2-pyridyl 4-cyanophenyl sulfide | 146596-03-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-pyridyl 4-cyanophenyl sulfide
• 英文别名: 4-(2-pyridylthio)benzonitrile；4-Pyridin-2-ylsulfanylbenzonitrile
• CAS: 146596-03-4
• 化学式: C₁₂H₈N₂S
• 分子量: 212.275
• InChiKey: PVLNAAZHHDUZIX-UHFFFAOYSA-N

物化性质

• 沸点：
  410.8±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-pyridyl 4-cyanophenyl sulfide 、 2-萘硫醇 在 bis(acetylacetonate)nickel(II) 、 锰 、 1,3-双(二苯基膦)丙烷 、 lithium tert-butoxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以38%的产率得到4-(naphthalen-2-ylthio)benzonitrile
  参考文献：
  名称：

  Ni催化的芳基2-吡啶基硫醚与烷基和芳基硫醇偶联的C-S键断裂

  摘要：

  已经开发出镍催化的 C-S Py键活化反应来生产各种硫醚。该反应由用户友好、廉价、空气和水分稳定的镍预催化剂促进。各种芳基 2-吡啶基硫醚和范围广泛的烷基和芳基硫醇底物在该过程中是可耐受的，从而以中等至极好的产率提供产品。

  DOI：

  10.1016/j.tet.2021.132453
• 作为产物：
  描述：

  对氯苯甲腈 、 2-巯基吡啶硫醇盐 在 4,4'-联吡啶 作用下， 以 氨 为溶剂， 以90%的产率得到2-pyridyl 4-cyanophenyl sulfide
  参考文献：
  名称：

  Aryl radicals from electrochemical reduction of aryl halides. Addition on olefins

  摘要：

  Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF). The arylated product is obtained in good yield in the latter case. In pure liquid NH3, the yields are extremely poor. They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol. A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments. Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an S(RN)1 substitution process.

  DOI：

  10.1021/jo00002a020

文献信息

• Enforced Electronic‐Donor‐Acceptor Complex Formation in Water for Photochemical Cross‐Coupling
  作者：Ya‐Ming Tian、Evamaria Hofmann、Wagner Silva、Xiang Pu、Didier Touraud、Ruth M. Gschwind、Werner Kunz、Burkhard König

  DOI：10.1002/anie.202218775

  日期：——

  The sugar alcohol meglumine can solubilize organic compounds in water to synthetically useful levels, allowing the formation of enforced electron donor acceptor (EDA) complexes in water. These EDA complexes offer a new activation for light driven C−C and C−S cross-coupling chemistry without sensitizers.

  糖醇葡甲胺可以将水中的有机化合物溶解到合成有用的水平，从而在水中形成强制电子供体受体 (EDA) 复合物。这些 EDA 复合物为光驱动的 C−C 和 C−S 交叉偶联化学提供了一种新的激活，无需敏化剂。
• Dimerization of aryl radicals as a termination step in SRN1 aromatic nucleophilic substitution
  作者：Rofia Ettayeb、Jean Michel Saveant、Andre Thiebault

  DOI：10.1021/ja00053a062

  日期：1992.12
• Ni-catalyzed C–S bond cleavage of aryl 2-pyridyl thioethers coupling with alkyl and aryl thiols
  作者：Cheng-Yi Wang、Rui Tian、Yong-Ming Zhu

  DOI：10.1016/j.tet.2021.132453

  日期：2021.10

  A nickel-catalyzed C–SPy bond activation reactions to produce a variety of thioethers has been developed. The reaction is promoted by a user-friendly, inexpensive, air and moisture-stable Ni precatalyst. Various aryl 2-pyridyl thioethers and a wide range of alkyl and aryl thiols substrates were tolerated in this process which afforded products in moderate to excellent yields.

  已经开发出镍催化的 C-S Py键活化反应来生产各种硫醚。该反应由用户友好、廉价、空气和水分稳定的镍预催化剂促进。各种芳基 2-吡啶基硫醚和范围广泛的烷基和芳基硫醇底物在该过程中是可耐受的，从而以中等至极好的产率提供产品。
• Aryl radicals from electrochemical reduction of aryl halides. Addition on olefins
  作者：Zoubida Chami、Monique Gareil、Jean Pinson、Jean Michel Saveant、Andre Thiebault

  DOI：10.1021/jo00002a020

  日期：1991.1

  Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF). The arylated product is obtained in good yield in the latter case. In pure liquid NH3, the yields are extremely poor. They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol. A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments. Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an S(RN)1 substitution process.