(naphthalen-3-yl)(naphthalen-4-yl)sulfane | 62393-34-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (naphthalen-3-yl)(naphthalen-4-yl)sulfane
• 英文别名: naphthalen-1-yl(naphthalen-2-yl)sulfane；[1]naphthyl-[2]naphthyl sulfide；α.β-Dinaphthylsulfid；[1]Naphthyl-[2]naphthyl-sulfid；1-Naphthyl-2-naphthylsulfid；Naphthalene, 1-(2-naphthalenylthio)-；1-naphthalen-2-ylsulfanylnaphthalene
• CAS: 62393-34-4
• 化学式: C₂₀H₁₄S
• 分子量: 286.397
• InChiKey: CHQNATAAAQFKNG-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  487.0±14.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (naphthalen-3-yl)(naphthalen-4-yl)sulfane 在 铬酸 作用下， 生成 1,2-dinaphthylsulfone
  参考文献：
  名称：

  Krafft, Chemische Berichte, 1890, vol. 23, p. 2363

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴代萘 、 2-萘硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以50%的产率得到(naphthalen-3-yl)(naphthalen-4-yl)sulfane
  参考文献：
  名称：

  无配体的固体负载钯（0）纳米/微粒促进了C–O，C–S和C–N交叉偶联反应

  摘要：

  Pd（0）（SS-Pd）的无配体固体负载纳米和微粒在碳-杂原子键形成反应中用作多相催化剂。硝基取代的芳基卤化物与氧，硫和氮亲核试剂反应，以高收率提供相应的产物。还使用相同的SS-Pd催化剂进行一锅顺序交叉偶联和硝基还原，以访问胺取代的碳-杂原子分子。此外，SS-Pd最多可循环使用七次，而不会显着降低催化活性。

  DOI：

  10.1016/j.tetlet.2012.07.096

文献信息

• Forging C–S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation
  作者：Jing-Ya Zhou、Shou-Wei Tao、Rui-Qing Liu、Yong-Ming Zhu

  DOI：10.1021/acs.joc.9b01746

  日期：2019.9.20

  A nickel-catalyzed decarbonylation or decarbonylation accompanied by decarboxylation cross-coupling reaction of aryl anhydrides with thiophenols as coupling partners was disclosed. This method is promoted by a commercially available, moisture-stable, and inexpensive nickel(II) precatalyst. The process can tolerate a variety of functional groups using ubiquitous aryl anhydrides as cross-coupling precursors

  公开了镍催化的脱羰或脱羰，伴随着芳基酸酐与硫酚作为偶联伙伴的脱羧交叉偶联反应。这种方法是由市售的，水分稳定且廉价的镍（II）预催化剂促进的。使用普遍存在的芳基酸酐作为交联前体，该方法可以耐受各种官能团，从而以中等至极好的收率生产硫醚。
• Regiochemistry of the coupling of aryl radicals with nucleophiles derived from the naphthyl system. Experimental and theoretical studies
  作者：Adriana B. Pierini、Maria T. Baumgartner、Roberto A. Rossi

  DOI：10.1021/jo00002a019

  日期：1991.1

  We here report the photostimulated reaction of unactivated aromatic halides with ambident nucleophiles derived from the naphthyl system such as 1- and 2-naphthylamide, 2-naphthoxide, 2-naphthalenethiolate, and 2-naphthaleneselenate ions, by the S(RN)1 mechanism of nucleophilic substitution. According to our experimental results, C-arylation in position 1 of the naphthyl moiety is the only reaction observed with 2-naphthoxide ions and it is favored over N-arylation with 1- and 2-naphthylamide ions. Heteroatom arylation is preferred over C-arylation with 2-naphthalenethiolate ions while it is the only observed reaction with 2-naphthaleneselenate ions. A theoretical study was carried out to explain the regiochemistry of the system. In competition experiments, 2-naphthalenethiolate ions proved to be 1.8 +/- 0.2 times more reactive than 2-naphthoxide ions for C-substitution toward p-anisyl radicals in liquid ammonia.
• KATRITZKY, ALAN R.;MURUGAN, RAMIAH;SISKIN, MICHAEL, ENERGY AND FUELS, 4,(1990) N, C. 577-584
  作者：KATRITZKY, ALAN R.、MURUGAN, RAMIAH、SISKIN, MICHAEL

  DOI：——

  日期：——
• PIERINI, ADRIANA B.;BAUMGARTNER, MARIA T.;ROSSI, ROBERTO A., J. ORG. CHEM., 56,(1991) N, C. 580-586
  作者：PIERINI, ADRIANA B.、BAUMGARTNER, MARIA T.、ROSSI, ROBERTO A.

  DOI：——

  日期：——
• Ligand-free solid supported palladium(0) nano/microparticles promoted C–O, C–S, and C–N cross coupling reaction
  作者：Bandna、Nitul Ranjan Guha、Arun K. Shil、Dharminder Sharma、Pralay Das

  DOI：10.1016/j.tetlet.2012.07.096

  日期：2012.9

  Ligand-free solid-supported nano and microparticles of Pd(0) (SS-Pd) were used as a heterogeneous catalyst in carbon-heteroatom bond formation reactions. Nitro substituted aryl halides reacted with oxygen, sulfur, and nitrogen nucleophiles to afford the corresponding products in good yields. A one-pot sequential cross coupling and nitro-reduction was also performed using the same SS-Pd catalyst to

  Pd（0）（SS-Pd）的无配体固体负载纳米和微粒在碳-杂原子键形成反应中用作多相催化剂。硝基取代的芳基卤化物与氧，硫和氮亲核试剂反应，以高收率提供相应的产物。还使用相同的SS-Pd催化剂进行一锅顺序交叉偶联和硝基还原，以访问胺取代的碳-杂原子分子。此外，SS-Pd最多可循环使用七次，而不会显着降低催化活性。