丁基1-环己烯基硫醚 | 57297-59-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 丁基1-环己烯基硫醚
• 英文名称: butyl 1-cyclohexenyl sulfide
• 英文别名: 1-(butylthio)-1-cyclohexene；1-Butylthio-1-cyclohexene；1-(butylthio)cyclohexene；1-n-butylthiocyclohexene；1-Butylmercapto-cyclohexen-(1)；1-n-Butylthio-1-cyclohexen；Dhwyccuuwkegof-uhfffaoysa-；1-butylsulfanylcyclohexene
• CAS: 57297-59-3
• 化学式: C₁₀H₁₈S
• 分子量: 170.319
• InChiKey: DHWYCCUUWKEGOF-UHFFFAOYSA-N

物化性质

• 沸点：
  95 °C(Press: 2.5 Torr)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丁基1-环己烯基硫醚 在 水 、 lithium carbonate 、 mercury dichloride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(2-氧代-2-苯乙基)-环己酮
  参考文献：
  名称：

  Three-component radical condensations involving benzoylmethyl radicals, alkenes, and diphenyl disulfide

  摘要：

  Acyl-substituted methyl radicals (RCOCH2.; R = H, Me, Ph), generated by photolysis of RCOCH2-HgCl, add to alkenes, enol ethers, or vinyl sulfides to give adduct radicals that are readily trapped by PhSSPh to yield a three-component condensation product. The presence of an alkali metal carbonate is crucial in preventing side reactions resulting in the conversion of the mercurial to RCOCH3 by PhSH formed in the photolysis.

  DOI：

  10.1021/jo00062a008
• 作为产物：
  描述：

  1,1-Bis(n-butylthio)-cyclohexan 以 氯苯 为溶剂， 生成 丁基1-环己烯基硫醚
  参考文献：
  名称：

  Free radical rearrangement of cyclic ketone mercaptols

  摘要：

  DOI：

  10.1007/bf01100019

文献信息

• Functionalized olefin cross-coupling to construct carbon–carbon bonds
  作者：Julian C. Lo、Jinghan Gui、Yuki Yabe、Chung-Mao Pan、Phil S. Baran

  DOI：10.1038/nature14006

  日期：2014.12.18

  Carbon–carbon (C–C) bonds form the backbone of many important molecules, including polymers, dyes and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavour relies heavily on the ability to form C–C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a chemical transformation that allows the facile construction of highly substituted and uniquely functionalized C–C bonds. Using a simple iron catalyst, an inexpensive silane and a benign solvent under ambient atmosphere, heteroatom-substituted olefins are easily reacted with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than 60 examples are presented with a wide array of substrates, demonstrating the chemoselectivity and mildness of this simple reaction. Highly substituted carbon–carbon bonds are constructed using a simple iron catalyst and an inexpensive silane: more than 60 examples of this reaction — in which heteroatom-substituted olefins are reacted with electron-deficient olefins — are presented. This paper reports the development of a new type of carbon–carbon bond forming reaction that allows for the simple construction of molecules that were previously either impossible or laborious to access. The procedure exploits an interaction between heteroatom-substituted olefins and electron-deficient olefins to construct highly substituted carbon–carbon bonds using a simple iron catalyst and an inexpensive silane. The authors present than sixty examples of this reaction, covering a broad range of substrates. This reaction is of relevance to the design of organic compounds including polymers, dyes, and pharmaceutical agents and semiconductors.

  碳-碳（C-C）键构成了许多重要分子（包括聚合物、染料及医药制剂）的骨架。大量有机化学家致力于开发新的方法，以期能快速高效地制备这些重要的C-C键。该研究项目更多地依赖于在某些特殊的官能团及空间位阻的环境下形成C-C键的能力。本文报道了一种化学转变过程，这一进程使得传统方法难以形成的具有高度空间位阻及特殊官能团的C-C键能够简易地构建出来。通过使用简便的铁基催化剂，廉价的硅烷及环保的溶剂，在常温常压条件下，很容易使一些含有杂原子的烯烃与那些缺电子的烯烃反应，进而形成一些以往在技术上很难实现甚至无法实现的分子结构。超过60种底物的实验数据的展示，表明了这一简便反应所具有的选择性及温和性。通过简便的铁基催化剂及廉价的硅烷，高度取代的碳-碳键被构建出来。超过60种例子探究了这种反应——含有杂原子的烯烃与那些缺电子的烯烃的反应。本文报道了一种新型的C-C键形成反应，该反应使得一些过去在技术上无法实现或极难实现的分子结构能够简单地构建出来。这一过程利用了含有杂原子的烯烃与缺电子烯烃的相互作用，通过简便的铁基催化剂及廉价的硅烷构建出高度取代的C-C键。超过60种实验例子，广泛地展示了这一过程的通用性。这一反应与包括聚合物、染料及医药制剂，半导体等领域有机化合物的合成息息相关。
• Clay Catalysis: A Simple and Efficient Synthesis of Enolthioethers from Cyclic Ketones
  作者：Bouchta Labiad、Didier Villemin

  DOI：10.1055/s-1989-27180

  日期：——

  Montmorillonite KSF in refluxing toluene catalyses the synthesis of 1-alkyl- and 1-arylthioalkenes from ketones and thiols (thiophenol or 1-butanethiol).

  蒙脱石 KSF 在回流的甲苯中催化从酮和硫醇（硫基苯或 1-丁硫醇）合成 1-烷基和 1-芳基硫烷烯。
• Cyclobutane derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US05250697A1

  公开（公告）日：1993-10-05

  Cyclobutane derivatives represented by the following general formula (I): ##STR1## wherein X represents a group represented by the formula ##STR2## or the formula ##STR3## which is expected to be useful as reagents, drugs, agricultural chemicals and perfumes as well as an intermediate for the preparation thereof.

  以下是用下列通式（I）表示的环丁烷衍生物：##STR1## 其中X表示公式##STR2##或公式##STR3##表示的基团，预计可用作试剂、药物、农业化学品和香料，以及其制备的中间体。
• Asymmetric [2+2] Cycloaddition Reaction between α,β-Unsaturated Acid Derivatives and Alkynyl or Alkenyl Sulfides Catalyzed by a Chiral Titanium Reagent
  作者：Yujiro Hayashi、Koichi Narasaka

  DOI：10.1246/cl.1990.1295

  日期：1990.8

  Asymmetric [2+2] cycloaddition reaction between 3-(acryloyl)-1,3-oxazolidin-2-one derivatives and alkynyl or alkenyl sulfides proceeds by the use of a chiral titanium reagent to give the corresponding cyclobutene or cyclobutane derivatives in high enantioselectivity.

  3-(丙烯酰基)-1,3-恶唑烷-2-酮衍生物与炔基或烯基硫化物之间的不对称[2+2]环加成反应通过使用手性钛试剂进行，以高对映选择性得到相应的环丁烯或环丁烷衍生物.
• Acylation of Butylthio or Phenylthio Cycloalkenes. Catalysis by Aluminium Exchanged Clay
  作者：Didier Villemin、Bouchta Labiad

  DOI：10.1080/00397919208021131

  日期：1992.12

  Abstract Thiobutyl or thiophenylcycloalkenes were acylated by acetyl or benzoyl chloride in the presence of aluminium trichloride. Aluminium exchanged montmorillonite catalysed the reaction and gave a better yield than with a stoechiometric quantity of aluminium trichloride.

  摘要 在三氯化铝存在下，用乙酰基或苯甲酰氯酰化硫丁基或硫苯基环烯烃。铝交换的蒙脱石催化反应并且比化学计量量的三氯化铝产生更好的产率。