3-(methylthio)octane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(methylthio)octane
• 英文别名: 3-Methylsulfanyloctane
• 化学式: C₉H₂₀S
• 分子量: 160.324
• InChiKey: KVBRMLKEFOAMID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-辛醇 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-(methylthio)octane
  参考文献：
  名称：

  Structure–Odor Correlations in Homologous Series of Alkanethiols and Attempts To Predict Odor Thresholds by 3D-QSAR Studies

  摘要：

  Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,?-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structureactivity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.

  DOI：

  10.1021/jf506135c

文献信息

• Amidothiol derivatives
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0021637A1

  公开（公告）日：1981-01-07

  Amidothiol derivatives have the formula wherein: R represents an alkyl, alk-2 to 6 - enyl, phenylalkyl, phenyl or heterocyclic group optionally substituted by one or more functional groups inert to electrochemical oxidation: R1, R2, R3 and R4 independently represent hydrogen or substituent groups, and r5 represents alkyl, phenylalkyl or phenyl. The derivatives are useful in the preparation of pharmaceutically active compounds and dyestuffs and have herbicidal and/or antibacterial activity. The compounds can be prepared by electrochemical oxidation of a corresponding organic disulphide in the presence of the corresponding alkene and the corresponding organic nitrite, and treatment of the reaction product with water.

  酰胺硫醇衍生物的化学式为 其中 R 代表烷基、烷-2-6-烯基、苯基烷基、苯基或杂环基团，可任选被一个或多个电化学氧化惰性官能团取代： R1、R2、R3 和 R4 分别代表氢或取代基，r5 代表烷基、苯基烷基或苯基。这些衍生物可用于制备医药活性化合物和染料，并具有除草和/或抗菌活性。这些化合物的制备方法是：在相应的烯烃和相应的有机亚硝酸盐存在下，对相应的有机二硫化物进行电化学氧化，然后用水处理反应产物。
• Structure–Odor Correlations in Homologous Series of Alkanethiols and Attempts To Predict Odor Thresholds by 3D-QSAR Studies
  作者：Johannes Polster、Peter Schieberle

  DOI：10.1021/jf506135c

  日期：2015.2.11

  Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,?-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structureactivity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.