<2-Methyl-hexyl-(3)>-tosylat | 92372-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <2-Methyl-hexyl-(3)>-tosylat
• 英文别名: 2-Methylhexan-3-yl 4-methylbenzenesulfonate
• CAS: 92372-39-9
• 化学式: C₁₄H₂₂O₃S
• 分子量: 270.393
• InChiKey: NKBKESDDKKCLFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2-Methyl-hexyl-(3)>-tosylat 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-methylhexane-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：

  2-甲基-3-己醇 、 4-甲苯磺酸酐 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到<2-Methyl-hexyl-(3)>-tosylat
  参考文献：
  名称：

  高效温和的镱 (III) 催化醇的甲苯磺酰化

  摘要：

  三氟甲磺酸镱 (III) 可有效催化伯醇和仲醇与甲苯磺酸酐的反应，以高收率生成甲苯磺酸烷基酯。反应在中性温和条件下进行，产物纯化很容易通过短柱色谱法实现。

  DOI：

  10.1055/s-2004-815998

文献信息

• SUBSTITUTED PYRAZOLES AS MODULATORS OF CHEMOKINE RECEPTORS
  申请人：Merck & Co., Inc.

  公开号：EP1853260A1

  公开（公告）日：2007-11-14
• [EN] SUBSTITUTED PYRAZOLES AS MODULATORS OF CHEMOKINE RECEPTORS<br/>[FR] PYRAZOLES SUBSTITUES COMME MODULATEURS DES RECEPTEURS DES CHIMIOKINES
  申请人：MERCK & CO INC

  公开号：WO2006088813A1

  公开（公告）日：2006-08-24

  [EN] Substituted pyrazole compounds such compounds represented by formula I: which are used to modulate the CCR-2 chemokine receptor to prevent or treat inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis; and pharmaceutical compositions comprising these compounds and the use of these compounds and compositions.
  [FR] L'invention concerne des composés de pyrazole substitués représentés par la formule I, qui sont utilisés pour moduler le récepteur des chimiokines CCR-2 afin de prévenir ou de traiter des troubles et des maladies inflammatoires et liées à l'immunomodulation, des maladies allergiques, des états atopiques comprenant la rhinite allergique, la dermatite, la conjonctivite et l'asthme, ainsi que des pathologies auto-immunes telles que la polyarthrite rhumatoïde et l'athérosclérose. L'invention concerne aussi des compositions pharmaceutiques comprenant ces composés ainsi que l'utilisation de ces composés et compositions.
• 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.
• <b>Efficient and Mild Ytterbium(III)-Catalyzed Tosylation of Alcohols</b>
  作者：Ralf Schirrmacher、Slobodan Comagic

  DOI：10.1055/s-2004-815998

  日期：——

  Ytterbium(III) trifluoromethanesulfonate efficiently catalyzes the reaction of primary and secondary alcohols with toluenesulfonic acid anhydride to yield the alkyl tosylates in high yields. The reactions were carried outunder neutral and mild conditions and product purification was easily achieved by means of short column chromatography.

  三氟甲磺酸镱 (III) 可有效催化伯醇和仲醇与甲苯磺酸酐的反应，以高收率生成甲苯磺酸烷基酯。反应在中性温和条件下进行，产物纯化很容易通过短柱色谱法实现。

表征谱图