(+)-(S)-3-巯基己烷-1-醇 | 90180-90-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: (+)-(S)-3-巯基己烷-1-醇
• 英文名称: (+)-(S)-3-mercaptohexan-1-ol
• 英文别名: 3-Mercaptohexanol, (S)-；(3S)-3-sulfanylhexan-1-ol
• CAS: 90180-90-8
• 化学式: C₆H₁₄OS
• 分子量: 134.243
• InChiKey: TYZFMFVWHZKYSE-LURJTMIESA-N

物化性质

• 沸点：
  212.4±23.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)
• LogP：
  1.640 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-3-巯基己烷-1-醇 反应 96.0h， 生成 Acetic acid (S)-3-((S)-2-phenyl-propionylsulfanyl)-hexyl ester
  参考文献：
  名称：

  手性，schwefelhaltige香气和百香果（西番莲），对映体和绝对构象

  摘要：

  将黄色百香果的3-甲基硫代己烷-1-醇和2-甲基-4-丙基-1,3-氧杂蒽，手性含S的香气物质拆分为对映异构体，并阐明了其绝对构型。

  DOI：

  10.1016/s0040-4039(00)99923-4
• 作为产物：
  描述：

  2,2-dimethyl-propionic acid 3-formyloxy-hexyl ester 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (+)-(S)-3-巯基己烷-1-醇
  参考文献：
  名称：

  Stereoisomeric Distribution of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate in Dry and Sweet White Wines Made from Vitis vinifera (Var. Sauvignon Blanc and Semillon)

  摘要：

  The enantiomeric distribution of 3-mercaptohexan-1-ol (3MH) and 3-mercaptohexyl acetate (3MHA) in Vitis vinifera wines was determined by combining two techniques: specific purification of volatile thiols from the wines using p-hydroxymercuribenzoate and separation of the chiral molecules by gas-phase chromatography on a cyclodextrin capillary column. The R and S enantiomer ratios of these two thiols in dry white Sauvignon blanc and Semillon wines are approximately 30: 70 for A3MH and 50: 50 for 3MH. However, in sweet white wines made from grapes affected by "noble rot" due to the development of Botrytis cinerea on ripe grapes, the proportion of the R and S forms of 3MH is in the vicinity of 30:70. During alcoholic fermentation, a change in the ratio of the two enantiomers of 3MH in dry white wines was observed. At the beginning of fermentation (around density 1.08), the S form represented over 60%; then, at lower density, as fermentation proceeded, the enatiomeric ratio approached 50:50. The ratio of the two 3MHA enantiomers remained constant throughout fermentation. On the contrary, the distribution of the two 3MH enantiomers changed very little during fermentation of the botrytized sweet wines. The perception thresholds for the R and S forms of 3MH in hydroalcoholic model solution are similar (50 and 60 ng/L). These two enantiomers have quite different aromas: The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit. The perception thresholds of the R and S enantiomers of 3MHA are slightly different (9 and 2.5 ng/L). The less odoriferous R form is reminiscent of passion fruit, while the S form has a more herbaceous odor of boxwood.

  DOI：

  10.1021/jf061566v

文献信息

• Intramolecular Sulfur Transfer in <i>N</i><i>-</i>Enoyl Oxazolidine-2-thiones Promoted by Brønsted Acids. Practical Asymmetric Synthesis of β-Mercapto Carboxylic Acids and Mechanistic Insights
  作者：Claudio Palomo、Mikel Oiarbide、Rosa López、Pedro B. González、Enrique Gómez-Bengoa、José M. Saá、Anthony Linden

  DOI：10.1021/ja0654027

  日期：2006.11.1

  usually above 95:5. The relative efficiency of a range of acids (trifluoroacetic, difluoroacetic, acetic, triflic) is assessed showing TFA and TfOH as the most efficient and acetic acid as a totally inefficient reaction promoter. The new procedure complements the Lewis acid promoted reaction previously described by our group in two aspects: First, stereodivergent results are obtained for the Lewis acid

  证明了单独使用布朗斯台德酸有效促进 N-烯酰基恶唑烷-2-硫酮中的硫转移过程以产生 β-巯基羰基衍生物的能力。该反应对一系列烷基取代的 N-烯酰基恶唑烷-2-硫酮（dr 通常高于 98:2）进行了基本上完美的非对映控制，并且对大多数芳基取代的对应物（dr 通常高于 92:8）具有高选择性。重要的是，该反应在 β,β-二取代的 N-烯酰基恶唑烷-2-硫酮中也非常有效，产生选择性通常高于 95:5 的四元 CS 立体中心。评估了一系列酸（三氟乙酸、二氟乙酸、乙酸、三氟甲磺酸）的相对效率，显示 TFA 和 TfOH 是最有效的，而乙酸则是完全低效的反应促进剂。新程序在两个方面补充了我们小组先前描述的路易斯酸促进反应：首先，对路易斯酸或布朗斯台德酸促进的β，β-二取代烯酰基化合物的反应获得了立体发散结果。其次，虽然布朗斯台德酸促进的反应是立体有择的，在底物 E/Z 构型和产物立体化学之间提供了良好的相关性，但由路易斯酸
• Stereoselectivity of the Generation of 3-Mercaptohexanal and 3-Mercaptohexanol by Lipase-Catalyzed Hydrolysis of 3-Acetylthioesters
  作者：Hidehiko Wakabayashi、Motoko Wakabayashi、Wolfgang Eisenreich、Karl-Heinz Engel

