2,5-二甲基-3-戊基-吡嗪 | 56617-69-7

• 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-戊基-吡嗪
• 英文名称: 2,5-dimethyl-3-pentylpyrazine
• CAS: 56617-69-7
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: VJNUCPVMBFFSSP-UHFFFAOYSA-N

物化性质

• 保留指数：
  1291

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-3-戊基-吡嗪 在 双氧水 、 溶剂黄146 作用下， 生成 2,5-dimethyl-3-pentyl-pyrazine-1,4-dioxide
  参考文献：
  名称：

  Pyrazines. I. Pyrazine-N-oxides. Preparation and Spectral Characteristics¹

  摘要：

  DOI：

  10.1021/ja01528a035
• 作为产物：
  描述：

  2,5-二甲基-3-[(1E)-1-戊烯-1-基]吡嗪 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 23.0 ℃ 、303.97 kPa 条件下， 以100%的产率得到2,5-二甲基-3-戊基-吡嗪
  参考文献：
  名称：

  Zirconium-mediated reactions of alkylpyrazines and alkynes. Synthesis of highly substituted alkylpyrazines

  摘要：

  Sequential one-pot addition of alkylpyrazines, alkynes, and a proton source to a solution of Cp2Zr(Me)(THF)+ (1) in CH2Cl2 at room temperature affords (E)-alkenyl-substituted alkylpyrazines 2-10 in excellent yields. The regio- and stereoselectively observed in these reactions is similar to those observed previously for related early transition metal-mediated reactions and is ascribed to steric and Si electronic effects. Conventional synthetic organic manipulation of the alkenylpyrazines provides easy access to a variety of highly substituted alkylpyrazines including tri- and tetrasubstituted alkylpyrazines 13, 17-20, dibromoalkylpyrazine 14, bromoalkylpyrazine 15, and epoxyalkylpyrazine 16.

  DOI：

  10.1021/jo00048a038

文献信息

• Preparation of pyrazines
  申请人：SOCIETE DES PRODUITS NESTLE S.A.

  公开号：EP1357193A1

  公开（公告）日：2003-10-29

  The present invention relates to a new process for the generation of pyrazines consisting in the bioconversion of hydroxyketones with 1,2-diaminopropane. New tetrahydropyrazine derivatives as well as new dihydropyrazine derivatives with high flavour and low threshold properties are disclosed. Such pyrazines compounds exhibiting roasted and earthy aroma profiles may be used in the food and bevererage industry, especially chocolate, confectionery and coffee.

  本发明涉及一种生成吡嗪类化合物的新工艺，该工艺包括通过1,2-二氨基丙烷对羟基酮的生物转化。公开了新的四氢吡嗪衍生物以及新的二氢吡嗪衍生物，这些衍生物具有浓郁的风味和低阈值特性。这些呈现烤制和泥土香味的吡嗪化合物可用于食品和饮料行业，特别是用于巧克力、糖果和咖啡。
• Site-Selective C–H Alkylation of Diazine <i>N</i>-Oxides Enabled by Phosphonium Ylides
  作者：Prithwish Ghosh、Na Yeon Kwon、Sangil Han、Saegun Kim、Sang Hoon Han、Neeraj Kumar Mishra、Young Hoon Jung、Sang J. Chung、In Su Kim

  DOI：10.1021/acs.orglett.9b02365

  日期：2019.8.16

  The synthesis of alkylated diazine derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we describe the metal-free site-selective C–H alkylation of diazine N-oxides using phosphonium ylides that affords a variety of alkylated diazine derivatives with broad functional group tolerance. The utility of this method is showcased by the late-stage functionalization

