(RS)-3-hydroxy-3-methylheptane-2,4-dione | 908334-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-3-hydroxy-3-methylheptane-2,4-dione
• 英文别名: 3-Hydroxy-3-methylheptane-2,4-dione
• CAS: 908334-40-7
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: GSSADRNAASRQSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-己二酮 在 盐酸硫胺 、 三乙胺 作用下， 以 PEG₄₀₀ 为溶剂， 以65%的产率得到(RS)-3-hydroxy-3-methylheptane-2,4-dione
  参考文献：
  名称：

  α-Diketones as acyl anion equivalents: a non-enzymatic thiamine-promoted route to aldehyde–ketone coupling in PEG400 as recyclable medium

  摘要：

  By mimicking the peculiar behavior of thiamine diphosphate-dependent acetylacetoin synthase, it has been demonstrated that thiamine hydrochloride 2a and its simple analogue thiazolium salt 2b are able to activate alpha-diketones as acyl anion equivalents in nucleophilic acylations, such as the homo-coupling of alpha-diketones and the hitherto unreported cross-coupling between a-diketones and alpha-ketoesters. These carboligation reactions were optimized under stoichiometric (2a) and catalytic conditions (2b) by using eco-friendly PEG400 as the reaction medium, thus allowing both solvent and thiazolium salt recycling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.056

文献信息

• Bacillus stearothermophilus acetylacetoin synthase: A new catalyst for C–C bond formation
  作者：Pier Paolo Giovannini、Paola Pedrini、Valentina Venturi、Giancarlo Fantin、Alessandro Medici

  DOI：10.1016/j.molcatb.2010.03.001

  日期：2010.6

  The synthesis of α-hydroxy-1,3-diketones 2 and 3 from the corresponding 1,2-diketones with Bacillus stearothermophilus ATCC2027 acetylacetoin synthase (AAS) was described. The enzyme catalyzed the condensation of the dialkyl- or alkyl-aryl-1,2-diketones 1 with the elimination of a carboxylic acid moiety. The reactions were carried out using either one diketone both acting as donor and acceptor (homo-coupling)

  描述了用嗜热脂肪芽孢杆菌ATCC2027乙酰丙酮合成酶（AAS）从相应的1,2-二酮合成α-羟基-1,3-二酮2和3。该酶催化二烷基-或烷基-芳基-1,2-二酮1的缩合并消除了羧酸部分。使用既充当供体又受主的二酮（均相偶联）或使用两种不同的反应物种（交叉偶联）进行反应。不对称二烷基-1，2-二酮1c – d的均偶联反应提供了区域异构体2（30–42％，ee 67–70％）和3的混合物（19–25％），而使用2,3-丁二酮1a，3,4仅获得1,3-二酮2a（57％），2b（60％）和2e（45％，ee 76％）-己二酮1b和1-苯基-1,2-丙二酮1e。二酮1a和1b以及1b和1e的交叉偶联反应使用不同比例的供体和受体进行。在这两种情况下，唯一的交叉偶联产物是3-乙基-3-羟基-2,4-己二酮4（62％，ee 91％）。
• FLAVORING INGREDIENTS
  申请人：Naef Regula

  公开号：US20070259088A1

  公开（公告）日：2007-11-08

  The present invention relates to a compound of formula wherein R 1 is a C 2-7 linear alkyl group. This compound can be used as flavoring ingredient, for instance to impart flavor notes of the green tea and creamy/fatty type as well as to impart a desirable mouthfeel effect.

  本发明涉及一种化合物，其化学式为其中R1是一种C2-7的直链烷基。该化合物可用作调味成分，例如赋予绿茶和奶油/脂肪类型的风味注释，以及赋予理想的口感效果。
• Chemosensory Receptor Ligand-Based Therapies
  申请人：Brown Martin R.

  公开号：US20130303466A1

  公开（公告）日：2013-11-14

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administering a composition comprising a chemosensory receptor ligand. Also provided herein are chemosensory receptor ligand compositions and methods for the preparation thereof for use in the methods of the present invention.
• US7794767B2
  申请人：——

  公开号：US7794767B2

  公开（公告）日：2010-09-14
• [EN] FLAVORING INGREDIENTS<br/>[FR] PRODUITS AROMATIQUES
  申请人：FIRMENICH & CIE

  公开号：WO2006092749A1

  公开（公告）日：2006-09-08

  [EN] The present invention relates to a compound of formula (I) wherein R¹ is a C _2-7 linear alkyl group; which can be used as flavouring ingredient, for instance to impart flavour notes of the green tea and creamy /fatty type as well as a mouthfeel effect.
  [FR] La présente invention concerne un composé selon une formule dans laquelle R¹ est un groupe alkyle linéaire C _2-7 ; qui peut être utilisé comme produit aromatique, par exemple pour donner des notes aromatiques de thé vert et de type crémeux/gras de même qu'un effet de bouche.