3-(thioacetyl)octane | 79355-13-8

• 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: 3-(thioacetyl)octane
• 英文别名: 3-octanethiol thiolacetate；3-Octanethiol, thiolacetate；S-octan-3-yl ethanethioate
• CAS: 79355-13-8
• 化学式: C₁₀H₂₀OS
• 分子量: 188.334
• InChiKey: CDXPXZLNMUTOBE-UHFFFAOYSA-N

物化性质

• 沸点：
  242.7±9.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(thioacetyl)octane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 octane-3-thiol
  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
• 作为产物：
  描述：

  3-辛酮 在 ammonium hydroxide 、 sodium tetrahydroborate 、 三溴化磷 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-(thioacetyl)octane
  参考文献：
  名称：

  合成和评估一些稳定的多底物加合物作为亚精胺合酶的特异性抑制剂。

  摘要：

  设计了一系列新的氨基丙基转移酶抑制剂，其中亲核氨基丙基受体与氨基丙基供体S-腺苷-1-（甲硫基）-3-丙胺（脱羧的S-腺苷甲硫氨酸）连接，形成“多底物加合物”。在当前情况下，已经合成了S-腺苷-1，8-二氨基-3-硫辛烷（2b）和相应的甲基thy盐（3b）。分析了几种这类化合物作为亚精胺合酶的抑制剂，发现2b和3b均为该酶的有效抑制剂。硫醚2b是迄今为止描述的最有效的亚精胺合酶抑制剂，几乎完全没有针对紧密相关的氨丙基转移酶精胺合酶的抑制活性。

  DOI：

  10.1021/jm00143a003

文献信息

• COWARD, J. K.;TANG, KUO-CHANG
  作者：COWARD, J. K.、TANG, KUO-CHANG

  DOI：——

  日期：——
• 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.
• Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase
  作者：Kuo-Chang Tang、Roy Mariuzza、James K. Coward

  DOI：10.1021/jm00143a003

  日期：1981.11

  were assayed as inhibitors of spermidine synthase, and both 2b and 3b were found to be potent inhibitors of the enzyme. The thioether 2b is the most potent inhibitor of spermidine synthase described to date and is almost totally devoid of inhibitory activity against the closely related aminopropyltransferase, spermine synthase. This type of compound should have use as a specific inhibitor of spermidine

  设计了一系列新的氨基丙基转移酶抑制剂，其中亲核氨基丙基受体与氨基丙基供体S-腺苷-1-（甲硫基）-3-丙胺（脱羧的S-腺苷甲硫氨酸）连接，形成“多底物加合物”。在当前情况下，已经合成了S-腺苷-1，8-二氨基-3-硫辛烷（2b）和相应的甲基thy盐（3b）。分析了几种这类化合物作为亚精胺合酶的抑制剂，发现2b和3b均为该酶的有效抑制剂。硫醚2b是迄今为止描述的最有效的亚精胺合酶抑制剂，几乎完全没有针对紧密相关的氨丙基转移酶精胺合酶的抑制活性。