  烷基化的二嗪衍生物的合成对于它们作为药物的实际应用和其他目的是重要的。在本文中，我们描述了使用磷鎓叶立德的无金属位点选择性地使二嗪N-氧化物进行CH烷基化，该phospho鎓可提供具有宽泛的官能团耐受性的各种烷基化的二嗪衍生物。该方法的实用性通过市售药物（例如缬尼克兰）的后期功能化得以展示。值得注意的是，吡嗪N-氧化物的顺序C–H烷基化可完全合成含吡嗪的天然产物paenibacillin A，突出了该方法的重要性。
• Synthesis and pyrolysis of two flavor precursors of oct-1-en-3-yl methylpyrazinecarboxylates
  作者：Miao Lai、Xiaoming Ji、Tao Tao、Yuanyuan Shan、Pengfei Liu、Mingqin Zhao

  DOI：10.1007/s10973-016-6083-5

  日期：2017.6

  To rich flavor additive species of pyrazines, two new compounds of 3,6-dimethyl-2,5-pyrazinedicarboxylic acid 1-octen-3-yl ester (DMPOE) and 3,5,6-trimethyl-2-pyrazinecarboxylic acid 1-octen-3-yl ester (TMPOE) were synthesized by KMnO4 oxidation, acylating chlorination and esterification reaction, in which tetramethylpyrazine and 1-octen-3-ol were used as initial materials. Thermogravimetry (TG), differential scanning calorimeter (DSC) and pyrolysis–gas chromatography/mass spectrometry (Py–GC/MS) were conducted to investigate the thermal degradation behaviors of DMPOE and TMPOE. TG–DTG results indicated that the T p of DMPOE and TMPOE with the largest mass loss rate was at 310 and 250 °C, respectively. The T peak of DMPOE and TMPOE showed by DSC curves was 301.8 and 260.0 °C, respectively. Py–GC/MS was performed to benefit the simulation of cigarette burning conditions, and the results indicated that DMPOE and TMPOE could release specific flavors of 1-octen-3-ol and diversified alkylpyrazines. Furthermore, the thermal degradation mechanisms of the flavor precursors of DMPOE and TMPOE were discussed. The study on the thermal behavior of these two methylpyrazinecarboxylates would provide theoretical basis for their application in tobacco.

  为了丰富吡嗪类香料添加剂的种类，通过 KMnO4 氧化、酰化氯化和酰化氯化反应合成了 3,6-二甲基-2,5-吡嗪二羧酸 1-辛烯-3-基酯（DMPOE）和 3,5,6-三甲基-2-吡嗪二羧酸 1-辛烯-3-基酯（TMPOE）两种新化合物、以四甲基吡嗪和 1-辛烯-3-醇为初始原料，通过 KMnO4 氧化、酰化氯化和酯化反应合成了 3,6-二甲基-2,5-吡嗪二羧酸 1-辛烯-3-基酯（DMPOE）和 3,5,6-三甲基-2-吡嗪二羧酸 1-辛烯-3-基酯（TMPOE）。采用热重法（TG）、差示扫描量热仪（DSC）和热解-气相色谱/质谱法（Py-GC/MS）研究了 DMPOE 和 TMPOE 的热降解行为。TG-DTG结果表明，质量损失率最大的DMPOE和TMPOE的T峰分别位于310和250 ℃。DSC 曲线显示 DMPOE 和 TMPOE 的 T 峰分别为 301.8 和 260.0 ℃。为了模拟香烟燃烧条件，研究人员进行了 Py-GC/MS，结果表明 DMPOE 和 TMPOE 能释放出特定的 1-辛烯-3-醇和多种烷基吡嗪。此外，还讨论了 DMPOE 和 TMPOE 香味前体的热降解机制。对这两种甲基吡嗪羧酸盐热行为的研究将为它们在烟草中的应用提供理论依据。
• The Action of Organolithium Compounds on 2,5-Dimethylpyrazine. II¹
  作者：Bernard Klein、Paul E. Spoerri

  DOI：10.1021/ja01150a519

  日期：1951.6
• Novel heterocyclic carbothioamides, compositions containing them, their preparation and use
  申请人：ELI LILLY AND COMPANY

  公开号：EP0002938B1

  公开（公告）日：1982-05-12

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