2,2-difluoro-2-iodo-N-phenylacetamide | 1239497-26-7

• 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: 2,2-difluoro-2-iodo-N-phenylacetamide
• CAS: 1239497-26-7
• 化学式: C₈H₆F₂INO
• 分子量: 297.043
• InChiKey: LZBGKROJQKENES-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  312.8±42.0 °C(Predicted)
• 密度：
  1.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-2-iodo-N-phenylacetamide 在 铜 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以74%的产率得到2,2,3,3-tetrafluoro-N(1),N(4)-diphenylsuccinamide
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions

  摘要：

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.

  DOI：

  10.1021/jo1005262
• 作为产物：
  描述：

  1,1-difluoro-2-oxo-2-(phenylamino)ethane-1-sulfonyl fluoride 在 碳酸氢钠 、 sodium sulfite 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 反应 2.0h， 以76%的产率得到2,2-difluoro-2-iodo-N-phenylacetamide
  参考文献：
  名称：

  Rational and practical synthesis of α,α-difluoro-γ-lactams

  摘要：

  Treatment of N-phenyl-iododifluoroacetamide (1) with terminal alkenes (2) in the presence of Na2S2O4 and NaHCO3 in CH3CN/H2O gave good yields of N-phenyl-2,2-difluoro-4-iodoalkanamide (3), which cyclized under strong basic conditions to afford N-phenyl-alpha,alpha-difluoro-gamma-lactams (4). Or simply, these lactams 4 can be directly prepared in one-pot from 1 and 2 in the presence of Na2S2O4 and NaOH. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.10.013

文献信息

• Cascade Photoredox/Iodide Catalysis: Access to Difluoro-γ-lactams via Aminodifluoroalkylation of Alkenes
  作者：Muliang Zhang、Weipeng Li、Yingqian Duan、Pan Xu、Songlin Zhang、Chengjian Zhu

  DOI：10.1021/acs.orglett.6b01515

  日期：2016.7.1

  iodide salts play a vital role in this reaction, which could tune carbocation reactivity through reversible C–I bond formation for controlling reaction selectivity, and a series of competitive reactions are completely eliminated in the presence of multiple reactivity pathways. The present dual catalytic protocol affords a very convenient method for direct synthesis of various difluoro-γ-lactams from simple

  新颖的级联光氧化还原/碘化物催化系统使烯烃能够用作能够实​​现烯烃的氨基二氟烷基化的自由基受体。廉价的碘盐在该反应中起着至关重要的作用，它可以通过可逆的C–I键形成来调节碳正离子反应性，以控制反应的选择性，并且在存在多个反应性途径的情况下，一系列竞争性反应被完全消除。本双重催化方案为在温和的反应条件下由简单易得的起始原料直接合成各种二氟-γ-内酰胺提供了一种非常方便的方法。
• Visible Light-Promoted Phosphine-Catalyzed Difluoroalkylation of Arenes and Heterocycles
  作者：Heng Lu、Dong-yu Wang、Ao Zhang

  DOI：10.1021/acs.joc.9b02882

  日期：2020.1.17

  A visible light-promoted difluoroalkylation reaction of arenes or heterocycles, using triaryl phosphine as the catalyst and difluoroalkyl iodide as the alkylating agent, is presented. The strategy is highlighted by photocatalyst-free, mild reaction conditions and a broad substrate scope. Mechanistic experiments indicate that this reaction involves a radical-chain process that is initiated by an electron

  提出了使用三芳基膦作为催化剂和二氟烷基碘化物作为烷基化剂的芳烃或杂环的可见光促进的二氟烷基化反应。无光催化剂，温和的反应条件和广泛的底物范围突出了该策略。机理实验表明，该反应涉及自由基链过程，该自由基链过程由二氟烷基碘和膦形成的电子供体-受体配合物引发。
• Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides
  作者：Satenik Mkrtchyan、Michał Jakubczyk、Suneel Lanka、Michael Pittelkow、Viktor O. Iaroshenko

  DOI：10.3390/molecules26102957

  日期：——

  copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully

  我们描述了一种以机制为导向的合成方法发现，该方法能够利用铜催化的直接芳基化从 2-溴-2,2-二氟乙酰胺制备芳香酰胺。使用易于获得且结构简单的芳基前体，例如芳基硼酸、芳基三烷氧基硅烷和二甲基芳基锍盐作为芳基取代基的来源。测试了反应的范围，并且反应对芳基的电子性质不敏感，因为富电子和缺电子的芳基都被成功引入。多种 2-溴-2,2-二氟乙酰胺（作为脂肪族或芳香族仲酰胺或叔酰胺）在开发的条件下也具有反应性。所描述的合成方案显示出优异的效率，并成功用于以良好到优异的产率快速制备各种芳香酰胺。反应规模扩大至克级。
• Phototriggered Fluoroalkylation/Cyclization of Unactivated 1-Acryloyl-2-cyanoindoles: Synthesis of RCOCF₂-Substituted Pyrrolo[1,2-<i>a</i>]indolediones
  作者：Weixian Lv、Pengyuan Yang、Jinwei Yuan、Jiayi Li、Mengran Liang、Yitong Liu、Dongliang Xing、Liangru Yang

  DOI：10.1021/acs.joc.3c02986

  日期：2024.3.1

  A photochemical approach toward RCOCF2-substituted pyrrolo[1,2-a]indolediones was developed by the radical cascade difluoroalkylation/cyclization reaction of unactivated 1-acryloyl-2-cyanoindoles with ethyl iododifluoroacetate or iododifluoramides under visible-light irradiation. This transition-metal- and photosensitizer-free protocol afforded diverse difluoroalkylated pyrrolo[1,2-a]indolediones in

  通过未活化的1-丙烯酰基-2-氰基吲哚与碘二氟乙酸乙酯或碘二氟酰胺在可见光照射下的自由基级联二氟烷基化/环化反应，开发了一种制备RCOCF 2 -取代的吡咯并[ 1,2 -a]吲哚二酮的光化学方法。这种不含过渡金属和光敏剂的方案在温和的反应条件下以中等至良好的收率提供了多种二氟烷基化吡咯并[1,2- a ]吲哚二酮。最吸引人的是，该反应可以在阳光照射下顺利进行，这为二氟烷基化吡咯并[1,2- a ]吲哚二酮开辟了一条新途径。