4,4'-(azidomethylene)bis(fluorobenzene) | 1093981-40-8

• 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: 4,4'-(azidomethylene)bis(fluorobenzene)
• 英文别名: 1-[azido-(4-fluorophenyl)methyl]-4-fluorobenzene
• CAS: 1093981-40-8
• 化学式: C₁₃H₉F₂N₃
• 分子量: 245.231
• InChiKey: VJAYSYZJTKXCGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,4'-(azidomethylene)bis(fluorobenzene) 在 水 、 苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以87%的产率得到4-氟-N-(4-氟苯基)苯甲酰胺
  参考文献：
  名称：

  An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C–C Bond Cleavage

  摘要：

  A novel iron-catalyzed transformation of benzyl azides to give the corresponding amides via C-C bond cleavage under mild reaction conditions is developed. This method provides a new synthetic tool for the construction of amides and the opportunity to accomplish C-C functionalization under mild conditions.

  DOI：

  10.1055/s-0034-1380222
• 作为产物：
  描述：

  4,4'-二氟二苯甲烷 在 叠氮基三甲基硅烷 、 copper diacetate 、 2,2′-双[(4S)-4-苄基-2-噁唑啉] 、 N-氟代双苯磺酰胺 作用下， 以 硝基甲烷 为溶剂， 反应 48.0h， 以60%的产率得到4,4'-(azidomethylene)bis(fluorobenzene)
  参考文献：
  名称：

  Site-Selective Copper-Catalyzed Azidation of Benzylic C–H Bonds

  摘要：

  Site selectivity represents a key challenge for non-directed C-H functionalization, even when the C-H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C-H azidation of diverse molecules. Experimental and density functional theory studies suggest the benzyl radical reacts with a Cu-II-azide species via a radical-polar crossover pathway. Comparison of this method with other C-H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target molecule synthesis and medicinal chemistry.

  DOI：

  10.1021/jacs.0c05362

文献信息

• Efficient synthesis of carbonyl compounds: oxidation of azides and alcohols catalyzed by vanadium pentoxide in water using tert-butylhydroperoxide
  作者：Kaliyamoorthy Alagiri、Kandikere Ramaiah Prabhu

  DOI：10.1016/j.tet.2011.08.080

  日期：2011.11

  tert-butylhydroperoxide combination turned out to be an effective catalyst for the oxidation of alcohols. Using vanadium pentoxide and aq tert-butylhydroperoxide primary alcohols were oxidized to the corresponding acids, whereas secondary alcohols underwent a smooth transformation to furnish corresponding ketones in excellent yields. All the oxidations are performed in water.

  发现叔丁基氢过氧化物作为氧化剂的钒试剂的催化量在水性介质中是极好的氧化剂。五氧化二钒与叔丁基过氧化氢水溶液很容易将伯苄基叠氮化物氧化成相应的酸，将仲苄基叠氮化物氧化成相应的酮，产率很高。此外，五氧化二钒和叔丁基过氧化氢水溶液的组合被证明是醇氧化的有效催化剂。使用五氧化二钒和水溶液叔叔丁基过氧化氢伯醇被氧化成相应的酸，而仲醇则经历了平滑的转化，以优异的收率提供了相应的酮。所有氧化均在水中进行。
• A combination of trimethylsilyl chloride and hydrous natural montmorillonite clay: an efficient solid acid catalyst for the azidation of benzylic and allylic alcohols with trimethylsilyl azide
  作者：Michael A. Tandiary、Yoichi Masui、Makoto Onaka

  DOI：10.1039/c4ra13238f

  日期：——

  We present a new procedure to convert in situ natural montmorillonite clay into a partially acidified one using a catalytic amount of trimethylsilyl chloride and trace water.

  我们提出了一种新的程序，使用少量的三甲基氯硅烷和微量水将原位天然蒙脱石粘土部分酸化。
• Direct AlCl₃-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers
  作者：Tien Tan Bui、Hee-Kwon Kim

  DOI：10.1080/00397911.2020.1829644

  日期：2021.2.1

  THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are r...

  THP 和烯丙基经常用于保护醇。在这项研究中，苄基 THP 醚和烯丙基苄基醚（醇的保护形式）的新型直接转化是...
• Facile Direct Coupling Reactions of <scp>MOM</scp> ‐protected Benzylic Alcohols Using Aluminum Chloride
  作者：Tien Tan Bui、Hee‐Kwon Kim

  DOI：10.1002/bkcs.12358

  日期：2021.9

  used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results

  MOM 基团是最常用的醇类保护基团之一。本研究描述了 MOM 保护的苯甲醇的新型直接功能化。利用烯丙基三甲基硅烷和AlCl 3成功地从苄基MOM醚制备烯丙基化合物。此外，在AlCl 3介导的反应条件下，使用TMSN 3成功地进行了苄基MOM 醚的直接叠氮化。这些结果表明，这种新的合成程序是一种有前途的方法，可以直接将 MOM 保护的醇官能化，包括烯丙基化和叠氮化。
• Indium(III) bromide catalyzed direct azidation of α-hydroxyketones using TMSN3
  作者：Anil Kumar、Ramesh K. Sharma、Tej V. Singh、Paloth Venugopalan

  DOI：10.1016/j.tet.2013.10.055

  日期：2013.12

  The direct catalytic azidation of 2-hydroxy-1,2,2-triarylethanones occurs at room temperature using 2 mol % of InBr3 as Lewis acid and TMSN3 as soluble azide source. 2-Azido-1,2,2-triarylethanones have been isolated in excellent yields. The role of aryl group and stereoelectronic factors indicate that the mechanism may involve the formation of a stable carbenium ion towards azidation. (C) 2013 Elsevier Ltd. All rights reserved.