5-(叔丁基)吡嗪-2,3-二甲腈 | 51440-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(叔丁基)吡嗪-2,3-二甲腈
• 英文名称: 5-(tert-butyl)pyrazine-2,3-dicarbonitrile
• 英文别名: 5-tert-butylpyrazine-2,3-dicarbonitrile；t-BuPyz(CN)₂；5-tert-butyl-pyrazine-2,3-dicarbonitrile；5-tert.Butyl-2,3-dicyanopyrazin
• CAS: 51440-69-8
• 化学式: C₁₀H₁₀N₄
• mdl: MFCD05863491
• 分子量: 186.216
• InChiKey: DMBXBPQXFZRCIT-UHFFFAOYSA-N

物化性质

• 沸点：
  344.2±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(叔丁基)吡嗪-2,3-二甲腈 在 copper diacetate 作用下， 生成
  参考文献：
  名称：

  Synthesis and Mesomorphic Properties of Substituted Pyrazinoporphyrazines

  摘要：

  DOI：

  10.1080/15421406.2011.609394
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 selenium(IV) oxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 5-(叔丁基)吡嗪-2,3-二甲腈
  参考文献：
  名称：

  Nakamura, Akira; Ataka, Toshiei; Segawa, Hirozo, Agricultural and Biological Chemistry, 1983, vol. 47, # 7, p. 1555 - 1560

  摘要：

  DOI：

文献信息

• Synthesis of a tetrapyrazinoporphyrazine-based fluorescent sensor for detection of Cu2+ ion
  作者：Chang Young Jung、Wang Yao、Jong Min Park、Joong Hyun Cho、Dae Hyun Kim、Jae Yun Jaung

  DOI：10.1007/s10847-017-0735-3

  日期：2017.10

  novel tetrapyrazinoporphyrazine-based fluorescent sensor for Cu2+ ion was synthesized and fully characterized by 1H NMR, MALDI-TOF MS, and elemental analysis. A tetrapyrazinoporphyrazine substituent was used as the reporting group and a 2,2′-dipyridylamine moiety was employed as the recognition group. The effects of various metal ions on the absorption and emission spectra of the designed molecule were

  在这项研究中，合成了一种新型的基于四吡嗪并四氮杂卟啉的 Cu2+ 离子荧光传感器，并通过 1H NMR、MALDI-TOF MS 和元素分析对其进行了充分表征。四吡嗪并四氮杂卟啉取代基用作报告基团，2,2'-二吡啶胺部分用作识别基团。研究了各种金属离子对设计分子的吸收和发射光谱的影响，证明该化合物对 Cu2+ 离子显示出选择性和敏感性。添加Cu2+离子后，基于四吡嗪并四氮杂卟啉的传感器的荧光强度在655nm处逐渐降低。为了确认 2,2'-二吡啶基胺部分对 Cu2+ 离子的选择性结合能力，使用四吡嗪并四氮杂卟啉衍生物与溴代替 2 进行了比较研究，2'-二吡啶胺部分。此外，合成化合物对Cu2+离子的缔合常数和检测限值来自重复滴定实验。此外，通过使用化合物和乙二胺四乙酸的额外测试证实了制备的传感器的可逆性。
• <i>tert</i>-Butyl substituted hexaazasubphthalocyanine: Synthesis, isolation of <i>C</i>₁ and <i>C</i>₃ regioisomers and their spectral-luminescence study
  作者：Alexey S. Panteleev、Ivan A. Skvortsov、Oskar I. Koifman、Pavel A. Stuzhin

  DOI：10.1142/s108842462150022x

  日期：2021.4

  By cyclotrimerization of tert-butyl substituted pyrazine-2,3-dicarbonitrile in the presence of boron trichloride, two positional isomers ([Formula: see text] and [Formula: see text] symmetry) of the corresponding boron(III) tripyrazinosubporphyrazines were first obtained and efficiently separated by column chromatography. The new compounds were characterized by MALDI mass-spectrometry, UV-visible and ¹H NMR spectroscopy. A Q-band in the electronic absorption spectra for both fractions was observed at [Formula: see text]530 nm, which is typical for tripyrazinosubporphyrazines. The fluorescence quantum yield for the regioisomer with lower symmetry ([Formula: see text] is 1.5 times higher than for the more symmerical [Formula: see text] species ([Formula: see text] = 0.37 and 0.28, respectively). Comparative spectrophotometric study of the basic properies reveals that hexaaza substitution in benzene rings of tert-butyl substituted subphthalocyanine decreases the basic properties of meso-nitrogen atoms.

