2,5-dimethyl-3-(3-methylbutyl)pyrazine-1-oxide | 183021-24-1

• 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-(3-methylbutyl)pyrazine-1-oxide
• 英文别名: 2,5-Dimethyl-3-(3-methylbutyl)-1-oxidopyrazin-1-ium
• CAS: 183021-24-1
• 化学式: C₁₁H₁₈N₂O
• 分子量: 194.277
• InChiKey: YKEGTDPIDHGIAV-UHFFFAOYSA-N

物化性质

• 沸点：
  345.1±37.0 °C(Predicted)
• 密度：
  1.02±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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-3-(3-methylbutyl)pyrazine-1-oxide 在 乙酸酐 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 9.0h， 以108 mg的产率得到2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine
  参考文献：
  名称：

  The Discovery of 2-Hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: A Semiochemical in Orchid Pollination

  摘要：

  Drakaea livida (Orchidaceae) is pollinated by sexual deception of the wasp Zaspilothynnus nigripes (Thynnidae). It is shown that the orchid emits the same compound, 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine, that females emit when calling for mates. This novel pyrazine was isolated and identified by GC-EAD and GC-MS and confirmed by synthesis. This compound may represent the first known case of pyrazines as sex pheromones in Hymenoptera.

  DOI：

  10.1021/ol300864u
• 作为产物：
  描述：

  3-氯-2,5-二甲基吡嗪 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 2,5-dimethyl-3-(3-methylbutyl)pyrazine-1-oxide
  参考文献：
  名称：

  吡嗪的研究。31 †镍与二烷基锌的交叉偶联反应将氯吡嗪N-氧化物烷基化

  摘要：

  将3-氯-2,5-二甲基吡嗪1-氧化物与二烷基锌试剂交叉偶联，形成3-烷基-2,5-二甲基吡嗪1-氧化物。该反应是通过催化1,3-双（二苯基膦基）丙烷镍（II）氯化物实现的，并研究了最佳结果。

  DOI：

  10.1002/jhet.5570330408

文献信息

• Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones
  作者：Nobuhiro Sato、Tomoyuki Matsuura

  DOI：10.1039/p19960002345

  日期：——

  The synthesis of trialkylpyrazines having methyl groups on C-2 and C-5 is described, which is completed by the cross-coupling reaction of 2-chloro-3,6-dimethylpyrazine with dialkylzinc in the presence of [1,3-bis(diphenylphosphino)propane] nickel(II) chloride. Similarly, 2,5-diisobutyl-, -diisopropyl- and -di-sec-butyl-3-methylpyrazines are prepared from the corresponding dialkyl chloropyrazines. The dimethyl products are acylated with an α-keto acid under the Minisci radical conditions providing 2-acyl-5-alkyl-3,6-dimethylpyrazines. Several compounds obtained in this study prove to be active as components of pheromones in ants.

  本文描述了具有C-2和C-5位甲基的三烷基吡嗪的合成方法，该合成通过2-氯-3,6-二甲基吡嗪与二烷基锌在[1,3-双(二苯基膦基)丙烷]镍(II)氯化物的催化下进行交叉耦合反应完成。类似地，从相应的二烷基氯吡嗪制备了2,5-二异丁基-、二异丙基-和二仲丁基-3-甲基吡嗪。二甲基产物通过Minisci自由基条件下与α-酮酸的酰化反应，得到了2-酰基-5-烷基-3,6-二甲基吡嗪。本研究中得到的几种化合物证实作为蚂蚁信息素的组成部分具有活性。
• Studies on pyrazines.<b>31</b>Alkylation of chloropyrazine<i>N</i>-oxides by nickel-catalyzed cross-coupling reaction with dialkylzincs
  作者：Nobuhiro Sato、Tomoyuki Matsuura

  DOI：10.1002/jhet.5570330408

  日期：1996.7

  3-Chloro-2,5-dimethylpyrazine 1-oxide underwent cross-coupling with dialkylzinc reagents forming 3-alkyl-2,5-dimethylpyrazine 1-oxides. The reaction was realized by catalytic 1,3-bis(diphenylphosphino)-propane nickel(II) chloride and the optimum results were examined.

  将3-氯-2,5-二甲基吡嗪1-氧化物与二烷基锌试剂交叉偶联，形成3-烷基-2,5-二甲基吡嗪1-氧化物。该反应是通过催化1,3-双（二苯基膦基）丙烷镍（II）氯化物实现的，并研究了最佳结果。
• The Discovery of 2-Hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: A Semiochemical in Orchid Pollination
  作者：Björn Bohman、Lynne Jeffares、Gavin Flematti、Ryan D. Phillips、Kingsley W. Dixon、Rod Peakall、Russell A. Barrow

  DOI：10.1021/ol300864u

  日期：2012.5.18

  Drakaea livida (Orchidaceae) is pollinated by sexual deception of the wasp Zaspilothynnus nigripes (Thynnidae). It is shown that the orchid emits the same compound, 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine, that females emit when calling for mates. This novel pyrazine was isolated and identified by GC-EAD and GC-MS and confirmed by synthesis. This compound may represent the first known case of pyrazines as sex pheromones in Hymenoptera.