2,2-difluoro-2-iodo-N-(4-methoxyphenyl)acetamide | 1239497-25-6

• 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-(4-methoxyphenyl)acetamide
• CAS: 1239497-25-6
• 化学式: C₉H₈F₂INO₂
• 分子量: 327.069
• InChiKey: XZXOVSBDOOFLIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-2-iodo-N-(4-methoxyphenyl)acetamide 在 铜 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以49%的产率得到2,2,3,3-tetrafluoro-N(1),N(4)-bis(4-methoxyphenyl)succinamide
  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：

  在 水 、 碳酸氢钠 、 sodium sulfite 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2,2-difluoro-2-iodo-N-(4-methoxyphenyl)acetamide
  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

文献信息

• 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。