2-(2-oxopropyl)hexanoic acid | 26817-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-(2-oxopropyl)hexanoic acid
• 英文别名: (+/-)-2-acetonyl-hexanoic acid；(+/-)-2-Acetonyl-hexansaeure
• CAS: 26817-75-4
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: UAXYZEFHBYNQTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-oxopropyl)hexanoic acid 在 溴 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 2-(1,3-Dibromo-2-oxo-propyl)-hexanoic acid
  参考文献：
  名称：

  Revisiting AI-2 Quorum Sensing Inhibitors: Direct Comparison of Alkyl-DPD Analogues and a Natural Product Fimbrolide

  摘要：

  Quorum sensing (QS) systems have been discovered in a wide variety of bacteria, and mediate both intra- and interspecies communication. The AI-2-based QS system represents the most studied of these proposed interspecies systems and has been shown to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the study of unknown AI-2-based QS systems and the potential treatment of bacterial infections. The fimbrolide class of natural products has exhibited excellent inhibitory activity against AI-2-based QS and as such may be considered the "gold standard" of AI-2 inhibitors. Thus, we sought to include a fimbrolide as a control compound for our recently developed alkyl-DPD panel of AI-2 modulators. Herein, we present a revised synthesis of a commonly studied fimbrolide as well as a direct comparison between the fimbrolide and alkyl-DPD analogues. We demonstrate that our alkyl-DPD analogues are more potent inhibitors of QS in both Vibrio harveyi and Salmonella typhimurium, the two organisms with defined AI-2 QS systems, and in doing so call into question the widely accepted use of fimbrolide-derived compounds as the "gold standard" of AI-2 inhibition.

  DOI：

  10.1021/ja9066783
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 mercury(II) sulfate 作用下， 生成 2-(2-oxopropyl)hexanoic acid
  参考文献：
  名称：

  Colonge; Gelin, Bulletin de la Societe Chimique de France, 1954, p. 797

  摘要：

  DOI：

文献信息

• Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
  作者：Toshiro Harada、Shinya Adachi、Fumi Tanaka、Kazuya Watanabe、Atsushi Watada

  DOI：10.1055/s-0029-1218821

  日期：2010.8

  allo-Threonine-derived oxazaborolidinone (OXB) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic α,β-unsaturated ketones to give the products in high yields and with high enantioselectivities. With 5-10 mol% of the OXB catalyst, enantioselectivities of up to 94% ee could be achieved for a variety of substrates. The use of N,N-dimethylaniline (2.5-10 mol%) as an additive

  同种异体-苏氨衍生oxazaborolidinone（OXB）催化呋喃和吲哚用简单的无环α，β不饱和酮的弗瑞德-克莱福特烷基化，得到产物以高产率和高对映选择性。使用5-10 mol％的OXB催化剂，对于多种底物，可以实现高达94％ee的对映选择性。已发现使用N，N-二甲基苯胺（2.5-10mol％）作为添加剂对于对映选择性是必不可少的。根据质子催化的外消旋途径的阻滞讨论了添加剂的作用，这阻碍了Friedel-Crafts反应的对映选择性。 不对称催化-烯酮-Friedel-Crafts反应-呋喃-吲哚
• METHOD TO PRODUCE AND RECOVER LEVULINIC ACID AND/OR GAMMA-VALEROLACTONE FROM AQUEOUS SOLUTIONS USING ALKYLPHENOLS
  申请人：Dumesic James

  公开号：US20120302764A1

  公开（公告）日：2012-11-29

  A method to produce levulinic acid (LA) and γ-valerolactone (GVL) from biomass-derived cellulose by selective extraction of LA by alkylphenol (AP) and hydrogenation of LA, in which mineral acid used in the method is recycled and the final concentration of GVL is increased by successive extraction/hydrogenation steps to allow for effective separation by distillation.

  一种从生物质来源的纤维素中生产左旋肉碱酸（LA）和γ-戊内酯（GVL）的方法，通过使用烷基酚（AP）选择性提取LA，并对LA进行氢化。该方法中使用的矿酸被循环利用，并通过连续的提取/氢化步骤增加GVL的最终浓度，以便通过蒸馏进行有效分离。
• METHOD TO PRODUCE, RECOVER AND CONVERT FURAN DERIVATIVES FROM AQUEOUS SOLUTIONS USING ALKYLPHENOL EXTRACTION
  申请人：Dumesic James

  公开号：US20120302765A1

  公开（公告）日：2012-11-29

  Described is a catalytic process for converting biomass to furan derivatives (e.g., furfural, furfuryl alcohol, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase containing an alkylphenol. The process provides a cost-effective route for producing furfural, furfuryl alcohol, levulinic acid hydroxymethylfurfural, γ-valerolactone, and the like. The products formed are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.

  描述了一种催化过程，将生物质转化为呋喃衍生物（如糠醛、糠醇等），使用一个含有反应性水相和含有烷基酚的有机萃取相的两相反应器。该过程提供了一条经济高效的生产糠醛、糠醇、乙醇酸、羟甲基呋喃、γ-戊内酯等产品的途径。所形成的产品可用作生产聚合物的附加值中间体，作为柴油燃料的前体，以及作为燃料添加剂。
• Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones
  作者：Anthony J. Manny、Staffan Kjelleberg、Naresh Kumar、Rocky de Nys、Roger W. Read、Peter Steinberg

  DOI：10.1016/s0040-4020(97)10034-5

  日期：1997.11

  through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation occurs

  描述了由烷基取代的乙酰丙酸衍生物通过溴化和酸促进的内酯化合成乙基，丁基，己基和十二烷基取代的溴化物。使用乙酰丙酸作为模型，研究了潜在的反应，并讨论了改变溴化条件和改变酸浓度对产物分布的影响。二溴化在CHCl 3中进行得最好，在无EtOH的CHCl 3中进行，而不会形成酯。在98–100％H 2 SO 4中伴随氧化发生环化反应，但在100％H 2 SO 4中产生环戊内酯的产率最高。还描述了相关的贝克雷利物质的形成。
• NEW SYNTHESIS OF γ-KETO ACIDS FROM NITROOLEFINS AND CARBOXYLIC ACID DIANIONS
  作者：Masaaki Miyashita、Ryuji Yamaguchi、Akira Yoshikoshi

  DOI：10.1246/cl.1982.1505

  日期：1982.10.5

  As a convenient synthetic method of γ-keto acids, oxoalkylation of carboxylic acids with nitroolefins was examined. Carboxylic acid dianions reacted with conjugated nitroolefins at low temperature (−100°C) and a variety of γ-keto acids were obtained on acidic workup in moderate to good yields.

  作为γ-酮酸的一种方便的合成方法，研究了羧酸与硝基烯烃的氧烷基化。羧酸二价阴离子在低温 (-100°C) 下与共轭硝基烯烃反应，并在酸性处理中以中等至良好的产率获得各种 γ-酮酸。