2,5-二甲基-3-(2-甲基丁基)吡嗪 | 72668-36-1

• 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: 2,5-二甲基-3-(2-甲基丁基)吡嗪
• 英文名称: 2,5-dimethyl-3-(2-methylbutyl)pyrazine
• CAS: 72668-36-1
• 化学式: C₁₁H₁₈N₂
• mdl: MFCD18449201
• 分子量: 178.277
• InChiKey: ARMKFUTVMIEDJN-UHFFFAOYSA-N

物化性质

• 保留指数：
  1308

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

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 2,5-二甲基-3-(2-甲基丁基)吡嗪
  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
• Pyrazine Alkylation with Aldehydes and Haloalkanes Using <i>N,N’</i> ‐Bis(trimethylsilyl)‐1,4‐dihydropyrazine Derivatives
  作者：Hayato Tsurugi、Minami Matsuno、Tomomi Kawakami、Kazushi Mashima

  DOI：10.1002/ejoc.202200862

  日期：2022.11.7

  N,N’-Bis(trimethylsilyl)-1,4-dihydropyrazines serves as starting materials for introducing alkyl groups into the parent pyrazine skeletons upon combined with aldehydes and nBu4NF as well as electron-deficient alkyl halides. In this reaction, activation of the trimethylsilyl moiety by fluoride is the key step for generating electron-rich silicate intermediates, while reduction of electron-deficient

  N,N' -Bis(trimethylsilyl)-1,4-dihydropyrazines 用作起始材料，用于在与醛和n Bu 4 NF 以及缺电子烷基卤化物结合时将烷基基团引入母体吡嗪骨架。在该反应中，氟化物对三甲基甲硅烷基部分的活化是生成富电子硅酸盐中间体的关键步骤，而缺电子烷基卤化物被1a还原产生自由基阳离子 [ 1a ]⋅ +以进一步形成 C-C 键.
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Methods of selectively forming substituted pyrazines
  申请人：R. J. Reynolds Tobacco Company

  公开号：US11091446B2

  公开（公告）日：2021-08-17

  Methods of selectively forming substituted pyrazines are provided. Methods of the present invention can include receiving a reaction solution including at least one carbon source and at least one nitrogen source, and heating the reaction solution to a reaction temperature and holding the reaction solution at the reaction temperature for a time sufficient to produce a reaction product comprising at least one substituted pyrazine. The carbon source can be selected from the group consisting of hydroxy ketone(s), sugar(s) treated with at least one buffer, and combinations thereof. Tobacco products incorporating substituted pyrazines are also provided.

  本发明提供了选择性形成取代吡嗪的方法。本发明的方法可包括接收包括至少一种碳源和至少一种氮源的反应溶液，将反应溶液加热至反应温度，并将反应溶液保持在反应温度足够长的时间，以产生包含至少一种取代吡嗪的反应产物。碳源可以选自羟基酮、用至少一种缓冲剂处理过的糖及其组合。还提供了含有取代吡嗪的烟草产品。
• Process for the preparation of 2,3,5(6) trialkyl pyrazines
  申请人：SOCIETE DES PRODUITS NESTLE S.A.

  公开号：EP0590296B1

  公开（公告）日：1995-11-02