(Z)1-hexenyl p-tolyl sulfide | 127894-29-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)1-hexenyl p-tolyl sulfide
• 英文别名: (Z)-1-(4-methylphenylthio)-1-hexene；(Z)-1-(p-tolylsulfenyl)-1-hexene；(Z)-1-(4-methylphenyl)sulfanyl-1-hexene；(Z)-hex-1-en-1-yl(p-tolyl)sulfane；1-[(Z)-hex-1-enyl]sulfanyl-4-methylbenzene
• CAS: 127894-29-5
• 化学式: C₁₃H₁₈S
• 分子量: 206.352
• InChiKey: DESBDAMOHMDAJP-WDZFZDKYSA-N

物化性质

• 沸点：
  299.3±23.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-(4-methylphenyl)sulfanyl-1-tributylstannyl-1-hexene 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以90%的产率得到(Z)1-hexenyl p-tolyl sulfide
  参考文献：
  名称：

  通过（E）-α-甲锡基乙烯基硫化物的锡-锂交换立体选择性合成（2Z）-2-芳基硫烷基烯丙醇

  摘要：

  (E)-α-甲锡基乙烯基硫化物 1 与正丁基锂的锡-锂交换反应得到 (Z)-α-芳基硫基乙烯基锂 2，其与醛或酮 3 反应得到良好的立体选择性 (2Z)-2-芳基硫基烯丙醇 4到高产。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:639–643, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20487

  DOI：

  10.1002/hc.20487

文献信息

• Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
  作者：Ya-mei Lin、Guo-ping Lu、Gui-xiang Wang、Wen-bin Yi

  DOI：10.1021/acs.joc.6b02459

  日期：2017.1.6

  can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents

  引入了一种新开发的含有酸和磷的水性体系，在该体系中，无味且稳定的芳基亚磺酸钠可以原位生成芳基亚硫基。这些自由基具有与炔烃，烯烃和H-膦氧化物反应的高反应性，以合成烷基硫化物和烯基硫化物以及硫代磷酸硫代酸酯。还进行了控制实验和量子计算，以深入了解芳基亚硫基自由基的生成机理。值得注意的是，该化学物质不含硫醇气味，有机溶剂和金属。
• The Hydroboration of 1-Alkylthio-l-alkynes, and Its Application to the Syntheses of<i>S</i>-Alkyl Alkanethioates and (<i>Z</i>)-1-Alkylthio-1-alkenes
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1246/bcsj.63.447

  日期：1990.2

  Hydroboration of 1-alkylthio-1-alkynes with dicyclohexylborane or bis(1,2-dimethylpropyl)borane proceeded smoothly, adding most of the dialkylboryl group to the α-position of the triple bond. The resulting alkenylboranes afforded either S-alkyl alkanethioates on a controlled oxidation with alkaline hydrogen peroxide in the presence of N,N,N′,N′-etramethylethylenediamine or (Z)-1-alkylthio-1-alkenes on a basic protonolysis, successive treatments with methyllithium, copper(I) iodide and water in the presence of hexamethylphosphoric triamide.

  1-烷基硫-1-炔与二环己基硼或双(1,2-二甲基丙基)硼的水硼化反应顺利进行，将大部分二烷基硼基团添加到三键的α位。所得到的烯基硼烃在控制氧化条件下与碱性过氧化氢反应，可生成S-烷基烷硫酸酯，或在碱性质子解离、与甲基锂、铜(I)碘化物和水依次处理的条件下，生成(Z)-1-烷基硫-1-烯。
• Sulfur-Directed Synthesis of Enantiopure Hydroxy 2-Sulfinyl Butadienes
  作者：Roberto Fernández de la Pradilla、María Victoria Buergo、María Victoria Martínez、Carlos Montero、Mariola Tortosa、Alma Viso

  DOI：10.1021/jo035750g

  日期：2004.3.1

  The treatment of sulfinyl chlorohydrins with KO-t-Bu in THF generates epoxy vinyl sulfoxides that undergo an efficient base-induced rearrangement to generate enantiopure hydroxy 2-sulfinyl dienes. This novel process takes place with high chemo- and stereoselectivity. The chirality at sulfur effectively controls the geometry of the trisubstituted alkene.

  在THF中用KO- t- Bu处理亚磺酰氯醇会生成环氧乙烯基亚砜，这些环氧亚砜会进行有效的碱诱导的重排，从而生成对映纯的羟基2-亚磺酰基二烯。这种新颖的过程具有很高的化学选择性和立体选择性。硫的手性有效地控制了三取代烯烃的几何形状。
• Nucleophilic Epoxidation of α‘-Hydroxy Vinyl Sulfoxides
  作者：Roberto Fernández de la Pradilla、Jorge Fernández、Pilar Manzano、Paloma Méndez、Julián Priego、Mariola Tortosa、Alma Viso、Martín Martínez-Ripoll、Ana Rodríguez

  DOI：10.1021/jo026182s

  日期：2002.11.1

  The nucleophilic epoxidation of a variety of alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.
• HOSHI, MASAYUKI;MASUDA, YUZURU;ARASE, AKIRA, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 447-452
  作者：HOSHI, MASAYUKI、MASUDA, YUZURU、ARASE, AKIRA

  DOI：——

  日期：——