4-fluorophenanthridine | 1338060-87-9

• 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-fluorophenanthridine
• CAS: 1338060-87-9
• 化学式: C₁₃H₈FN
• 分子量: 197.212
• InChiKey: FYDXYEATRMTGRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-fluorophenanthridine 、 [1-(2,2,3,3,3-pentafluoropropyl)piperidin-4-yl]methanol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以190 mg的产率得到4-fluoro-6-[[1-(2,2,3,3,3-pentafluoropropyl)piperidin-4-yl]methoxy]phenanthridine
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061
• 作为产物：
  描述：

  4-fluorophenanthridin-6(5H)-one 在 三氯氧磷 作用下， 生成 4-fluorophenanthridine
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061

文献信息

• Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-<i>N</i>-Ms-arylamines with Benzyl Halides/Sulfonates
  作者：Si-Yi Yang、Wen-Yong Han、Ding-Lei Zhang、Xiao-Jian Zhou、Mei Bai、Bao-Dong Cui、Nan-Wei Wan、Wei-Cheng Yuan、Yong-Zheng Chen

  DOI：10.1002/ejoc.201601608

  日期：2017.2.3

  An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach

  已经描述了容易获得的 2-卤代-N-Ms-芳基胺（Ms = 甲磺酰基）和苄基卤化物/磺酸盐之间的有效钯催化亲核取代/C-H 活化/芳构化级联反应。以一锅法以中等至高产率 (37–86%) 合成了多种菲啶。值得注意的是，该方法为菲啶的合成提供了一种直接、简便的方法。通过成功进行克级制备进一步证实了实用性。
• Synthesis of Phenanthridines through Iodine-Supported Intramolecular C–H Amination and Oxidation under Visible Light
  作者：Yan Gao、Yi Jing、Lixin Li、Jie Zhang、Xuenian Chen、Yan-Na Ma

  DOI：10.1021/acs.joc.0c01390

  日期：2020.10.2

  Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C–H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.

  在这里，我们报告了在温和的条件下从2-biarylmethanamines无金属和经济的步骤合成菲啶。该反应包括碘在空气和良性可见光下的分子内CH–H胺化和5,6-二氢菲啶的氧化。机制研究表明，可见光在这两个步骤中都起着关键作用。
• One‐pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C−H Oxidation/Aromatization
  作者：Yi Zhang、Yuxin Ding、Rener Chen、Yongmin Ma

  DOI：10.1002/adsc.202000949

  日期：2020.12.22

  A one‐pot cascade coupling/annulation reaction for the synthesis of phenanthridines has been developed from arylboronic acids and o‐bromo arylamides with DMSO as a carbon source. The desired phenanthridines were obtained in moderate to good yields by using simple procedure.

  由芳基硼酸和邻溴代芳基酰胺以DMSO为碳源开发了一种单锅级联偶联/环化反应，用于合成菲啶。通过使用简单的方法，以中等至良好的产率获得了所需的菲啶。
• Catalytic Oxidative Cyclization of 2′-Arylbenzaldehyde Oxime Ethers under Photoinduced Electron Transfer Conditions
  作者：Julie L. Hofstra、Brittany R. Grassbaugh、Quan M. Tran、Nicholas R. Armada、H. J. Peter de Lijser

  DOI：10.1021/jo502324z

  日期：2015.1.2

  sequence is initiated by an electron transfer step followed by nucleophilic attack of the aryl ring onto the nitrogen of the oxime ether. A concave downward Hammett plot is presumably the result of a change in charge distribution in the radical cation species with strongly electron-donating substituents that yields a less electrophilic nitrogen atom and a decreased amount of cyclized product. The reaction

  合成了一系列2'-芳基苯甲醛肟醚，显示出在9,10-二氰基蒽存在下于乙腈中照射后生成相应的菲啶。机理研究表明，氧化环化反应顺序是由电子转移步骤引发的，随后芳基环发生亲核性攻击，并与肟醚的氮原子发生反应。向下凹的哈米特图可能是具有强给电子取代基的自由基阳离子物种中电荷分布变化的结果，该变化产生了较少的亲电子氮原子并减少了环化产物的量。该反应具有选择性（与涉及醛肟醚的其他光化学反应不同，不会形成腈副产物），并且在使用带有2'-芳基的化合物时具有区域特异性间取代基，使该反应成为制备取代的菲啶的有用替代方法。
• Synthesis of Phenanthridine Derivatives via Photolysis
  作者：Anna M. Linsenmeier、Craig M. Williams、Stefan Bräse

  DOI：10.1021/jo201542x

  日期：2011.11.4

  An improved photochemical method for producing the prolifically bioactive phenanthridine system is reported. A wide variety of derivatives were obtained in two steps in yields ranging from 31 to 95%.