(E)-1-(Benzylthio)-3,3-dimethylbut-1-ene | 75924-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(Benzylthio)-3,3-dimethylbut-1-ene
• 英文别名: benzyl(3,3-dimethylbut-1-enyl)sulfane；[(E)-3,3-dimethylbut-1-enyl]sulfanylmethylbenzene
• CAS: 75924-72-0
• 化学式: C₁₃H₁₈S
• 分子量: 206.352
• InChiKey: IVOOLRDDKHZPEH-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 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)-3,3-二甲基-1-丁烯基]氯化汞 、 苄硫醇 在 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 5.0h， 以64%的产率得到(E)-1-(Benzylthio)-3,3-dimethylbut-1-ene
  参考文献：
  名称：

  Substitution reactions of vinylmercurials by a free-radical chain mechanism

  摘要：

  DOI：

  10.1021/ja00545a054

文献信息

• Decarbonylation of Salicylaldehyde Activated by<i>p</i>-Cymene Ruthenium(II) Dimer: Implication for Catalytic Alkyne Hydrothiolation
  作者：Sarangapani Modem、Shravankumar Kankala、Ramesh Balaboina、Narasimha Swamy Thirukovela、Sreekantha B. Jonnalagadda、Ravinder Vadde、Chandra Sekhar Vasam

  DOI：10.1002/ejoc.201600809

  日期：2016.9

  A stoichiometric C–H activation/decarbonylation of salicylaldehyde by [(η6-p-cymene)RuCl2]2 gave a carbonyl derivative [(η6-p-cymene)RuCl(CO)(Ph-O)] (1) without the use of CO gas. A variety of polar phosphines were then incorporated into compound 1 to give new RuII cationic catalysts, [(η6-p-cymene)Ru(CO)(Ph-O)L]BF4 (2–8). These were used to catalyse the hydrothiolation of alkynes with a range of thiols

  [(η6-p-cymene)RuCl2]2 化学计量的 C-H 活化/脱羰水杨醛得到羰基衍生物 [(η6-p-cymene)RuCl(CO)(Ph-O)] (1)，但不使用一氧化碳气体。然后将各种极性膦掺入化合物 1 中以得到新的 RuII 阳离子催化剂，[(η6-p-伞花烃)Ru(CO)(Ph-O)L]BF4 (2-8)。它们用于在四氢呋喃水溶液中催化炔烃与一系列硫醇的氢硫醇化反应，以高产率得到抗马尔科夫尼科夫 E-线性乙烯基硫化物。
• Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00089a030

  日期：1994.5

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.
• Benati Luisa, Capella Laura, Montevecchi Pier Carlo, Spagnolo Piero, J. Org. Chem, 59 (1994) N 10, S 2818-2823
  作者：Benati Luisa, Capella Laura, Montevecchi Pier Carlo, Spagnolo Piero

  DOI：——

  日期：——
• Substitution reactions of vinylmercurials by a free-radical chain mechanism
  作者：Glen A. Russell、James Hershberger

  DOI：10.1021/ja00545a054

  日期：1980.12