2-(((4-methoxyphenyl)thio)methyl)pyridine | 83782-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(((4-methoxyphenyl)thio)methyl)pyridine
• 英文别名: 2-[(4-methoxyphenyl)sulfanylmethyl]pyridine
• CAS: 83782-18-7
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: ZOHHIIYZLSACBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(((4-methoxyphenyl)thio)methyl)pyridine 、 2-(4-溴苯基)-2-重氮基乙酸乙酯 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 作用下， 以 乙酸乙酯 为溶剂， 以77%的产率得到ethyl 2-(4-bromo-2-(((4-methoxyphenyl)thio)(pyridin-2-yl)methyl)phenyl)acetate
  参考文献：
  名称：

  溶剂依赖的铑催化的硫酰化物的重排反应†

  摘要：

  苄基硫醚与芳基重氮乙酸酯进行铑（II）催化的σ重排反应。取决于溶剂和硫化物的电子性质，中间体叶立德以高收率进行[1,2]-或[2,3]-σ重排反应。

  DOI：

  10.1039/c9cc03809d
• 作为产物：
  描述：

  2-吡啶甲醇 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 2-(((4-methoxyphenyl)thio)methyl)pyridine
  参考文献：
  名称：

  Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines

  摘要：

  We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 degrees C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.

  DOI：

  10.1021/acs.joc.9b00871

文献信息

• Metal- and base-free regioselective thiolation of the methyl C(sp³)–H bond in 2-picoline <i>N</i>-oxides
  作者：Dong Wang、Zhenlin Liu、Zhentao Wang、Xinyue Ma、Peng Yu

  DOI：10.1039/c8gc03072c

  日期：——

  A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)–H bond in 2-picolines with thiols. Remarkable features of the method

  通过TFAA介导的吡啶N-氧化物的[3,3]-σ重排和TBAB催化的三氟乙酸盐在金属和金属催化下直接转化为三氟乙酸的反应，可以开发一锅两步的吡啶-2-基甲基硫醚合成方法无碱条件。这种方法可以使未活化的甲基C（sp 3硫醇化）–2-甲基吡啶与硫醇的氢键。该方法的显着特征包括区域选择性高，阶跃和原子经济，条件温和，操作简单，底物范围广和可扩展性。此外，该方法已成功地用于合成奥美拉唑硫化物和雷贝拉唑硫化物，而无需TBAB催化。全面的绿色化学指标分析表明，该方法比报道的雷贝拉唑硫化物更有效，更环保。
• 2-[(Phenylthio)methyl]pyridine derivatives: new antiinflammatory agents
  作者：Fortuna Haviv、Robert W. DeNet、Raymond J. Michaels、James D. Ratajczyk、George W. Carter、Patrick R. Young

  DOI：10.1021/jm00356a018

  日期：1983.2

  2-[(Phenylthio)methyl]pyridine derivatives inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat. In the same model, indomethacin was inactive, and hydrocortisone was active. Compounds Ia-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin

  2-[（（苯硫基）甲基]吡啶衍生物可抑制大鼠皮肤逆向被动Arthus反应（RPAR）。在同一模型中，消炎痛是无活性的，氢化可的松是有活性的。化合物Ia-d还显着减少了胸膜RPAR中的渗出液量和白细胞积聚。这种活性模式与氢化可的松相似，与消炎痛不同。
• Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines
  作者：Filipe Penteado、Caroline S. Gomes、Gelson Perin、Cleisson S. Garcia、Cristiani F. Bortolatto、César A. Brüning、Eder J. Lenardão

  DOI：10.1021/acs.joc.9b00871

  日期：2019.6.7

  We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 degrees C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.
• Solvent-dependent, rhodium catalysed rearrangement reactions of sulfur ylides
  作者：Zhen Yang、Yujing Guo、Rene M. Koenigs

  DOI：10.1039/c9cc03809d

  日期：——

  Benzyl thioethers undergo rhodium(II) catalyzed sigmatropic rearrangement reactions with aryldiazoacetates. Depending on the solvent and the electronic properties of the sulfide, the intermediate ylide undergoes either [1,2]- or [2,3]-sigmatropic rearrangement reactions in high yields.

  苄基硫醚与芳基重氮乙酸酯进行铑（II）催化的σ重排反应。取决于溶剂和硫化物的电子性质，中间体叶立德以高收率进行[1,2]-或[2,3]-σ重排反应。