(S)-3-acetylthiocycloheptanone | 1370608-00-6

• 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: (S)-3-acetylthiocycloheptanone
• 英文别名: S-[(1S)-3-oxocycloheptyl] ethanethioate
• CAS: 1370608-00-6
• 化学式: C₉H₁₄O₂S
• 分子量: 186.275
• InChiKey: ZQPVESMHQQGOLS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  2-环庚烯-1-酮 、 硫代乙酸 在 N-[3,5-双（三氟甲基）苯基]-N''-[（8α，9S）-6''-甲氧基七氢呋喃-9-基]脲 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (R)-3-acetylthiocycloheptanone 、 (S)-3-acetylthiocycloheptanone
  参考文献：
  名称：

  Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst

  摘要：

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.02.052

文献信息

• Analytical and Sensory Characterization of the Stereoisomers of 3-Mercaptocycloalkanones and 3-Mercaptocycloalkanols
  作者：Motoko Wakabayashi、Hidehiko Wakabayashi、Anja Devenie Riegel、Wolfgang Eisenreich、Karl-Heinz Engel

  DOI：10.1021/acs.jafc.0c03113

  日期：2020.7.8

  (chain lengths C5–C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH4, respectively. The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds

  3-巯基环烷酮和3-巯基环烷醇（链长为C5-C7）是通过将硫代乙酸分别添加到各自的2-环烯-1-酮中并随后通过酶介导的水解和用LiAlH 4还原而获得的。通过使用手性固定相的毛细管气相色谱法分离立体异构体。根据1确定其配置1 H NMR数据和酶催化的动力学拆分。气味阈值和气味质量通过毛细管气相色谱/嗅觉法评估。与类似的无环4-巯基-2-链烷酮和4-巯基-2-链烷醇相比，环状多官能硫醇缺乏果香，热带香气。感觉到的气味特性从煮熟，烤制的蔬菜和肉类到洋葱相关的香精不等。3-巯基环烷酮对映异构体的气味阈值主要受其环的大小而不是其构型的影响。对于3-巯基环烷醇，具有硫醇基的立体异构中心的（S）构型和带有羟基的第二不对称中心的相对构型对于低气味阈值很重要。
• Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst
  作者：Nirmal K. Rana、Rajshekhar Unhale、Vinod K. Singh

  DOI：10.1016/j.tetlet.2012.02.052

  日期：2012.4

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.