n-butyl 2-tolyl sulfide | 15560-99-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: n-butyl 2-tolyl sulfide
• 英文别名: Sulfide, butyl o-tolyl；1-butylsulfanyl-2-methylbenzene
• CAS: 15560-99-3
• 化学式: C₁₁H₁₆S
• 分子量: 180.314
• InChiKey: RNLYLNHPQLCRFI-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 12 Torr)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  n-butyl 2-tolyl sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以1.3 g的产率得到1-(butylsulfinyl)-2-methylbenzene
  参考文献：
  名称：

  苯胺与烷基（芳基）ulf盐的 Ullmann型N-芳基化反应†

  摘要：

  使用烷基（芳基）ulf三氟甲磺酸酯作为芳基化试剂，实现了钯/铜共催化的苯胺的Ullmann型N-芳基化。该反应通过Pd（P（t Bu）3）2 / CuI使烷基（芳基）s的C烷基-S键断裂，使C芳基-S键断裂，并以高至高收率得到了相应的N-芳基化产物。同样重要的是，苯胺与不对称的丁基（甲磺酰基）（芳基）ulf三氟甲磺酸酯的反应显示出优异的选择性，其中除了庞大的和富电子的甲磺酰基部分以外的芳基都发生了转化。

  DOI：

  10.1039/c9cc06535k
• 作为产物：
  描述：

  邻甲苯磺酰氯 在 盐酸 、 sodium hydroxide 、 铁粉 作用下， 生成 n-butyl 2-tolyl sulfide
  参考文献：
  名称：

  Profft, Chemische Technik, 1953, vol. 5, p. 239,241

  摘要：

  DOI：

文献信息

• C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes
  作者：Fang-Jie Guo、Jing Sun、Zhao-Qing Xu、Fritz E. Kühn、Shu-Liang Zang、Ming-Dong Zhou

  DOI：10.1016/j.catcom.2017.02.007

  日期：2017.6

  C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the

  研究了原位生成的Ni（II）N-杂环卡宾（NHC）配合物催化的芳基卤化物与烷基硫醇的CS交叉偶联。当使用5 mol％的Ni（II）-NHC催化剂和1.5 eq。的Ni（II）-NHC催化剂时，对于各种芳基卤化物，可以获得良好或优异的收率。的KO Ť卜。考察了NHC配体对Ni（II）-NHC催化性能的电子和空间效应，以及芳基卤化物对偶合反应性的电子效应。还讨论了Ni（II）-NHC催化偶联反应的机理。
• <i> <scp>L</scp> </i>‐Proline‐Promoted CuI‐Catalyzed C‐S Bond Formation between Aryl Iodides and Thiols
  作者：Hui Zhang、Weiguo Cao、Dawei Ma

  DOI：10.1080/00397910600977533

  日期：2007.1.1

  Abstract An improved, mild procedure for the CuI‐catalyzed coupling reactions of aryl iodides with aliphatic and aromatic thiols, using L ‐proline as the ligand, is reported. This procedure is noteworthy given its high generality and exceptional level of functional group toleration.

  摘要报道了一种使用 L-脯氨酸作为配体的 CuI 催化的芳基碘化物与脂肪族和芳香族硫醇的偶联反应的改进的温和程序。鉴于其高度的通用性和特殊的官能团耐受水平，该过程值得注意。
• Cu-Catalyzed Coupling of Aryl Iodides with Thiols Using Carbonyl-Phosphine Oxide Ligands
  作者：Haolong WANG、Boshun WAN

  DOI：10.1016/s1872-2067(10)60243-4

  日期：2011.1

  A series of carbonyl-phosphine oxide ligands were synthesized from 2-bromophenylaldehyde and used in Cu-catalyzed C-S coupling reactions. Aryl iodide and aryl bromide reacted with thiols efficiently upon catalysis under mild reaction conditions and a yield of up to 99% was obtained.

