ethyl α-fluoro-α-[(2-pyrimidyl)thio]acetate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl α-fluoro-α-[(2-pyrimidyl)thio]acetate
• 英文别名: ethyl 2-fluoro-2-(pyrimidin-2-ylthio)acetate；ethyl 2-fluoro-2-(2-pyrimidinylthio)acetate；Ethyl 2-fluoro-2-pyrimidin-2-ylsulfanylacetate
• 化学式: C₈H₉FN₂O₂S
• 分子量: 216.236
• InChiKey: GJMHXUMUKLHOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl α-fluoro-α-[(2-pyrimidyl)thio]acetate 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 ethyl 2-fluoro-2-(pyrimidin-2-ylsulfonyl)acetate
  参考文献：
  名称：

  醛与嘧啶基-氟砜通过Julia-Kocienski反应的（Z）-2-氟链烷酸酯的立体选择形成

  摘要：

  从嘧啶基氟砜报道了氟代链烯酸酯的选择性合成。该砜允许由芳族和脂族醛两者制备具有非常高的立体选择性的Z-氟代链烯酸酯。讨论了Julia-Kocienski反应过程中杂环的性质。

  DOI：

  10.1016/j.tet.2014.06.081
• 作为产物：
  描述：

  ethyl 2-(pyrimidin-2-ylthio)acetate 在 C₂F₆NO₄S₂^(1-)*C₁₃H₁₆IN₂O⁽¹⁺⁾ 、 triethylamine tris(hydrogen fluoride) 作用下， 以87%的产率得到ethyl α-fluoro-α-[(2-pyrimidyl)thio]acetate
  参考文献：
  名称：

  使用特定任务的离子液体进行选择性电催化氟化

  摘要：

  通过使用任务特定的碘芳烃离子液体作为离子液体氟化氢盐的介体，首次成功地进行了有机化合物的高选择性间接阳极氟化。

  DOI：

  10.1021/ol9028836

文献信息

• Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
  作者：Florent Larnaud、Emmanuel Pfund、Bruno Linclau、Thierry Lequeux

  DOI：10.1016/j.tet.2014.06.081

  日期：2014.9

  This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia–Kocienski reaction is discussed.

  从嘧啶基氟砜报道了氟代链烯酸酯的选择性合成。该砜允许由芳族和脂族醛两者制备具有非常高的立体选择性的Z-氟代链烯酸酯。讨论了Julia-Kocienski反应过程中杂环的性质。
• Scope and limitations of the Julia–Kocienski reaction with fluorinated sulfonylesters
  作者：Charlène Calata、Jean-Marie Catel、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1016/j.tet.2009.03.041

  日期：2009.5

  The study of the Julia–Kocienski reaction between fluorinated arylsulfone and ketones is described. The corresponding fluoroalkenes were isolated in moderate to good yields from β- and δ-substituted cyclic ketones. From acyclic ketones and α-substituted cyclic ketones a decarbethoxylation reaction of the sulfonylesters occurred. This decarbethoxylation reaction opened a new route for the preparation

  描述了氟化芳基砜与酮之间的Julia-Kocienski反应的研究。从β-和δ-取代的环酮以中等至良好的产率分离出相应的氟代烯烃。由无环酮和α-取代的环酮发生磺酰基酯的脱碳乙氧基化反应。该脱碳乙氧基化反应为制备各种氟代烷基砜作为制备氟代烯烃的潜在基石开辟了一条新途径。
• Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides
  作者：Kamal M. Dawood、Seiichiro Higashiya、Yankun Hou、Toshio Fuchigami

  DOI：10.1021/jo9909857

  日期：1999.10.1

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.
• Heterocyclization Reagents for Rapid Assembly of N‐Fused Heteroarenes from Alkenes
  作者：Huihui Zhang、Min Wang、Xinxin Wu、Chen Zhu

  DOI：10.1002/anie.202013089

  日期：2021.2.15

  N‐Fused heterocycles are of particular use and upmost importance in multiple fields. Herein, we disclose a conceptually new approach for the rapid assembly of N‐fused heteroarenes from alkenes. A portfolio of strategically designed heterocyclization reagents are readily prepared for the cascade reaction. A plethora of N‐fused heteroarenes including seven types of heterocyclic core are furnished. The

  N-融合杂环在多个领域中具有特殊的用途和最重要的意义。本文中，我们公开了一种从烯烃快速组装N稠合杂芳烃的概念新方法。容易制备用于级联反应的策略性设计的杂环试剂组合。提供了包括7种杂环核在内的大量N稠合杂芳烃。该协议具有广泛的功能组兼容性和较高的产品多样性，并为后期杂芳烃的加工提供了实用工具。
• Use of Task-Specific Ionic Liquid for Selective Electrocatalytic Fluorination
  作者：Takahiro Sawamura、Shunsuke Kuribayashi、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1021/ol9028836

  日期：2010.2.5

  Highly selective indirect anodic fluorination of organic compounds was successfully carried out for the first time by using a task-specific ionic liquid of iodoarene as a mediator in ionic liquid hydrogen fluoride salts.

  通过使用任务特定的碘芳烃离子液体作为离子液体氟化氢盐的介体，首次成功地进行了有机化合物的高选择性间接阳极氟化。