2,5-二甲基-3-(3-甲基丁基)吡嗪 | 18433-98-2

• 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-(3-甲基丁基)吡嗪
• 英文名称: 2,5-dimethyl-3-(3-methylbutyl)pyrazine
• 英文别名: 3,6-dimethyl-2-(3-methylbutyl)pyrazine；2,5-dimethyl-3-isopentylpyrazine；3-Isopentyl-2,5-dimethylpyrazine；2,5-dimethyl-3-isoamylpyrazine；2,5-dimethyl-3-(3-methyl-butyl)-pyrazine；2,5-Dimethyl-3-(3-methylbutyl)pyrazin
• CAS: 18433-98-2
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: WWAYKGYKYHEINT-UHFFFAOYSA-N

物化性质

• 沸点：
  242.0±35.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)
• LogP：
  2.829 (est)
• 保留指数：
  1295;1296;1289;1296;1304.3

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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-(3-甲基丁基)吡嗪 在 乙酸酐 、 溶剂黄146 作用下， 反应 9.0h， 生成 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 2,5-二甲基-3-(3-甲基丁基)吡嗪
  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。
• Furfuryl propyl disulfide as a flavoring agent and methods for preparing and using same
  申请人：——

  公开号：US20020110628A1

  公开（公告）日：2002-08-15

  This invention pertains to a method for flavoring an ingestible composition with a flavoring agent, furfuryl propyl disulfide, in organoleptically purified form, unaccompanied by substances of natural origin present in cooked beef and onions. The flavoring agent may be used in a wide variety of ingestible vehicles to augment or enhance the aroma or taste of foodstuffs, particularly roasted nut, roasted meat, beef broth, black pepper, onion, fine herbs, omelet, and cooked onion omelet flavored foodstuffs. The present invention also pertains to an ingestible composition comprising an ingestible vehicle and an organoleptically effective amount of the purified flavoring agent. The present invention also pertains to furfuryl propyl disulfide represented by the formula, (2-Furan-CH 2 SSCH 2 CH 2 CH 3 ), in purified form, unaccompanied by substances of natural origin present in cooked beef and onions, and to methods for preparing furfuryl propyl disulfide.

  本发明涉及一种用味道剂味化可食用组合物的方法，所述味道剂为味觉上纯化的呋喃基丙基二硫化物，不含烹煮牛肉和洋葱时存在的天然物质。该味道剂可用于各种可食用载体中，以增强或提高食物的香气或口感，特别是烤坚果、烤肉、牛肉汤、黑胡椒、洋葱、香料、煎蛋和煮洋葱煎蛋调味食品。本发明还涉及一种包含可食用载体和纯化的味道剂的味道组合物。本发明还涉及用公式表示的呋喃基丙基二硫化物（2-呋喃-CH2SSCH2CH2CH3）的纯化形式，不含烹煮牛肉和洋葱时存在的天然物质，以及制备呋喃基丙基二硫化物的方法。
• 1-Ethoxy ethyl acetate and uses thereof for augmenting or enhancing the aroma or taste of consumable materials
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0048545A2

  公开（公告）日：1982-03-31

  Described for use in foodstuffs, chewing gums, toothpastes, medicinal products flavor and aromas, smoking tobacco flavor and aroma and perfume, cologne and perfumed article aroma augmenting, modifying, enhancing and imparting compositions and as foodstuffs, chewing gums, toothpastes, medicinal products, tobacco, perfume and perfumed article and cologne aroma imparting materials are mixtures of 1-ethoxy-1-ethanol acetate having the structure: (also hereinafter referred to as "E") and acetaldehyde (also hereinafter referred to as "A"), the range of weight ratios, E:A being from 50:50 down to 5:95.