  一系列羰基氧化膦配体由 2-溴苯醛合成，并用于铜催化的 CS 偶联反应。在温和的反应条件下，芳基碘和芳基溴与硫醇有效反应，产率高达99%。
• 1-(4-Alkylthiopheny)-2-substituted amino-alcohols and their salts
  申请人：Continental Pharma

  公开号：US03954871A1

  公开（公告）日：1976-05-04

  The new amino-alcohols according to the invention are represented by the formula ##SPC1## Wherein: R.sub.1 represents a RS, RSO or RSO.sub.2 group in which R is a linear or branched alkyl group (C.sub.1 -C.sub.10), an acetyl radical or hydrogen; R.sub.2 and R.sub.3, which may be identical or different, represent a halogen atom or an alkyl (C.sub.1 -C.sub.3), amino, alkylamino (C.sub.1 -C.sub.4), acylamino, nitro, carboxy, carbalkoxy, trifluoromethyl, alkoxy (C.sub.1 -C.sub.4) or alkylthio (C.sub.1 -C.sub.4) radical; R.sub.4 represents hydrogen or a linear or branched alkyl radical containing 1 - 4 carbon atoms; R.sub.5 and R.sub.6, which may be identical or different, represent hydrogen, a substituted or not, linear or branched alkyl (C.sub.1 -C.sub.16) radical, a cycloalkyl (C.sub.5 -C.sub.6) radical, an alkynyl (C.sub.3 -C.sub.4) radical, an alkenyl (C.sub.3 -C.sub.4) radical or a heterocycle of the kind piperidine, morpholine, pyridine or pyridimine, R.sub.5 and R.sub.6 can also form with adjacent nitrogen atom a heterocyclic radical, substituted or not; one of said R.sub.2 and R.sub.3 can be a hydrogen atom or can be both a hydrogen atom provided that simultaneously R is a lower alkyl (C.sub.1 -C.sub.3) radical in the group RS, R.sub.4 and R.sub.5 are hydrogen atoms and R.sub.6 is an isopropyl or t-butyl radical or if simultaneously R is a methyl radical in the group RSO.sub.2, R.sub.4 and R.sub.5 are hydrogen atoms and R.sub.6 is an isopropyl radical. When R.sub.5 and R.sub.6 represent an alkyl, the latter can be substituted by amino, alkylamino, hydroxy, alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl radical or a heterocycle such as piperidino or morpholino.

  根据发明，新的氨基醇可由以下式表示：其中：R.sub.1代表RS、RSO或RSO.sub.2基团，其中R为直链或支链烷基(C.sub.1 -C.sub.10)、乙酰基团或氢原子；R.sub.2和R.sub.3，可能相同也可能不同，代表卤素原子或烷基(C.sub.1 -C.sub.3)、氨基、烷基氨基(C.sub.1 -C.sub.4)、酰胺基、硝基、羧基、羧酸烷氧基、三氟甲基、烷氧基(C.sub.1 -C.sub.4)或烷硫基(C.sub.1 -C.sub.4)基团；R.sub.4代表氢原子或含有1-4个碳原子的直链或支链烷基基团；R.sub.5和R.sub.6，可能相同也可能不同，代表氢原子、取代或非取代的直链或支链烷基(C.sub.1 -C.sub.16)基团、环烷基(C.sub.5 -C.sub.6)基团、炔基(C.sub.3 -C.sub.4)基团、烯基(C.sub.3 -C.sub.4)基团或哌啶、吗啉、吡啶或吡啶咪唑等异环的基团，R.sub.5和R.sub.6也可以与相邻的氮原子形成取代或非取代的杂环基团；其中R.sub.2和R.sub.3中的一个可以是氢原子，或者同时R为RS中的较低烷基(C.sub.1 -C.sub.3)基团时，R.sub.4和R.sub.5为氢原子，R.sub.6为异丙基或叔丁基基团；或者同时R为RSO.sub.2中的甲基基团时，R.sub.4和R.sub.5为氢原子，R.sub.6为异丙基基团。当R.sub.5和R.sub.6代表烷基时，后者可以被氨基、烷基氨基、羟基、烷氧基、苯氧基、取代苯氧基、苯基、取代苯基基团或哌啶啉或吗啉等异环所取代。
• A General Method for the Formation of Aryl−Sulfur Bonds Using Copper(I) Catalysts
  作者：Craig G. Bates、Rattan K. Gujadhur、D. Venkataraman

  DOI：10.1021/ol0264105

  日期：2002.8.1

  [reaction: see text] We report a mild, palladium-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 degrees C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.

  [反应：见正文]我们报道了一种温和，无钯的合成方案，用于在110℃下使用NaOt-Bu为基础，以10 mol％CuI和10 mol％新铜丙氨酸为基础的芳基碘化物和硫醇的交叉偶联反应。使用该协议，我们已经表明，可以从易得的碘化物和硫醇中以优异的产率合成多种芳基硫化物。