2-戊硫醇 | 2084-19-7

• 物质功能分类: 香精与香料 - 合成香料 - 硫醇类香料
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: 2-戊硫醇
• 中文别名: 2-巯基戊烷；2-巯基戊烷(2-戊基硫醇)；1-甲基丁硫醇；仲戊硫醇
• 英文名称: pentane-2-thiol
• 英文别名: 2-pentanethiol；Pentanthiol-(2)
• CAS: 2084-19-7
• 化学式: C₅H₁₂S
• mdl: MFCD00053516
• 分子量: 104.216
• InChiKey: QUSTYFNPKBDELJ-UHFFFAOYSA-N

物化性质

• 熔点：
  -168.95°C
• 沸点：
  101 °C(lit.)
• 密度：
  0.827 g/mL at 25 °C(lit.)
• 闪点：
  80 °F
• LogP：
  2.66
• 物理描述：
  colourless liquid
• 溶解度：
  slightly soluble in water; soluble in alcohol
• 折光率：
  1.442-1.452
• 保留指数：
  751

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  3.1
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R10
• WGK Germany：
  3
• 危险品运输编号：
  UN 1993
• 海关编码：
  2930909090
• 包装等级：
  II
• 危险类别：
  3.1

制备方法与用途

毒性

GRAS(FEMA)。

使用限量

FEMA(mg/kg)：焙烤制品 0.06～0.1；冷饮、代乳品 0.02～0.06；肉制品、果汁、果酱、果冻、调味汁、速溶咖啡和茶 0.005～0.05；软糖 0.05～0.1；布丁、明胶冻、小吃食品、甜沙司 0.01～0.05；汤品、乳制品、干酪 0.001～0.01；无醇饮料、水果冰品 0.02～0.04；含醇饮料 0.01～0.03；早餐谷物 0.02～0.05；油脂 0.005～0.02；调味品、糖食、糖霜 0.02～0.1；硬糖 0.03～0.1；胶姆糖 0.01～0.1。

反应信息

• 作为反应物：
  描述：

  2-戊硫醇 在 硝酸 作用下， 生成 2-戊烷磺酸
  参考文献：
  名称：

  Wagner; Reid, Journal of the American Chemical Society, 1931, vol. 53, p. 3410

  摘要：

  DOI：
• 作为产物：
  描述：

  2-戊醇 在 吡啶 、 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-戊硫醇
  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

• Activation and synthetic applications of thiostannanes. Efficient conversion of thiols into disulfides
  作者：Sato Tsuneo、Otera Junzo、Nozaki Hitosi

  DOI：10.1016/s0040-4039(00)94450-2

  日期：1990.1

  Various kinds of thiols are converted into the corresponding disulfides under mild conditions with the aid of alkoxystannane-ferric chloride,

  借助烷氧基锡烷-氯化铁在温和条件下将各种硫醇转化为相应的二硫化物，
• Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage
  作者：Qingle Zeng、Jie Feng、Qiaoling Zhang、Fuhai Li、Lu Yang、Ratnakar Reddy Kuchukulla

  DOI：10.1055/s-0040-1707319

  日期：2021.1

  transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

  已经开发出一种无过渡金属的 t-BuOK 介导的芳基乙烯基硫化物与二芳基氧化膦通过 C-S 键断裂的还原 C-P 交叉偶联反应。该协议不仅允许合成二芳基（2-芳基乙基）氧化膦，而且还通过 C-S 键断裂和一锅 C-C 双键的还原实现了前所未有的 C-P 键构建。
• Chiral Thiols:  The Assignment of Their Absolute Configuration by ¹H NMR
  作者：Silvia Porto、José Manuel Seco、Aurelio Ortiz、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/ol7022196

  日期：2007.11.1

  A general NMR spectroscopy protocol for determination of absolute configuration of thiols, that includes the introduction of new aryl-tert-butoxyacetic acids as chiral derivatizing agents (CDAs), is described.

  描述了用于确定硫醇的绝对构型的通用NMR光谱协议，包括引入新的芳基-叔丁氧基乙酸作为手性衍生剂（CDA）。
• Carbon−Sulfur Bond Cleavage of Methyl-Substituted Thiophenes with Iridium(III)
  作者：Matthew R. Grochowski、William W. Brennessel、William D. Jones

  DOI：10.1021/om900114m

  日期：2009.5.11

  Reaction of [Cp*IrHCl]2 (Cp* = η5-C5Me5) with 2-methylthiophene and 2,5-dimethylthiophene at 120 °C in the presence of H2 results in the cleavage of the thiophene carbon−sulfur bond(s). In both cases the thiophenes are ring-opened and hydrogenated, resulting in dinuclear Ir complexes with bridging thiolates. The primary product in the reaction involving 2,5-dimethylthiophene is [Cp*IrCl]2(μ-H)(μ-S-2-hexyl)

  的[CP * IrHCl]的反应2（CP * =η 5 -C 5我5）与在H 2存在下甲基噻吩和2,5-二甲基噻在120℃ 2个在噻吩碳-硫裂解结果债券。在这两种情况下，噻吩都被开环和氢化，从而生成具有桥连硫醇盐的双核Ir配合物。涉及2,5-二甲基噻吩的反应中的主要产物是[CP * IrCl] 2（μ-H）（μ-S-2-己基）。该产品已经过鉴定，并以非对映异构体形式存在。在与2-甲基噻吩的反应中，产生了由五种产物组成的复杂混合物。产物分布由单取代和双取代的硫醇盐配合物组成，其中三种通过单晶X射线衍射进行了结构表征。这些产物均已独立合成，反应混合物的表征已通过1 H和13 C NMR光谱以及ESI-MS和元素分析完成。与2-乙酰基噻吩的反应显示出非常相似的反应性。X射线结构证实了存在的非对映异构体对的性质。
• 4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas
  作者：Ali Reza Sardarian、Iman Dindarloo Inaloo

  DOI：10.1039/c5ra14528g

  日期：——

  A simple and efficient solvent-free preparation of primary carbamates,S-thiocarbamates and ureas from alcohols, phenols, thiols and amines in the presence of 4-dodecylbenzenesulfonic acid, as a cheap and green Brønsted acid, has been described.

  一种简单高效的无溶剂制备方法，可将醇、酚、硫醇和胺转化为一次氨基甲酸酯、S-硫代氨基甲酸酯和脲，该方法使用4-十二烷基苯磺酸作为廉价环保的Brønsted酸。

表征谱图