2,5-dimethyl-3-(2-methylpropyl)pyrazine | 32736-94-0

• 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: 2,5-dimethyl-3-(2-methylpropyl)pyrazine
• 英文别名: 2,5-dimethyl-3-isobutylpyrazine；3-isobutyl-2,5-dimethyl-pyrazine；2,5-dimethyl-3-(2-methylpropyl)-pyrazine；2,5-Dimethyl-3-isobutylpyrazin；2-Isobutyl-3,6-dimethylpyrazin
• CAS: 32736-94-0
• 化学式: C₁₀H₁₆N₂
• 分子量: 164.25
• InChiKey: KEJOEQXAEQCAKT-UHFFFAOYSA-N

物化性质

• 沸点：
  222.4±35.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)
• LogP：
  2.511 (est)
• 保留指数：
  1184;1221.3;1184;1188.3;1194.4

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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 magnesium 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 2,5-dimethyl-3-(2-methylpropyl)pyrazine
  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

• Novel Pyrazines from the Myxobacterium<i>Chondromyces crocatus</i>and Marine Bacteria
  作者：Jeroen S. Dickschat、Hans Reichenbach、Irene Wagner-Döbler、Stefan Schulz

  DOI：10.1002/ejoc.200500280

  日期：2005.10

  iron-catalysed coupling of chloropyrazines with Grignard reagents or condensation of azido ketones as key steps. The synthetic material allowed the identification of two previously unknown attractants of bacterial origin for the pineapple beetle Carpophilus humeralis, namely 3-methoxy-2-(1-methylpropyl)-5-(2-methylpropyl)pyrazine (17) and 3-methoxy-2,5-bis(1-methylpropyl)pyrazine (52). Several 2,5-dialkylpyrazines

  使用 CLSA 或 SPME 顶空方法收集了来自北海的 2 株粘杆菌 Chondromyces crocatus 和 7 株海洋 Alphaproteobacteria 释放的挥发物，并通过 GC-MS 进行分析。在 C. crocatus 的提取物中鉴定出属于不同类别的 27 种吡嗪。2,5-二烷基吡嗪和相关的3-甲氧基-2,5-二烷基吡嗪占主导地位。从天然来源获得了几种吡嗪，如 2-(1-甲基乙烯基)-5-(1-甲基乙基)吡嗪 (7) 和具有甲基、异丙基、异丁基或仲丁基侧链的 3-甲氧基-2,5-二烷基吡嗪首次。鉴定必须依赖合成参考材料，这些参考材料是使用 Furstner 铁催化的氯吡嗪与格氏试剂偶联或叠氮酮缩合获得的关键步骤。合成材料允许鉴定两种以前未知的细菌来源的菠萝甲虫 Carpophilus humeralis 引诱剂，即 3-甲氧基-2-(1-甲基丙基)-5-(2-甲基丙基)吡嗪
• 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。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• IMAGING CONTRAST AGENTS AND USES THEREOF
  申请人：Morrow Janet R.

  公开号：US20140193344A1

  公开（公告）日：2014-07-10

  Provided are macrocyclic compounds having a macrocyclic core which has at least one macrocyclic donor and at least one pendant group which has at least one donor group. The macrocyclic compounds can be complexed to Fe(II) and Ni(II). The macrocyclic compounds can be used in imaging methods. For example, the compounds can be used MRI paraCEST contrast agents.

  提供的是具有至少一个大环供体和至少一个带有至少一个供体基团的挂基团的大环化合物的大环核。这些大环化合物可以与Fe（II）和Ni（II）形成络合物。这些大环化合物可以用于成像方法。例如，这些化合物可以用于MRI paraCEST对比剂。

表征谱图