2-巯基-3-甲基-1-丁醇 | 116229-37-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: 2-巯基-3-甲基-1-丁醇
• 中文别名: 2-疏基-3-甲基-1-丁醇
• 英文名称: rac-3-methyl-2-mercapto-1-butanol
• 英文别名: 2-mercapto-3-methyl-1-butanol；2-mercapto-3-methylbutanol；3-Methyl-2-sulfanylbutan-1-ol
• CAS: 116229-37-9
• 化学式: C₅H₁₂OS
• 分子量: 120.216
• InChiKey: QBYYSQQYPUMFOX-UHFFFAOYSA-N

物化性质

• 沸点：
  178.0±23.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)
• 保留指数：
  964

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 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：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-巯基-3-甲基-1-丁醇 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.0h， 生成 methyl E-(5RS)-2-cyanomethylene-5-hydroxymethyl-6-methyl-4-thia-heptanoate
  参考文献：
  名称：

  Effects of configuration and N-substitution on the formation of ß-lactams from bicyclic cyano-substituted isoxazolidines

  摘要：

  The 4-cyano-substituted bicyclic compounds 10 and 11 were prepared by reaction of the aldehyde dimer 7 with a cis-trans mixture of 4-bromo crotononitrile followed by treatment with corresponding N-substituted hydroxyamines. The diastereomers 10a and 10b could be separated by flash chromatography. The key step in the synthesis of compounds 15 and 16 was the Wittig reaction of 13 with cyanomethylene tripheriylphosphorane affording a mixture of diastereomers 14a and 14b, which were separated by flash chromatography. Separate Swern oxidation of 14a and 14b, followed by reaction with N-(4-tert-butylphenyl)hydroxylamine gave bicyclic compounds 15a and 15b, respectively. In the same way 16b was prepared.The action of lithium diisopropylamide on the N-aryl-substituted compounds 10b and 15b possessing an exo-hydrogen atom at 4-position converted these to the bicyclic B-lactams 18 and 19, respectively. In contrast neither diastereomers 10a and 15a with an endo-hydrogen atom, nor the N-alkyl-substituted compounds 11 or 16b, nor compounds of type 17 were affected by LDA under equal conditions.

  DOI：

  10.1016/s0040-4020(01)89669-1
• 作为产物：
  描述：

  2-溴代异戊酸 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 四氯化钛 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 75.0h， 生成 2-巯基-3-甲基-1-丁醇
  参考文献：
  名称：

  Preparation of vic-Mercaptoisopentanols

  摘要：

  这篇论文描述了一些巯基异戊醇的制备过程：2-巯基-3-甲基-1-丁醇（I）、1-巯基-3-甲基-2-丁醇（II）、3-巯基-3-甲基-2-丁醇（III）以及化合物I的不饱和类似物-2-巯基-3-甲基-2-丁烯-1-醇（IV）。这些化合物属于食物中存在的类黄酮类化合物，会导致食物味道恶化。

  DOI：

  10.1135/cccc19930404

文献信息

• Wu, Shao-Yong; Hirashima, Akinori; Takeya, Ryuko, Agricultural and Biological Chemistry, 1988, vol. 52, # 11, p. 2911 - 2918
  作者：Wu, Shao-Yong、Hirashima, Akinori、Takeya, Ryuko、Eto, Morifusa

  DOI：——

  日期：——
• WU, SHAO-YONG;HIRASHIMA, AKINORI;TAKEYA, RYUKO;ETO, MORIFUSA, ARG. AND BIOL. CHEM., 52,(1988) N1, C. 2911-2917
  作者：WU, SHAO-YONG、HIRASHIMA, AKINORI、TAKEYA, RYUKO、ETO, MORIFUSA

  DOI：——

  日期：——
• Preparation of vic-Mercaptoisopentanols
  作者：Daniel Végh、Michal Uher、Oľga Rajniaková、Miloslava Dandárová、Milan Kováč

  DOI：10.1135/cccc19930404

  日期：——

  This paper describes the preparation of some mercaptoisopentanols: 2-mercapto-3-methyl-1-butanol (I), 1-mercapto-3-methyl-2-butanol (II), 3-mercapto-3-methyl-2-butanol (III) and the unsaturated analogue of compound I - 2-mercapto-3-methyl-2-buten-1-ol (IV). These compounds belong to the flavonoid group present in food responsible for deterioration of their gustatory properties.

  这篇论文描述了一些巯基异戊醇的制备过程：2-巯基-3-甲基-1-丁醇（I）、1-巯基-3-甲基-2-丁醇（II）、3-巯基-3-甲基-2-丁醇（III）以及化合物I的不饱和类似物-2-巯基-3-甲基-2-丁烯-1-醇（IV）。这些化合物属于食物中存在的类黄酮类化合物，会导致食物味道恶化。
• Effects of configuration and N-substitution on the formation of ß-lactams from bicyclic cyano-substituted isoxazolidines
  作者：Hans Günter Aurich、Jose-Luis Ruiz Quintero

  DOI：10.1016/s0040-4020(01)89669-1

  日期：1994.3

  The 4-cyano-substituted bicyclic compounds 10 and 11 were prepared by reaction of the aldehyde dimer 7 with a cis-trans mixture of 4-bromo crotononitrile followed by treatment with corresponding N-substituted hydroxyamines. The diastereomers 10a and 10b could be separated by flash chromatography. The key step in the synthesis of compounds 15 and 16 was the Wittig reaction of 13 with cyanomethylene tripheriylphosphorane affording a mixture of diastereomers 14a and 14b, which were separated by flash chromatography. Separate Swern oxidation of 14a and 14b, followed by reaction with N-(4-tert-butylphenyl)hydroxylamine gave bicyclic compounds 15a and 15b, respectively. In the same way 16b was prepared.The action of lithium diisopropylamide on the N-aryl-substituted compounds 10b and 15b possessing an exo-hydrogen atom at 4-position converted these to the bicyclic B-lactams 18 and 19, respectively. In contrast neither diastereomers 10a and 15a with an endo-hydrogen atom, nor the N-alkyl-substituted compounds 11 or 16b, nor compounds of type 17 were affected by LDA under equal conditions.