(2-Pyridyl)tetrahydrofurfuryl sulfide

• 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)tetrahydrofurfuryl sulfide
• 英文别名: 2-((tetrahydrofuran-2-yl)methylthio)pyridine；2-(2-tetrahydrofurmethylthio)pyridine；2-(Oxolan-2-ylmethylsulfanyl)pyridine
• 化学式: C₁₀H₁₃NOS
• mdl: MFCD03772791
• 分子量: 195.285
• InChiKey: FJLLOUYSNCCMCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-Pentenyl-1-oxy)pyridine-2(1H)-thione 以 苯 为溶剂， 反应 0.08h， 以64%的产率得到(2-Pyridyl)tetrahydrofurfuryl sulfide
  参考文献：
  名称：

  Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans

  摘要：

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.

  DOI：

  10.1021/jo00126a021

文献信息

• 一种芳基硫醚类化合物的合成方法
  申请人：华东师范大学

  公开号：CN103848767B

  公开（公告）日：2016-08-17

  本发明公开了一种式(3)所示的芳基硫醚类化合物的合成方法，是在反应溶剂中，以芳基碘化物或芳基三氟甲烷磺酸酯类衍生物，与卤代烷烃为反应原料，以Na2S2O3为硫化试剂，在金属钯催化剂作用下，反应得到多取代的芳基硫醚类化合物。本发明反应条件温和，原料易得价廉，反应操作简单，产率较高，为很多天然产物和药物的合成提供关键的骨架结构，可以广泛适用于工业化规模生产。
• SUBSTITUTED ADENINES AND THE USES THEREOF
  申请人：Cavero-Tomas Marta

  公开号：US20090048203A1

  公开（公告）日：2009-02-19

  This invention relates to compounds of Formula (I): and their use in the treatment of bacterial infections.

  本发明涉及式(I)的化合物及其在治疗细菌感染方面的应用。
• Direct Cross-Coupling Access to Diverse Aromatic Sulfide: Palladium-Catalyzed Double C–S Bond Construction Using Na₂S₂O₃ as a Sulfurating Reagent
  作者：Zongjun Qiao、Jianpeng Wei、Xuefeng Jiang

  DOI：10.1021/ol500112y

  日期：2014.2.21

  The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na2S2O3 center dot 5H(2)O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O3 center dot 5H(2)O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.