2-acetylthio-4-heptanone | 1006684-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-acetylthio-4-heptanone
• 英文别名: S-(4-oxoheptan-2-yl) ethanethioate
• CAS: 1006684-42-9
• 化学式: C₉H₁₆O₂S
• 分子量: 188.291
• InChiKey: BUAGALZUWDEIET-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：

  2-acetylthio-4-heptanone 在 Candida antarctica B lipase adsorbed on a macroporous acrylic resin 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 以94%的产率得到
  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：

  (E)-hept-2-en-4-one 、 硫代乙酸 反应 4.0h， 以78%的产率得到2-acetylthio-4-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

• Absolute Configurations and Sensory Properties of the Stereoisomers of a Homologous Series (C6–C10) of 2-Mercapto-4-alkanols
  作者：Anja Devenie Riegel、Christiane Kiske、Viktoriia Dudko、Iulia Poplacean、Wolfgang Eisenreich、Karl-Heinz Engel

  DOI：10.1021/acs.jafc.0c00221

  日期：2020.3.4

  addition of thioacetic acid to the respective alkenones and subsequent reduction with LiAlH4. Gas chromatographic separation of the stereoisomers was achieved using chiral stationary phases. Their absolute configurations were assigned by the correlation of 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were determined by capillary gas chromatography/olfactometry. Compared

  通过向各自的烯酮中加入硫代乙酸并随后用LiAlH 4还原获得2-巯基-4-链烷醇的同源系列（C6-C10）。使用手性固定相进行气相色谱分离立体异构体。它们的绝对构型由1 H NMR数据和酶催化的动力学拆分之间的相关性确定。气味阈值和气味质量通过毛细管气相色谱/嗅觉测定法测定。与报道的异构4-巯基-2-链烷醇的气味相比，2-巯基-4-链烷醇的同源系列缺乏果味，热带气息。构型与气味质量之间没有一致的相关性。然而，观察到的气味阈值表明了带有羟基和烷基取代基的不对称中心构型的重要性。该烷基链的长度是气味特性的主要驱动力，从刺鼻，蔬菜到泥土，蘑菇味不等。