3-ethenyl-2,5-dimethylpyrazine | 80935-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-ethenyl-2,5-dimethylpyrazine
• 英文别名: 2,5-dimethyl-3-vinylpyrazine；2,5-dimethyl-3-vinyl-pyrazine；2,5-Dimethyl-3-vinylpyrazin
• CAS: 80935-98-4
• 化学式: C₈H₁₀N₂
• 分子量: 134.181
• InChiKey: JLPZQZIYSREPPU-UHFFFAOYSA-N

物化性质

• 保留指数：
  1078

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二甲基吡嗪 1-氧化物 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 3-ethenyl-2,5-dimethylpyrazine
  参考文献：
  名称：

  Pheromone synthesis. Part 261: Synthesis of four pyrazines produced by females of the Korean apricot wasp, Eurytoma maslovskii

  摘要：

  Four pyrazines were synthesized as sex specific volatiles of female Korean apricot wasp, Eurytoma maslovskii. They are 2,5-dimethy1-3-vinylpyrazine (1), 2,5-dimethy1-3-(2-methylpropyl)pyrazine (2), 2,5-dimethyl-3-(2-methylbutyl)pyrazine (3), and 2,5-dimethyl-3-(3-methylbutylpyrazine (4). They were synthesized in 74-85% yields by Pd- or Fe-catalyzed cross-coupling reactions between 3-chloro-2,5-dimethylpyrazine and CH2=CHBF3K or RMgBr. The present synthesis of 1 is the most reliable and scalable one to date. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.06.055

文献信息

• Impact of the N-Terminal Amino Acid on the Formation of Pyrazines from Peptides in Maillard Model Systems
  作者：Fien Van Lancker、An Adams、Norbert De Kimpe

  DOI：10.1021/jf301315b

  日期：2012.5.9

  peptide C-terminal amino acid was investigated, this study focused on the influence of the peptide N-terminal amino acid on the production of pyrazines in model reactions of glucose, methylglyoxal, or glyoxal. Nine different dipeptides and three tripeptides were selected. It was shown that the structure of the N-terminal amino acid is determinative for the overall pyrazine production. Especially, the production

  文献中美拉德反应研究的一小部分集中在碳水化合物和肽之间的反应上。因此，在先前的研究中，其中该肽的影响的延续Ç端氨基酸进行了研究，该研究集中在肽的影响Ñ端氨基酸上生产的葡萄糖，甲基乙二醛的模型反应吡嗪类，或乙二醛。选择了九个不同的二肽和三个三肽。结果表明，N-末端氨基酸的结构决定了吡嗪的总产量。特别是在N上脯氨酸，缬氨酸或亮氨酸的情况下，2,5（6）-二甲基吡嗪和三甲基吡嗪的产量较低-末端，而对于甘氨酸，丙氨酸或丝氨酸则很高。与烷基取代的吡嗪相反，在用游离氨基酸进行实验的情况下，未取代的吡嗪总是产生更多。显然，对此观察结果必须负责不同的机制。这项研究清楚地说明了肽产生风味化合物（例如吡嗪）的能力。
• Formation of Pyrazines in Maillard Model Systems of Lysine-Containing Dipeptides
  作者：Fien Van Lancker、An Adams、Norbert De Kimpe

  DOI：10.1021/jf903898t

  日期：2010.2.24

  respectively. Generally, the pyrazines were produced more in the case of dipeptides as compared to free amino acids. For reactions with glucose and methylglyoxal, this difference was mainly caused by the large amounts of 2,5(6)-dimethylpyrazine and trimethylpyrazine produced from the reactions with dipeptides. For reactions with glyoxal, the difference in pyrazine production was rather small and mostly unsubstituted

