4-Fluoro-2-methylquinoline | 703-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-Fluoro-2-methylquinoline
• 英文别名: 4-fluoroquinaldine；4-Fluorquinaldin；Quinoline, 4-fluoro-2-methyl-
• CAS: 703-62-8
• 化学式: C₁₀H₈FN
• mdl: MFCD18803126
• 分子量: 161.179
• InChiKey: IHACCDXTDLQSJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Fluoro-2-methylquinoline 在 水 、 溶剂黄146 、 sodium chloride 作用下， 生成 4-羟基-2-甲基喹啉
  参考文献：
  名称：

  Hydrolyses of 2- and 4-fluoro N-heterocycles. 3. Nucleophilic catalysis by buffer bases in the general-acid-catalyzed hydrolysis of 4-fluoroquinaldine

  摘要：

  DOI：

  10.1021/jo00262a037
• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 PhenoFluor 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到4-Fluoro-2-methylquinoline
  参考文献：
  名称：

  PhenoFluorMix: Practical Chemoselective Deoxyfluorination of Phenols

  摘要：

  A practical deoxyfluorination with novel deoxyfluorinating reagent PhenoFluorMix, a mixture of N,N'-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF, is presented. PhenoFluorMix overcomes the challenges associated with hydrolysis of PhenoFluor. PhenoFluorMix does not hydrolyze, is readily available on decagram scale, and is storable in air. In this paper, we demonstrate the practicality of the reagent and exhibit the deoxyfluorination of a variety of phenols and heterocycles.

  DOI：

  10.1021/ol5035518

文献信息

• Bicyclic cyclohexylamines and their use as nmda receptor antagonists
  申请人：——

  公开号：US20030236252A1

  公开（公告）日：2003-12-25

  Described are bicycle-substituted cyclohexylamines of Formula (I) and their pharmaceutically acceptable salts thereof. The compounds are antagonists of NMDA receptor channel complexes useful for treating cerebral vascular disorders such as, for example, cerebral ischemia, cardiac arrest, stroke, and Parkinson's specification. disease. The substituents are defined in the specification. 1

  描述了公式（I）的自行车替代环己胺及其药用盐。这些化合物是NMDA受体通道复合物的拮抗剂，可用于治疗脑血管疾病，例如脑缺血、心脏骤停、中风和帕金森病。这些取代基在规范中有定义。
• Cyclohexylamine derivatives as subtype selective nmda receptor antagonists
  申请人：——

  公开号：US20030225164A1

  公开（公告）日：2003-12-04

  Described are cyclohexylamine derivatives of Formula (I), Formula (II) or Formula (III) and their pharmaceutically acceptable salts thereof. The compounds are antagonists of NMDA receptor channel complexes useful for treating cerebral vascular disorders such as, for example, cerebral ischemia, cardiac arrest, stroke, and Parkinson's disease. The substituents are described in the specification. 1

  描述了公式(I)、公式(II)或公式(III)的环己胺衍生物及其药学上可接受的盐。这些化合物是NMDA受体通道复合物的拮抗剂，可用于治疗脑血管疾病，例如脑缺血、心脏骤停、中风和帕金森病。取代基在说明书中有描述。
• Cyclohexylamine derivative as subtype selective nmda receptor antagonists
  申请人：——

  公开号：US20030236286A1

  公开（公告）日：2003-12-25

  Described are compounds of Formula I and Formula II and their pharmaceutically acceptable salts. The compounds of Formulas I and II are antagonists of NMDA receptor channel complexes useful for treating cerebral vascular disorders such as, for example, cerebral ischemia, cardiac arrest, stroke, and Parkinson's disease. 1

  描述了公式I和公式II的化合物及其药学上可接受的盐。公式I和II的化合物是NMDA受体通道复合物的拮抗剂，可用于治疗脑血管疾病，例如脑缺血、心脏停搏、中风和帕金森病。
• Accelerating Palladium-Catalyzed CF Bond Formation: Use of a Microflow Packed-Bed Reactor
  作者：Timothy Noël、Thomas J. Maimone、Stephen L. Buchwald

  DOI：10.1002/anie.201104652

  日期：2011.9.12

  A flow process for Pd‐catalyzed CF bond formation is described. A microreactor with a packed‐bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted into aryl fluorides in short reaction

  描述了 Pd 催化的C F 键形成的流动过程。具有填充床设计的微反应器可以通过精确控制反应时间、有效混合以及安全处理高温和高压的能力轻松处理大量不溶性 CsF。各种芳基三氟甲磺酸酯，包括杂芳基三氟甲磺酸酯，在很短的反应时间内被转化为芳基氟化物（参见方案）。
• Electron-Transfer-Enabled Concerted Nucleophilic Fluorination of Azaarenes: Selective C–H Fluorination of Quinolines
  作者：Li Zhang、Jiyao Yan、Dilgam Ahmadli、Zikuan Wang、Tobias Ritter

  DOI：10.1021/jacs.3c07119

  日期：2023.9.20

  Direct C–H fluorination is an efficient strategy to construct aromatic C–F bonds, but the cleavage of specific C–H bonds in the presence of other functional groups and the high barrier of C–F bond formation make the transformation challenging. Progress for the electrophilic fluorination of arenes has been reported, but a similar transformation for electron-deficient azaarenes has remained elusive due

  直接C-H氟化是构建芳香族C-F键的有效策略，但在其他官能团存在的情况下特定C-H键的断裂以及C-F键形成的高势垒使得转化具有挑战性。芳烃亲电氟化的进展已有报道，但由于相应的 Wheland 中间体的高能量，缺电子氮杂芳烃的类似转化仍然难以实现。由于氟化物攻击后迈森海默中间体的特性，缺电子氮杂芳烃的亲核氟化是困难的，其中氟化物消除以再生底物比氢化物消除形成产物更有利。在此，我们报告了一种新概念，即通过异步协同 F – -e – -H +转移的链式过程，不形成氮杂芳烃 Meisenheimer 中间体的 C–H 亲核氟化。协调一致的亲核芳族取代策略使得喹啉首次成功发生亲核氧化氟化。