4-acetylthio-2-heptanone | 1006684-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 4-acetylthio-2-heptanone
• 英文别名: 4-Acetylthio-2-heptanone；S-(2-oxoheptan-4-yl) ethanethioate
• CAS: 1006684-35-0
• 化学式: C₉H₁₆O₂S
• 分子量: 188.291
• InChiKey: ZZKLTMJNBHTJQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetylthio-2-heptanone 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 4-mercapto-2-heptanone
  参考文献：
  名称：

  Distributions of the Stereoisomers of β-Mercaptoheptanones and β-Mercaptoheptanols in Cooked Bell Pepper (Capsicum annuum)

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.7b04336
• 作为产物：
  描述：

  反式-3-庚烯-2-酮 、 硫代乙酸 反应 4.0h， 以85%的产率得到4-acetylthio-2-heptanone
  参考文献：
  名称：

  红灯笼椒（辣椒）的同时蒸馏萃取提取物中的新的挥发性挥发性含硫成分。

  摘要：

  通过同时蒸馏-萃取（SDE，Likens-Nickerson）制备红甜椒（Capsicum annuum）的提取物。除了已知的（3 E）-3-庚-2-酮（1）外，不饱和C9-酮1-壬烯-4-酮（2），（2 E）-2-壬烯-4-酮（3）和（2 E，5 E）-2,5-nonadien-4-one（4），2-甲氧基-3-异丁基吡嗪（5）和庚烷-2-硫醇（6），我们确定了19新硫醇（脂族饱和和不饱和硫醇14-16和22-27，巯基酮12和13，巯基醇17、18和30，二硫醇19和28，甲硫醇20和21 ，以及噻吩-硫醇31）和两个新的二噻吩10和29。它们在结构上均与不饱和C7-和C9-酮1-4相关。使用Affi-Gel 501（对氨基苯酚）富集了游离硫醇-乙酸汞接枝在琼脂糖凝胶上）。

  DOI：

  10.1021/jf072493y

文献信息

• 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。
• 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.
• New Volatile Sulfur-Containing Constituents in a Simultaneous Distillation−Extraction Extract of Red Bell Peppers (Capsicum annuum)
  作者：Regula Naef、Alain Velluz、Alain Jaquier

  DOI：10.1021/jf072493y

  日期：2008.1.1

  mercapto-alcohols 17, 18, and 30, the dithiols 19 and 28, the methylthio-thiols 20 and 21, and the thiophene-thiol 31) and the two new dithiolanes 10 and 29. All of them are structurally related to the unsaturated C7- and C9-ketones 1- 4. The free thiols were enriched using Affi-Gel 501 ( p-aminophenyl-mercuric acetate grafted on an agarose gel). The new compounds were confirmed by syntheses and were organoleptically

  通过同时蒸馏-萃取（SDE，Likens-Nickerson）制备红甜椒（Capsicum annuum）的提取物。除了已知的（3 E）-3-庚-2-酮（1）外，不饱和C9-酮1-壬烯-4-酮（2），（2 E）-2-壬烯-4-酮（3）和（2 E，5 E）-2,5-nonadien-4-one（4），2-甲氧基-3-异丁基吡嗪（5）和庚烷-2-硫醇（6），我们确定了19新硫醇（脂族饱和和不饱和硫醇14-16和22-27，巯基酮12和13，巯基醇17、18和30，二硫醇19和28，甲硫醇20和21 ，以及噻吩-硫醇31）和两个新的二噻吩10和29。它们在结构上均与不饱和C7-和C9-酮1-4相关。使用Affi-Gel 501（对氨基苯酚）富集了游离硫醇-乙酸汞接枝在琼脂糖凝胶上）。
• 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.