  DOI：10.1021/jf030166u

  日期：2003.7.1

  significantly in terms of activity and enantioselectivity (E). The highest E value (E = 36) was observed for the hydrolysis of 3-acetylthiohexanal catalyzed by lipase B from Candida antarctica resulting in (S)-configured thiol products. Immobilization of the enzyme (E = 85) and the use of tert-butyl alcohol as cosolvent (E = 49) improved the enantioselectivity. Modification of the acyl moiety of the substrate

  研究了通过相应的3-乙酰基硫酯的脂肪酶催化水解，生成两种强效的含硫芳香化合物3-巯基己醛和3-巯基己醇的对映选择性。动力学解析的立体化学过程是通过毛细管气相色谱法进行的，其中使用修饰的环糊精作为手性固定相。所测试的酶制剂在活性和对映选择性（E）方面差异很大。对于来自南极假丝酵母的脂肪酶B催化的3-乙酰基硫己醛水解，观察到最高的E值（E = 36）。固定化酶（E = 85）和使用叔丁醇作为助溶剂（E = 49）提高了对映选择性。底物的酰基部分（3-苯甲酰基硫己醛）的修饰没有显着影响。所研究的含硫化合物具有诱人的气味性能，只有一种对映异构体表现出令人愉悦的柑橘型香气。
• A New One-Step Strategy for the Stereochemical Assignment of Acyclic 2- and 3-Sulfanyl-1-alkanols Using the CD Exciton Chirality Method
  作者：Bernhard Weckerle、Peter Schreier、Hans-Ulrich Humpf

  DOI：10.1021/jo010768h

  日期：2001.11.1

  A new one-step strategy is described for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method. Using the 9-anthroate chromophore for the derivatization of both functional groups, the resulting bisignate CD curves unequivocally allow the determination of the stereochemistry from a single CD measurement. The usefulness of the new method is demonstrated

  使用CD激子手性方法描述了一种新的一步策略，用于无环2和3硫烷基-1-烷醇的立体化学分配。使用9-邻苯二甲酸盐生色团将两个官能团衍生化，生成的双符号CD曲线明确地允许从单个CD测量值确定立体化学。使用合成的光学纯的3-硫烷基-1-己醇和2-硫烷基-1-己醇作为模型化合物证明了该新方法的有效性。发达的微型方法也可用于1,2-和1,3-二醇的立体化学分配。据我们所知，这是CD激子手性方法在无环2-和3-硫烷基-1-链烷醇上的首次应用。
• Enantioselective synthesis of (+)- and (−)-<i>cis</i>-2-methyl-4-propyl-1,3-oxathiane and their olfactive properties
  作者：Wihelm Pickenhagen、Helene Brönner-Schindler

  DOI：10.1002/hlca.19840670405

  日期：1984.6.20

  The enantioselective synthesis of (+)- and (−)-cis-2-methyl-4-propyl-1,3-oxathine 8 and 9 form (E)-2-hezen-1-ol (1) as common starting material is described. The two enantiomeric forms exhibit different organoleptic properties.

  （+）-和（-）-顺式-2-甲基-4-丙基-1,3-草嘌呤8和9的对映选择性合成形式为（E）-2-hezen-1-ol（1）作为常见起始原料描述。两种对映体形式表现出不同的感官特性。
• Reactivity of wine polyphenols under oxidation conditions: Hemisynthesis of adducts between grape catechins or oak ellagitannins and odoriferous thiols
  作者：Emilie Petit、Rémi Jacquet、Laurent Pouységu、Denis Deffieux、Stéphane Quideau

  DOI：10.1016/j.tet.2018.11.071

  日期：2019.2

  solutions to dehydrogenate grape (epi)catechins and oak ellagitannins in the presence of two typical odoriferous thiols, 2-furanmethanethiol (2FMT) and 3-sulfanylhexan-1-ol (3SH). The preparative-scale conditions used enabled the isolation of six novel 2FMT-bearing (epi)catechin derivatives, three known 3SH-bearing catechin derivatives (the structures of two of those were revised to be strictly derived from

  为特征的有气味硫醇的葡萄酒在橡木制成的桶和在瓶子随后的存储的老化过程中损失的原因已经在部分归因于这些硫醇由多酚酒组件脱氢成电子的共价捕获邻时葡萄酒氧合-quinones 。此处，FeCl 3在两种典型的有味硫醇，2-呋喃甲硫醇（2FMT）和3-硫烷基己基-1-醇（3SH）的存在下，在缺氧的水溶液中使用氧化剂作为氧化剂对葡萄（epi）儿茶素和橡木鞣花单宁进行脱氢。使用的制备规模条件可分离出6种新颖的带有2FMT的（epi）儿茶素衍生物，三种已知的带有3SH的儿茶素衍生物（其中两个的结构经过严格修改，严格由1,6-缀合物的添加衍生而来）三种新颖的带有2FMT的卡斯塔拉金衍生物，以及一种新颖的带有3SH的卡斯塔拉金衍生物。这些基于Castalagin的硫代加合物的结构表明，Castalagin的不同脱氢邻苯三酚环对硫醇的捕获始于IV环，然后是III环，最后是V环。