  所述用于食品、口香糖、牙膏、药用产品风味和香气、烟草风味和香气以及香水、古龙水和香水制品香气增强、改良、提高和赋予的组合物，以及作为食品、口香糖、牙膏、药用产品、烟草、香水和香水制品以及古龙水香气赋予材料的具有以下结构的 1-乙氧基-1-乙醇醋酸酯（以下也称为 "E"）和乙醛（以下也称为 "A"）的混合物： (以下简称 "E"）和乙醛（以下简称 "A"）的混合物，E:A 的重量比范围从 50:50 到 5:95。
• Use of 1-ethoxyethyl acetate for augmenting or enhancing the aroma or taste of consumable materials
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0046072A2

  公开（公告）日：1982-02-17

  Described for use in foodstuffs, chewing gums, toothpastes, medicinal products flavor and aromas, smoking tobacco flavor and aroma and perfume, cologne and perfumed article aroma augmenting, modifying, enhancing and imparting compositions and as foodstuffs, chewing gums, toothpastes, medicinal products, tobacco, perfume and perfumed article and cologne aroma imparting materials is 1-ethoxy-1-ethanol acetate having the structure:

  所述用于食品、口香糖、牙膏、药用产品风味和香气、烟草风味和香气以及香水、古龙水和香水制品香气增强、改良、提高和赋予的组合物，以及作为食品、口香糖、牙膏、药用产品、烟草、香水和香水制品以及古龙水香气赋予材料的 1-乙氧基-1-乙醇醋酸酯具有以下结构：
• Norbornyl pyridine derivatives, their production and compositions comprising them
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0154844A1

  公开（公告）日：1985-09-18

  Described are norbornyl pyridine derivatives defined according to the generic structure: wherein R5, R5', R5", R5"' and R5"" each represents hydrogen or methyl with the proviso that at least four of R5, R5', R5". R5"' and Rs"" represent hydrogen; wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein the pyridinyl moiety is bonded to the norbornyl moiety at the 2' position of the norbornyl moiety and at either the 2 or the 4 position of the pyridinyl moiety as well as organoleptic uses thereof in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, chewing tobaccos, medicinal products, perfume compositions, colognes and perfumed articles including, but not limited to solid or liquid anionic, cationic, zwitterionic and nonionic detergents, cosmetic compositions, fabric softener compositions, fabric softener articles, hair preparations, and perfumed polymers. Also described are processes for preparing such compounds comprising reacting vinyl pyridines defined according to the structure: wherein one of R1 or R2 is hydrogen and the other of R1 or R2 is vinyl with a bicyclopentadiene derivative defined according to the structure: wherein R3, R3', R3", R3"' and R3"' each represents hydrogen or methyl with the proviso that at least four of R3, R3', R3", R3"' and R3"' represent hydrogen and wherein R4, R4', R4", R4"' and R4"' each represents hydrogen or methyl with at least four of R4, R4', R4", R4"' and R4"' representing hydrogen and then as desired hydrogenating the resulting product.

  所描述的是根据通用结构定义的降冰片基吡啶衍生物： 其中 R5、R5'、R5"、R5"'和 R5""各自代表氢或甲基，但 R5、R5'、R5"'和 R5""中至少有四个代表氢。R5"' 和 Rs"" 代表氢；其中虚线代表碳-碳单键或碳-碳双键，吡啶基在降冰片烷基的 2'位和吡啶基的 2 或 4 位上与降冰片烷基键合、口香糖、牙膏、嚼用烟草、医药产品、香水组合物、古龙水和加香物品，包括但不限于固体或液体阴离子、阳离子、齐聚离子和非离子洗涤剂、化妆品组合物、织物柔软剂组合物、织物柔软剂物品、头发制剂和加香聚合物。此外，还描述了制备此类化合物的工艺，包括使根据以下结构定义的乙烯基吡啶发生反应： 其中 R1 或 R2 中的一个是氢，R1 或 R2 中的另一个是乙烯基与根据结构定义的双环戊二烯衍生物反应： 其中 R3、R3'、R3"、R3"'和 R3"'各自代表氢或甲基，但 R3、R3'、R3"、R3"'和 R3"'中至少有四个代表氢；其中 R4、R4'、R4"、R4"'和 R4"'各自代表氢或甲基，但 R4、R4'、R4"、R4"'和 R4"'中至少有四个代表氢，然后根据需要将所得产物氢化。

表征谱图