  在三氯化硼存在下，通过叔丁基取代的吡嗪-2,3-二甲腈的环三聚反应，首次获得了相应的硼（III）三吡嗪次卟啉的两种位置异构体（[式：见正文]和[式：见正文]对称），并通过柱层析进行了有效分离。新化合物通过 MALDI 质谱、紫外-可见光和 1H NMR 光谱进行了表征。两种馏分的电子吸收光谱在 [式中：见正文] 530 nm 处都出现了 Q 波段，这是三嗪亚卟吩的典型特征。对称性较低的区域异构体（[式：见正文]）的荧光量子产率是对称性较高的[式：见正文]物种（[式：见正文]分别为 0.37 和 0.28）的 1.5 倍。对基本性质进行的分光光度比较研究表明，叔丁基取代亚酞菁苯环中的六氮取代会降低中氮原子的基本性质。
• Synthesis of isoindole-diimine and its derivatives without ammonia gas bubbling
  作者：Yumiko Igarashi、Yusuke Okada、Atsuya Muranaka、Masahiro Suzuki、Nagao Kobayashi

  DOI：10.1142/s1088424623500116

  日期：2023.1

  Isoindole-diimine, which can be obtained by bubbling ammonia gas into a solution of phthalonitrile derivatives in the presence of Na[Formula: see text] ion, is a final and best precursor for phthalocyanine synthesis. In this study, isoindole-diimine and various derivatives have been prepared without bubbling ammonia gas using in situ generated ammonia that was produced from formamide and a strong alkali such as NaOH and NaNH₂. A longer reaction time, higher temperature, and larger amount of formamide were required for phthalonitrile derivatives with electron-donating groups, but this method is recommendable in that an NH₃ gas cylinder and concomitant gas regulator, which are not inexpensive, are not required. Attempts were made to interpret the IR and absorption spectra of the resultant diimines. The signals due to imino proton or N-H of diimino compounds were experimentally found to appear at around 8.2[Formula: see text]9.5 ppm in ¹H-NMR and ca. 3500–3000 cm[Formula: see text] in IR spectra.

  在 Na[式：见正文]离子存在下，向邻苯二腈衍生物溶液中通入氨气可得到异吲哚二胺，它是合成酞菁的最终和最佳前体。本研究利用甲酰胺和 NaOH、NaNH2 等强碱原位生成的氨气，在不鼓泡氨气的情况下制备了异吲哚二胺和各种衍生物。对于带有电子捐赠基团的邻苯二腈衍生物来说，需要更长的反应时间、更高的温度和更多的甲酰胺，但这种方法是值得推荐的，因为它不需要 NH3 气瓶和相应的气体调节器（价格并不便宜）。我们尝试解释生成的二亚胺的红外光谱和吸收光谱。实验发现，二亚胺化合物的亚氨基质子或 N-H 信号在 1H-NMR 中约为 8.2[式：见正文]9.5ppm，在红外光谱中约为 3500-3000 cm[式：见正文]。
• Elemental Sulfur-Mediated Synthesis of Quinoxalines from Sulfoxonium Ylides
  作者：Trayambek Nath Chaubey、Paran J. Borpatra、Satyendra Kumar Pandey

  DOI：10.1021/acs.orglett.3c01907

  日期：2023.7.21

  A novel straightforward and catalyst-free approach for synthesizing quinoxaline derivatives from sulfoxonium ylides and o-phenylenediamines mediated by elemental sulfur has been described. Due to the simple and mild reaction conditions, the sulfoxonium ylides and o-phenylenediamines decorated with different functional groups furnished moderate to high yields of quinoxaline derivatives and were well

  描述了一种由硫叶立德和邻苯二胺以元素硫介导合成喹喔啉衍生物的简单且无催化剂的新方法。由于反应条件简单温和，不同官能团修饰的亚砜叶立德和邻苯二胺提供了中等到高产率的喹喔啉衍生物，并且具有良好的耐受性。最后，使用大规模反应、吡嗪的合成和一些生物活性化合物来说明所开发方法的潜在效用。
• Synthesis and properties of lanthanide complexes with tetrapyrazinoporphyrazine and its substituted derivatives
  作者：T. A. Lebedeva、V. P. Kulinich、G. P. Shaposhnikov、S. V. Efimova、A. B. Korzhenevskii、O. I. Koifman

  DOI：10.1134/s1070363207110175

  日期：2007.11

  Reactions of dicyanopyrazine and its tert-butyl-, diphenyl-, and dipyridyl-substituted derivatives with erbium, thulium, ytterbium, and lutetium chlorides, acetates, and acetylacetonates gave the corresponding tetrapyrazinoporphyrazine metal complexes which were characterized by elemental analyses, and IR, H-1 NMR, and electronic absorption spectra. The stability of the complexes to thermooxidative decomposition in air was also studied.