(R)-4-mercapto-2-heptanone | 1423729-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-mercapto-2-heptanone
• 英文别名: (4R)-4-sulfanylheptan-2-one
• CAS: 1423729-54-7
• 化学式: C₇H₁₄OS
• 分子量: 146.254
• InChiKey: SMMYHWPJPFCRLH-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-庚烯-2-酮 在 lipase from porcine pancreas type II 作用下， 以 aq. phosphate buffer 为溶剂， 反应 7.5h， 生成 (R)-4-mercapto-2-heptanone 、 (S)-4-mercapto-2-heptanone
  参考文献：
  名称：

  4-巯基-2-链烷醇同源系列（C5–C10）立体异构体的分析和感官评估

  摘要：

  同源的4-巯基-2-链烷醇系列（C5-C10）用于研究立体化学对一类具有1,3-氧-硫官能度的天然存在的多官能硫醇的感官特性的影响。立体异构体是通过外消旋混合物的合成和随后的脂肪酶催化的动力学拆分而获得的。立体异构体的分析分离是通过使用手性固定相的毛细管气相色谱法（GC）实现的。通过NMR分析确定绝对构型。通过GC /嗅觉测定法进行的感官评估显示，4-巯基-2-链烷醇立体异构体的中链同系物（C7-C9）的气味阈值极小。除C5同源物外，（2 R，4 R）-配置的立体异构体。气味质量的变化主要由链长决定。对于所有同系物，4-巯基-2-链烷醇立体异构体均未显示出一致的气味品质。

  DOI：

  10.1021/acs.jafc.7b03543

文献信息

• Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives
  作者：Svenja Nörenberg、Bastian Reichardt、Verena Andelfinger、Wolfgang Eisenreich、Karl-Heinz Engel

  DOI：10.1021/jf305447e

  日期：2013.3.6

  4-Mercapto-2-heptanol, previously described in cooked bell pepper, was used to determine the impact of the stereochemistry on the sensory properties of a thiol with a 1,3-oxygen-sulfur functionality. In addition, the acetyl-derivatives 4-acetylthio-2-heptanol, 4-mercapto-2-heptyl acetate and 4-acetylthio-2-heptyl acetate were investigated. The synthesized stereoisomers were separated via capillary gas chromatography (GC) using chiral stationary phases. The GC orders of elution were determined by assigning the absolute configurations via NMR analysis in combination with lipase-catalyzed kinetic resolutions. Odor thresholds and odor properties were determined by means of GC/Olfactometry. The data revealed that the sensory properties of the investigated compounds are not only significantly influenced by the acetylation but also by the configurations of the two asymmetric centers.
• Distributions of the Stereoisomers of β-Mercaptoheptanones and β-Mercaptoheptanols in Cooked Bell Pepper (<i>Capsicum annuum</i>)
  作者：Svenja Nörenberg、Christiane Kiske、Andrea Burmann、Iulia Poplacean、Karl-Heinz Engel

  DOI：10.1021/acs.jafc.7b04336

  日期：2017.11.29

  2-Mercapto-4-heptanone, 4-mercapto-2-heptanone, and the corresponding mercaptoalcohols, previously identified in cooked red bell pepper (Capsicum annuum), were used as examples to determine the distributions of stereoisomers of naturally occurring polyfunctional thiols. The thiols were isolated using simultaneous distillation extraction and enriched by affinity chromatography. Enantioselective analysis was performed via multidimensional gas chromatography. For the studied cultivar California Wonder, the investigation of different batches of cooked red bell pepper revealed consistent ratios of the stereoisomers independent of origin and date of purchase. Quantitative estimations showed that the stereoisomers were present in cooked red bell peppers at concentrations in the range of 0.04-10.2 mu g/kg. Lower concentrations were observed in cooked green bell peppers. The change from green to red color was also accompanied by shifts in the proportions of stereoisomers in favor of the (S)-enantiomers of the mercaptoheptanones and of the (4S)-configured stereoisomers of 4-mercapto-2-heptanol.
• Analysis and Sensory Evaluation of the Stereoisomers of a Homologous Series (C5–C10) of 4-Mercapto-2-alkanols
  作者：Svenja Nörenberg、Christiane Kiske、Bastian Reichardt、Verena Andelfinger、Anne Pfeiffer、Franziska Schmidts、Wolfgang Eisenreich、Karl-Heinz Engel

  DOI：10.1021/acs.jafc.7b03543

  日期：2017.10.11

  the medium-chain homologues (C7–C9) of the 4-mercapto-2-alkanol stereoisomers. Except for the C5 homologue, the lowest odor thresholds were determined for the (2R,4R)-configured stereoisomers. The variability in odor qualities was mainly determined by the chain length. None of the 4-mercapto-2-alkanol stereoisomers showed consistent odor qualities for all homologues.

  同源的4-巯基-2-链烷醇系列（C5-C10）用于研究立体化学对一类具有1,3-氧-硫官能度的天然存在的多官能硫醇的感官特性的影响。立体异构体是通过外消旋混合物的合成和随后的脂肪酶催化的动力学拆分而获得的。立体异构体的分析分离是通过使用手性固定相的毛细管气相色谱法（GC）实现的。通过NMR分析确定绝对构型。通过GC /嗅觉测定法进行的感官评估显示，4-巯基-2-链烷醇立体异构体的中链同系物（C7-C9）的气味阈值极小。除C5同源物外，（2 R，4 R）-配置的立体异构体。气味质量的变化主要由链长决定。对于所有同系物，4-巯基-2-链烷醇立体异构体均未显示出一致的气味品质。