6-氟萘-2-甲腈 | 13790-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-氟萘-2-甲腈
• 英文名称: 6-fluoro-2-naphthonitrile
• 英文别名: 6-Fluor-2-cyan-naphthalin；6-fluoronaphthalene-2-carbonitrile
• CAS: 13790-83-5
• 化学式: C₁₁H₆FN
• mdl: MFCD12922839
• 分子量: 171.174
• InChiKey: YVCTUSUDLMFLQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  6-氟萘-2-甲腈 在 硫酸 、 溶剂黄146 作用下， 生成 6-氟-2-萘甲酸
  参考文献：
  名称：

  Substituent Effects. VIII.¹ Synthesis of Substituted α- and β-Fluoronaphthalenes²

  摘要：

  DOI：

  10.1021/ja00978a038
• 作为产物：
  描述：

  在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 0.5h， 以110 mg的产率得到6-氟萘-2-甲腈
  参考文献：
  名称：

  One-Pot, Two-Step, Microwave-Assisted Palladium-Catalyzed Conversion of Aryl Alcohols to Aryl Fluorides via Aryl Nonaflates

  摘要：

  A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.

  DOI：

  10.1021/jo400255m

文献信息

• BIMESOGENIC COMPOUNDS AND MESOGENIC MEDIA
  申请人：Merck Patent GmbH

  公开号：US20170210990A1

  公开（公告）日：2017-07-27

  The invention relates to bimesogenic compounds of formula I wherein R 11 , R 12 , MG 11 , MG 12 , X 11 , X 12 and Sp 1 have the meaning given in claim 1 , to the use of bimesogenic compounds of formula I in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

  这项发明涉及式I的双向嵌段化合物，其中R11、R12、MG11、MG12、X11、X12和Sp1的含义如权利要求1所述，涉及在液晶介质中使用式I的双向嵌段化合物，特别涉及包括根据本发明的液晶介质的柔电液晶器件。
• Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination
  作者：Peng Xu、Priscila López-Rojas、Tobias Ritter

  DOI：10.1021/jacs.1c02490

  日期：2021.4.14

  aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the

  丰富的芳香羧酸存在于自然界和合成中的巨大结构多样性中。迄今为止，苯甲酸的具有合成价值的脱羧官能化主要是通过过渡金属催化的脱羧交叉偶联来实现的。然而，通常需要 140 °C 反应温度的热脱羧碳金属化的高活化能垒限制了底物范围以及可以维持这种条件的合适反应的范围。许多反应，例如，为脂肪族羧酸很好地开发的脱羧氟化，对于芳香族对应物来说，用当前的反应化学是无法实现的。这里，我们报告了一种概念上不同的方法，通过低势垒光诱导配体到金属电荷转移 (LMCT) 启用自由基脱羧碳金属化策略，该策略生成假定的高价芳基铜 (III) 配合物，从中可以发生通用的轻松还原消除。我们证明了我们的新方法适用于解决以前未实现的苯甲酸的一般脱羧氟化。
• Bimesogenic compounds and mesogenic media
  申请人：Merck Patent GmbH

  公开号：US10450508B2

  公开（公告）日：2019-10-22

  The invention relates to bimesogenic compounds of formula I wherein R11, R12, MG11, MG12, X11, X12 and Sp1 have the meaning given in claim 1, to the use of bimesogenic compounds of formula l in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

  本发明涉及式 I 的双巯基化合物 其中 R11、R12、MG11、MG12、X11、X12 和 Sp1 具有权利要求 1 中给出的含义，本发明涉及式 l 的双生化合物在液晶介质中的应用，特别是涉及包含本发明液晶介质的柔电液晶器件。
• Substituent Effects. VIII.¹ Synthesis of Substituted α- and β-Fluoronaphthalenes²
  作者：W. Adcock、M. J. S. Dewar

  DOI：10.1021/ja00978a038

  日期：1967.1
• One-Pot, Two-Step, Microwave-Assisted Palladium-Catalyzed Conversion of Aryl Alcohols to Aryl Fluorides via Aryl Nonaflates
  作者：Johan Wannberg、Charlotta Wallinder、Meltem Ünlüsoy、Christian Sköld、Mats Larhed

  DOI：10.1021/jo400255m

  日期：2013.4.19

  A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.