2-羟基-3-己酮 | 54073-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基-3-己酮
• 英文名称: 2-Hydroxy-hexan-3-one
• 英文别名: 2-hydroxy-3-hexanone；2-hydroxyhexan-3-one；3-hexanon-2-ol；2-Hydroxy-hexan-3-on
• CAS: 54073-43-7
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: ZWBUSAWJHMPOEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  60-61 °C(Press: 11 Torr)
• 密度：
  0.9443 g/cm3
• 保留指数：
  895.5

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  2-羟基-3-己酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 己烷-2,3-二醇
  参考文献：
  名称：

  The male pheromone of the old house borerHylotrupes bajulus (L.) (Coleoptera: Cerambycidae): Identification and female response

  摘要：

  We report here the identification of the long-range, male-produced sex pheromone of the Old house borer Hylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol.In wind tunnel bioassays we tested the influence of these male-specific compounds from the prothoracal glands on the behaviour of unmated and mated females. Specific behavioural sequences of the tested females (activity, running behaviour, searching, cleaning, flying, extension of ovipositor) were recorded. Unmated females were attracted by male beetles, headspace extracts of males, synthetic blends of the major pheromone compounds as well as by the components (3R)-3-hydroxy-2-hexanone, and the diastereomeric diols. Hexane, female beetles and 2,3-hexanedione did not attract unmated females. The reactions of mated females to male beetles and headspace samples did not differ significantly from those of the controls.The results of the bioassays show that the two-stage premating behaviour is initiated by emission of a long-range sex pheromone from the male prothoracal glands, which functions as an activator, attractant, and possibly aphrodisiac for unmated females.

  DOI：

  10.1007/bf01931111
• 作为产物：
  描述：

  2-乙酰氧基-己-4-烯-3-酮 在 sodium hydroxide 、 乙醇 、 铂 作用下， 生成 2-羟基-3-己酮
  参考文献：
  名称：

  Nasarow; Kugatowa; Mosolis, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2635,2638

  摘要：

  DOI：

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。
• Pyrazine Biosynthesis in Corynebacterium glutamicum
  作者：Jeroen S. Dickschat、Susanne Wickel、Christoph J. Bolten、Thorben Nawrath、Stefan Schulz、Christoph Wittmann

  DOI：10.1002/ejoc.201000155

  日期：2010.5

  the acetoin precursor (S)-2-acetolactate into the pathway intermediate (R)-2,3-dihydroxy-3-methylbutanoate to the branched amino acids. This mutant requires valine, leucine, and isoleucine for growth and produces significantly higher amounts and more different compounds of the acyloin and pyrazine classes. Gene deletion of the acetolactate synthase (AS) resulted in a mutant that is not able to convert

  使用 CLSA 技术（闭环汽提装置）收集谷氨酸棒杆菌释放的挥发性化合物，并通过 GC-MS 进行分析。顶空提取物包含几种丙烯酰和吡嗪，通过合成或与商业标准的比较进行鉴定。用 [2H7] 乙偶姻喂食实验导致标记掺入到三甲基吡嗪和四甲基吡嗪中。构建了几个靶向初级代谢基因的缺失突变体，以详细阐明吡嗪的生物合成途径。酮醇酸还原异构酶的缺失突变体无法将乙偶姻前体 (S)-2-乙酰乳酸转化为途径中间体 (R)-2,3-二羟基-3-甲基丁酸，进而转化为支链氨基酸。这个突变体需要缬氨酸、亮氨酸、和异亮氨酸用于生长并产生显着更高数量和更多不同的 acyloin 和吡嗪类化合物。乙酰乳酸合酶 (AS) 的基因缺失导致无法将丙酮酸转化为 (S)-2-乙酰乳酸的突变体。该突变体还需要支链氨基酸，并且可能仅从缬氨酸通过以相反顺序运行的缬氨酸生物合成途径产生非常少量的吡嗪。构建了完全不产生任何吡嗪的 ΔASΔKR 双突变体。这些结果为通过
• Reduction of 1,2-diketones with titanium tetraiodide: a simple approach to α-hydroxy ketones
  作者：Ryuuichirou Hayakawa、Tetsuya Sahara、Makoto Shimizu

  DOI：10.1016/s0040-4039(00)01385-x

  日期：2000.10

  1,2-Diketones are readily reduced with titanium tetraiodide to give α-hydroxy ketones in good to excellent yields. Regioselectivity on the reduction of unsymmetrical substrates is also discussed.

  用四碘化钛容易地还原1,2-二酮，从而以良好或优异的收率得到α-羟基酮。还讨论了还原非对称底物时的区域选择性。
• Process for making n-aryl-anthranilic acids and their derivatives
  申请人：——

  公开号：US20040039208A1

  公开（公告）日：2004-02-26

  The present invention relates to a process for the preparation of N-arylanthranilic acids, and a process for the preparation of N-aryl anthranilic esters, amides, and hydroxamic esters.

  本发明涉及一种制备N-芳基蒽酰胺酸的方法，以及制备N-芳基蒽酰酯、酰胺和羟肟酯的方法。
• Chemoenzymatic Synthesis of Aroma Active 5,6-Dihydro- and Tetrahydropyrazines from Aliphatic Acyloins Produced by Baker's Yeast
  作者：Toshinari Kurniadi、Rachid Bel Rhlid、Laurent-Bernard Fay、Marcel-Alexandre Juillerat、Ralf Günter Berger

  DOI：10.1021/jf0261809

  日期：2003.5.1

  Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines

  以面包酵母的整个细胞为催化剂，通过脂肪族醛和2-酮羧酸的生物转化，产生了二十五个酰化甘油。首次合成了其中的六种酰基辅酶，并对其进行了初步鉴定。随后在温和的条件下与1,2-丙二胺发生化学反应，导致形成了十三种5,6-二氢吡嗪和六种四氢吡嗪。对它们的气味质量进行了评估，并估计了它们的气味阈值。在这些吡嗪衍生物中，2-乙基-3,5-二甲基-5,6-二氢吡嗪（烤，坚果，0.002 ng / L空气），2,3-二乙基-5-甲基-5,6-二氢吡嗪（烤，空气中的浓度为0.004 ng / L）和2-乙基-3,5-二甲基四氢吡嗪（面包类面包皮，空气中的浓度为1.9 ng / L）是气味最强烈的活性化合物。