  尽管有关美拉德反应的大多数研究都集中在游离氨基酸上，但是关于肽和蛋白质对食品化学中这一重要反应的影响的信息很少。因此，研究了葡萄糖，甲基乙二醛或乙二醛与八种二肽与赖氨酸在N端的模型反应的形成，并与相应的游离氨基酸进行了对比，方法是通过搅拌棒吸附萃取（SBSE），然后是GC-MS分析。包含葡萄糖，甲基乙二醛和乙二醛的二肽的反应混合物分别产生27种，18种和2种不同的吡嗪。通常，与二肽相比，与游离氨基酸相比，吡嗪的产生更多。对于与葡萄糖和甲基乙二醛的反应，这种差异主要是由于与二肽反应产生的大量2,5（6）-二甲基吡嗪和三甲基吡嗪引起的。对于与乙二醛的反应，吡嗪生产的差异很小，并且形成了大部分未取代的吡嗪。提出并评价了由二肽形成吡嗪的反应机理。这项研究清楚地说明了肽产生风味化合物的能力，这种风味化合物可能不同于通过与游离氨基酸进行相应反应而获得的风味化合物。
• Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine
  作者：Toshinari H Kurniadi、Rachid Bel Rhlid、Marcel-A Juillerat、Thierry Gefflaut、Jean Bolte、Ralf G Berger

  DOI：10.1016/s0040-4020(03)00948-7

  日期：2003.8

  2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels–Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was

  通过新的化学路线合成了香气化合物2-乙烯基-3,5-二甲基吡嗪1和3-乙烯基-2,5-二甲基吡嗪2。合成的关键步骤包括1- [双环[2.2.1] 5-庚-2-基] -1,2-丙二酮和1,2-丙二胺的环缩合，所得5,6-二氢吡嗪的芳构化，以及随后发生Retro-Diels-Alder反应，生成吡嗪1和2。当将内基-1- [双环[2.2.1] 5-庚-2-基] -1，1,2-丙二酮用作内衬时，可获得过量（8：2）的强效吡嗪1。
• Glucose-Histidine Heyns compound: Preparation, characterization and fragrance enhancement
  作者：Kuan Li、Jinling Wang、Yadong Zhuang、Guangxiang Yuan、Yuxiu Li、Xiaolan Zhu

  DOI：10.1016/j.carres.2023.108922

  日期：2023.10

  (Glu-His), one of Heyns rearrangement products (HRPs), was prepared by condensation, dehydration and rearrangement using l-Histidine and d-Fructose as raw materials with methanol as solvent. The response surface method (RSM) was used to improve yield of product and the optimal reaction condition was as following: the original ratio of Fru:His was 1.2:1 and the temperature and time of reaction was

  N-(2-脱氧-D-葡萄糖-2-基)-L-组氨酸(Glu-His)是Heyns重排产物(HRP)之一，由l-组氨酸和d-果糖通过缩合、脱水和重排制备而成以甲醇为溶剂，以甲醇为原料。采用响应面法（RSM）提高产物收率，最佳反应条件为：原Fru:His比例为1.2:1，反应温度73.2℃，反应时间4.7h，最终产品收率74.10%，纯度99.7%。产物结构经IR、NMR鉴定，经高分辨质谱(HRMS)和UPLC-MS/MS鉴定为C 12 H 19 N 3 O 7 (317.1 Da)。Glu-His的热解行为表明，其初始热解温度为145.2℃，在800℃时总失重达到70.61%。热解产物数量随着温度的升高而增加，主要热解产物为吡喃、呋喃、吡嗪、吡咯、吡啶、吲哚等，具有焦甜、烘烤、坚果、甜味和花香特征。最后考察了Glu-His在再造烟梗（RTS）制备中的增香效果，感官评价结果表明，RTS卷烟烟气更
• PROTON CONDUCTING FILM HAVING CROSSLINKED STRUCTURE AND FUEL CELL
  申请人：TOYOTA JIDOSHA KABUSHIKI KAISHA

  公开号：EP3644420A1

  公开（公告）日：2020-04-29

  A proton conducting film includes a polymer having a first part and a second part which are connected by a covalent bond and a plasticizer. The first parts aggregate with each other to form a domain at an operation temperature of the proton conducting film, and the second part crosslinks the domains. The second part has a proton accepting group, and the plasticizer contains a proton donating compound having a pKa of 2.5 or less, and thus the plasticizer penetrates into the second part, and a glass transition temperature of the polymer is lowered compared to when the plasticizer is not included.

  质子传导薄膜包括一种聚合物，它具有通过共价键和增塑剂连接的第一部分和第二部分。在质子传导薄膜的工作温度下，第一部分相互聚合形成畴，第二部分交联畴。第二部分具有质子接受基团，增塑剂含有 pKa 值为 2.5 或更小的质子捐赠化合物，因此增塑剂可渗透到第二部分，与不含增塑剂时相比，聚合物的玻璃化转变温度会降低。