3-mercaptopentan-1-ol | 548740-99-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 3-mercaptopentan-1-ol
• 英文别名: 3-sulfanylpentan-1-ol；3-mercaptopentanol
• CAS: 548740-99-4
• 化学式: C₅H₁₂OS
• 分子量: 120.216
• InChiKey: PRJACVDGNSZBLE-UHFFFAOYSA-N

物化性质

• 溶解度：
  氯仿（微溶）、二氯甲烷（微溶）、甲醇（微溶）
• 保留指数：
  1002;1002;1002;1009

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  3
• 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

安全信息

• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P210,P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
• 危险品运输编号：
  1760
• 危险性描述：
  H302,H315,H318,H335,H227

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 3-mercaptopentan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid 3-benzoylsulfanyl-pentyl ester
  参考文献：
  名称：

  通过路易斯酸促进的N-烯酰基恶唑烷-2-硫酮中的分子内硫转移，不对称合成β-巯基羧酸衍生物。

  摘要：

  DOI：

  10.1021/ja015860+
• 作为产物：
  描述：

  thioacetic acid S-(1-ethyl-3-oxopropyl) ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到3-mercaptopentan-1-ol
  参考文献：
  名称：

  Odorous Impact of Volatile Thiols on the Aroma of Young Botrytized Sweet Wines:  Identification and Quantification of New Sulfanyl Alcohols

  摘要：

  Specific extraction of volatile thiols using sodium p-hydroxymercuribenzoate revealed the presence of three new sulfanylalcohols in wines made from Botrytis-infected grapes: 3-sulfanylpentan-1-ol (II), 3-sulfanylheptan-1-ol (III), and 2-methyl-3-sulfanylbutan-1-ol (IV). The first two have citrus aromas, whereas the third is reminiscent of raw onion. In addition, 2-methyl-3-sulfanylpentan-1-ol, which has a raw onion odor, was tentatively identified. Like 3-sulfanylhexan-1-ol (I), already reported in Sauternes wines, compounds II, III, and IV were absent from must. They were found in wine after alcoholic fermentation, and their concentrations were drastically higher when Botrytis cinerea had developed on the grapes. In the commercial botrytized wines analyzed, the mean levels of II, III, and IV were 209, 51, and 103 ng/L, respectively. Despite their low odor activity values, sensory tests showed additive effects among I, II, and III, thus confirming their olfactory impact on the overall aroma of botrytized wines.

  DOI：

  10.1021/jf062582v

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
• Identification of Odoriferous Sulfanylalkanols in Human Axilla Secretions and Their Formation through Cleavage of Cysteine Precursors by a CS Lyase Isolated from Axilla bacteria
  作者：Andreas Natsch、Joachim Schmid、Felix Flachsmann

  DOI：10.1002/cbdv.200490079

  日期：2004.7

  was postulated that the odorless precursors for these compounds are cysteine conjugates. Bacterial isolates obtained from the human axilla and belonging to the Corynebacteria were, indeed, found to have the enzymatic capacity to release various thiols from cysteine conjugates. The metC gene, which is known to code for a cystathione-beta-lyase, was cloned from the axilla isolate Corynebacterium striatum

  已知在棒状杆菌属菌的作用下会形成人腋臭。本身无味的腋窝分泌物。除了已知的臭味酸，我们报告了在人腋窝分泌物中出现了四种臭味的硫烷基链烷醇，即3-硫烷基己基-1-醇（3），2-甲基-3-硫烷基丁烷-1-醇（4），3-硫基戊基戊烷- 1-醇（5）和3-甲基-3-硫烷基己基-1-醇（6）。这些化合物具有刺鼻的汗水/厨房气味，还让人联想到带有水果味的洋葱，其感知阈值在pg / l范围内。假定这些化合物的无味前体是半胱氨酸缀合物。实际上，发现从人腋下获得的属于棒状杆菌的细菌分离物具有从半胱氨酸缀合物释放各种硫醇的酶促能力。metC基因，从腋窝分离株纹状体棒状杆菌Ax20中克隆了已知编码胱硫醚-β-裂合酶的蛋白，并在大肠杆菌中异源表达。纯重组酶可裂解各种半胱氨酸结合物，并具有与野生型细胞匀浆相似的底物特异性。最后，将重组酶与无味的腋窝分泌物一起孵育，并释放出有味的硫醇。
• TURYANSKAYA, A. M.;GREN, A. I.;BACHERIKOV, V. A., VINITI 792-85
  作者：TURYANSKAYA, A. M.、GREN, A. I.、BACHERIKOV, V. A.

  DOI：——

  日期：——
• Asymmetric Synthesis of β-Mercapto Carboxylic Acid Derivatives by Intramolecular Sulfur Transfer in <i>N</i>-Enoyl Oxazolidine-2-thiones Promoted by Lewis Acids
  作者：Claudio Palomo、Mikel Oiarbide、Flavia Dias、Aurelio Ortiz、Anthony Linden

  DOI：10.1021/ja015860+

  日期：2001.6.1
• Odorous Impact of Volatile Thiols on the Aroma of Young Botrytized Sweet Wines:  Identification and Quantification of New Sulfanyl Alcohols
  作者：Elise Sarrazin、Svitlana Shinkaruk、Takatoshi Tominaga、Bernard Bennetau、Eric Frérot、Denis Dubourdieu

  DOI：10.1021/jf062582v

  日期：2007.2.1

  Specific extraction of volatile thiols using sodium p-hydroxymercuribenzoate revealed the presence of three new sulfanylalcohols in wines made from Botrytis-infected grapes: 3-sulfanylpentan-1-ol (II), 3-sulfanylheptan-1-ol (III), and 2-methyl-3-sulfanylbutan-1-ol (IV). The first two have citrus aromas, whereas the third is reminiscent of raw onion. In addition, 2-methyl-3-sulfanylpentan-1-ol, which has a raw onion odor, was tentatively identified. Like 3-sulfanylhexan-1-ol (I), already reported in Sauternes wines, compounds II, III, and IV were absent from must. They were found in wine after alcoholic fermentation, and their concentrations were drastically higher when Botrytis cinerea had developed on the grapes. In the commercial botrytized wines analyzed, the mean levels of II, III, and IV were 209, 51, and 103 ng/L, respectively. Despite their low odor activity values, sensory tests showed additive effects among I, II, and III, thus confirming their olfactory impact on the overall aroma of botrytized wines.