krakowska、Ewa Tykarska、Tomasz Goslinski

  DOI：10.1016/j.dyepig.2022.110607

  日期：2022.10

  Microwave-assisted organic synthesis approaches were used in the Paal-Knorr reaction leading to the modified diaminomaleonitrile intermediates and the Suzuki-Miyaura reaction, which allowed the obtaining of porphyrazine derivative. All compounds were characterized using UV–Vis, 1H and 13C NMR, including 2D techniques, as well as MS (ES or MALDI). An X-ray analysis of magnesium(II) porphyrazine with peripheral

  报道了具有外围 3,4-二卤化物-2,5-二甲基吡咯-1-基和二甲氨基外围基团的新型氨基卟啉的合成。Suzuki-Miyaura 与苯基硼酸的交叉偶联反应用于将镁 (II) 卟啉与二甲氨基和 3,4-二溴-2,5-二甲基吡咯-1-基基团转化为具有庞大 2,5-二甲基-3 的类似物,4-二苯基吡咯-1-基部分。微波辅助有机合成方法用于 Paal-Knorr 反应，得到改性二氨基马来腈中间体和 Suzuki-Miyaura 反应，从而获得四氮杂卟啉衍生物。使用 UV-Vis、1 H 和13对所有化合物进行了表征C NMR，包括 2D 技术，以及 MS（ES 或 MALDI）。还对具有外围 3,4-二溴-2,5-二甲基吡咯-1-基和二甲氨基取代基的镁 (II) 卟啉进行了 X 射线分析。使用循环和差分脉冲伏安法评估了所有获得的四氮杂卟啉大环化合物的电化学性质。新大环对氧化/还原过程的敏感性取决于其大环外围是否存在卤化物取代基。
• ——
  作者：Joel T. Mague、Etim E. Eduok

  DOI：10.1023/a:1009557123632

  日期：——

  For the synthesis of precursors to cellulose-based ion exchange materials, the condensation of diaminomaleonitrile with 2,4-pentanedione and 2,5-hexanedione was explored. Whilst the former diketone yielded the expected l,4-diazepine (2), the latter gave either a pyrrole derivative (3) or an unusual triazabicyclononene (4), depending on the conditions lsed. Compound 4 crystallizes in the monoclinic space group P2(1)/c with a = 8.9313(10) Angstrom, b = 9.0370(7) Angstrom, c = 11.4448(9)Angstrom. beta = 102.48(8)degrees, V = 901.89(14) Angstrom (3), and Z = 4. Compound 3 crystallizes in the orthorhombic space group Pna2(1) with a = 12.0342(8) Angstrom, b = 8.3760(8) Angstrom, c = 10.7026(11) Angstrom, V = 1078.81(17) Angstrom (3), and Z = 4. Compound 4 crystallizes in the monoclinic space group P2(1)/c with a = 9.0157(5) Angstrom, b = 13.5374(9) Angstrom, c = 12.8751(16) Angstrom, beta = 99.506(5)degrees, V = 1549.82(15) Angstrom (3), and Z = 4. In both 3 and 4 the aminovinyl substituent shows evidence for involvement of the lone pair on nitrogen with the carbon pi -system. Also, 3 and 4 are highly associated in the solid state via hydrogen bonding.
• Synthesis, characteristics and photochemical studies of novel porphyrazines possessing peripheral 2,5-dimethylpyrrol-1-yl and dimethylamino groups
  作者：Wojciech Szczolko、Lukasz Sobotta、Piotr Fita、Tomasz Koczorowski、Michal Mikus、Maria Gdaniec、Aleksandra Orzechowska、Kvetoslava Burda、Stanislaw Sobiak、Marcin Wierzchowski、Jadwiga Mielcarek、Ewa Tykarska、Tomasz Goslinski

  DOI：10.1016/j.tetlet.2012.02.010

  日期：2012.4

  The synthesis and physicochemical properties of novel porphyrazines possessing an alternate system of two peripheral substituents, 2,5-dimethylpyrrol-1-yl and dimethylamino, are presented. All the macrocycles were subjected to HPLC purity studies. Spectroscopic studies of magnesium(II) porphyrazine encompassed steady state absorption, emission measurements, including fluorescence decays, transient absorption spectra, and thermoluminescence. Additionally, magnesium(II) porphyrazine was found to be a moderate photosensitizer with singlet oxygen generation values of 0.12 and 0.14 in DMF and DMSO, respectively. Comparison of the quantum yields of singlet oxygen generation before and after deoxygenation showed that the photodynamic effect of magnesium(II) porphyrazine is governed by the photosensitization mechanism II. Magnesium(II) and manganese(III) porphyrazines were characterized using X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.