(4-fluoro-4-methylpiperidin-1-yl)(phenyl)methanone | 1383116-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-fluoro-4-methylpiperidin-1-yl)(phenyl)methanone
• 英文别名: (4-Fluoro-4-methylpiperidin-1-yl)-phenylmethanone
• CAS: 1383116-17-3
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: VTHDBTTWVXHZGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-benzoyl-4-methylpiperidine-4-carboxylic acid 在 silver nitrate 、 Selectfluor 作用下， 以 水 、 丙酮 为溶剂， 反应 10.0h， 以76%的产率得到(4-fluoro-4-methylpiperidin-1-yl)(phenyl)methanone
  参考文献：
  名称：

  脂肪族羧酸在水溶液中的银催化脱羧氟化

  摘要：

  尽管氟化化合物已在化学和材料行业中得到广泛应用，但一般和特定于站点的 C(sp(3))-F 键的形成仍然是一项具有挑战性的任务。我们在此报告，在 AgNO(3) 的催化作用下，各种脂肪族羧酸在水溶液中使用 SELECTFLUOR(®) 试剂进行有效的脱羧氟化，从而在温和条件下以令人满意的产率合成相应的烷基氟化物。这种自由基氟化方法不仅高效通用，而且具有化学选择性和官能团相容性，因此在氟化分子的合成中具有很高的实用性。对于这种催化氟脱羧，提出了一种涉及 Ag(III) 介导的单电子转移，然后是氟原子转移的机制。

  DOI：

  10.1021/ja3048255

文献信息

• Synthesis of Alkyl Fluorides by Silver‐Catalyzed Radical Decarboxylative Fluorination of Cesium Oxalates
  作者：Émilie Vincent、Julien Brioche

  DOI：10.1002/ejoc.202100344

  日期：2021.5.7

  Readily available from alcohols, cesium oxalates undergo radical deoxyfluorination reaction in the presence of silver salts catalyst and Selectfluor® to produce alkyl fluorides. Herein, the scope of the fluorination protocol and a brief mechanistic study is described.

  草酸铯很容易从醇中获得，在银盐催化剂和Selectfluor®存在下进行自由基脱氧氟化反应，生成烷基氟化物。在此，描述了氟化方案的范围和简要的机理研究。
• One-pot synthesis of tertiary alkyl fluorides from methyl oxalates by radical deoxyfluorination under photoredox catalysis
  作者：Julien Brioche

  DOI：10.1016/j.tetlet.2018.10.063

  日期：2018.12

  Tertiary alkyl fluorides have been prepared from methyl oxalates derived from tertiary alcohols by a sequential one-pot hydrolysis/photoredox catalyzed radical deoxyfluorination sequence. The reaction operates under mild conditions and tolerates a wide range of functional groups. This method provides an alternative approach to ionic deoxyfluorination transformations for the incorporation of Carbone–Fluorine

  叔烷基氟化物已经由叔醇衍生的草酸甲酯通过顺序的一锅水解/光氧化还原催化的自由基脱氧氟序列制备。该反应在温和的条件下进行，并能耐受各种官能团。该方法为将Carbone-Fluorine季中心引入有机分子中提供了另一种方法来进行离子脱氧氟化转化。
• Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis
  作者：Sandrine Ventre、Filip R. Petronijevic、David W. C. MacMillan

  DOI：10.1021/jacs.5b02244

  日期：2015.5.6

  The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer

  通过可见光促进的光氧化还原催化，实现了脂肪族羧酸直接转化为相应的烷基氟化物。这种操作简单、氧化还原中性的氟化方法适用于多种羧酸。光子诱导的羧酸盐氧化导致羧基自由基的形成，通过快速CO2挤出和氟化试剂的F(·)转移，高效地产生所需的氟代烷烃。实验证据表明，氧化猝灭途径在这种广泛适用的氟化方案中是可行的。
• Decarboxylative cross-coupling and applications thereof
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：US10538509B2

  公开（公告）日：2020-01-21

  Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

  本文所述的方法可通过使用光氧化还原和过渡金属催化剂进行脱羧交叉偶联来生产多种分子物质。在某些实施方案中，本文所述的方法包括提供一种反应混合物，其中包括一种光氧化催化剂、一种过渡金属催化剂、一种偶联剂和一种具有羧基的基质。用辐射源照射反应混合物，通过包括脱羧在内的机理使基质和偶联剂发生交叉偶联，其中偶联剂选自由取代的芳香族化合物和取代的脂肪族化合物组成的组。
• DECARBOXYLATIVE CROSS-COUPLING AND APPLICATIONS THEREOF
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：US20170022185A1

  公开（公告）日：2017-01-26

  Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. For example, methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.