N-(4-chlorophenyl)-N-phenylformamide

• 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: N-(4-chlorophenyl)-N-phenylformamide
• 英文别名: N-4-chlorophenyl-N-phenylformamide
• 化学式: C₁₃H₁₀ClNO
• 分子量: 231.681
• InChiKey: WQDNSUZPLDDVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-N-苯基甲亚胺 在 sodium perborate 作用下， 以 三氟乙酸 为溶剂， 以52%的产率得到N-(4-chlorophenyl)-N-phenylformamide
  参考文献：
  名称：

  使用过硼酸钠将亚胺氧化重排为甲酰胺

  摘要：

  过硼酸钠四水合物（SPB）在三氟乙酸溶液中氧化C-芳基或烷基N-芳基亚胺6或20，得到重排的N，N-二取代甲酰胺9和21。产率是可变的，取决于溶剂，对于电子中性的C-芳基取代基或C - s-烷基取代基，可获得最佳产率（50-60％）。通过中间体oxaziridine 5使产物形成合理化，该中间体可通过酸催化的ON键断裂。这些中间体的另一种CO键裂解可导致醛的形成，而醛是常见的副产物。N-芳基取代基和不稳定的碳上正电荷的C-取代基似乎有利于重排。通过观察到苯乙醛苯基亚胺的MCPBA氧化产生重排的N，N-二苯基甲酰胺，进一步提供了对恶唑烷中间体5的支持。在SPB氧化重排的条件下，三氮过氧乙酸的初始形成很可能会发生恶唑烷的形成。醛亚胺这种新的重排1→2的立体化学方面使用进行了调查反式和独联体-myrtanal 25和30。据信使用反式myrtanal 26的N -4-甲苯基亚胺观察到的差向异

  DOI：

  10.1016/s0040-4020(97)00101-4

文献信息

• On the Oxidation of Different Iminic Bonds by Excess of 3-Chloroperbenzoic Acid
  作者：Luigino Troisi、Marina Carrozzo、Cinzia Citti、Aurelia Falcicchio、Rosmara Mansueto、Francesca Rosato、Giuseppe Cannazza

  DOI：10.1055/s-0032-1317760

  日期：——

  In the present work the behavior of different substituted iminic bonds toward the oxidative action of 3-chloroperbenzoic acid is reported. The C=N bond was or was not oxidized to oxaziridines, amides, oximes, nitroso-, nitro-, and azodioxy compounds depending on the substituents at the iminic group and on the ­imine/MCPBA stoichiometric ratio.

  在目前的工作中，报告了不同取代亚胺键对 3-氯过苯甲酸氧化作用的行为。根据亚胺基上的取代基和亚胺/MCPBA 化学计量比，C=N 键是否被氧化为氧氮丙啶、酰胺、肟、亚硝基-、硝基-和偶氮二氧基化合物。
• Direct Synthesis of <i>N,N</i>-Disubstituted Formamides by Oxidation of Imines Using an HFIP/UHP System
  作者：Natalia Llopis、Patricia Gisbert、Alejandro Baeza

  DOI：10.1021/acs.joc.0c01579

  日期：2020.9.4

  The straightforward synthesis of N,N-disubstituted formamides using a combination of 1,1,1,3,3,3-hexafluoroispropanol (HFIP) and H2O2 is described. The unique features of HFIP allowed the utilization of a green oxidant such as H2O2, and the products, arising from an oxidation–rearrangement sequence, were obtained in good to high yields under smooth reaction conditions.

  描述了使用1,1,1,3,3,3-六氟异丙醇（HFIP）和H 2 O 2的组合直接合成N，N-二取代甲酰胺。HFIP的独特功能允许利用绿色氧化剂（例如H 2 O 2），并且在平稳的反应条件下，以高至高收率获得了由氧化重排序列产生的产物。
• An oxidative rearrangement of C,N-diarylaldimines to formamides using sodium perborate
  作者：Pakawan Nongkunsarn、Christopher A. Ramsden

  DOI：10.1016/s0040-4039(00)61698-2

  日期：1993.10

  Treatment of C,N-diaryladium (5) with sodium tetrahydrate in triflouroacetic acid solution at 70–80°C results in an oxidative rearrangement to N,N-diarylformamides (6(Scheme 1). A mechanism involving the initial formation of 2,3-diaryloxaziridines is proposed (Scheme 2).

  在70-80°C的三氟乙酸溶液中用四水合钠处理C，N-二芳基dium（5）会导致N，N-二芳基甲酰胺的氧化重排（6（方案1）。一种机理最初涉及2的形成）提出了3-二芳基恶唑烷（方案2）。
• Copper-catalyzed C–N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
  作者：Dean P. Phillips、Xue-Feng Zhu、Thomas L. Lau、Xiaohui He、Kunyong Yang、Hong Liu

  DOI：10.1016/j.tetlet.2009.10.041

  日期：2009.12

  The copper-catalyzed C-N coupling of amides to arylhalides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that CsF is sufficiently basic to promote the cross-coupling of amides and carbamates With aryl halides. Most aryl iodides coupled in high yield at room temperature. This alternative base may be a suitable replacement for substrates that are incompatible with high temperature and strongly basic conditions and can further enhance the chemoselectivity of this reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• Oxidation of aldimines to amides by m-CPBA and BF3·OEt2
  作者：Gwang-il An、Misoo Kim、Jin Yeon Kim、Hakjune Rhee

  DOI：10.1016/s0040-4039(03)00156-4

  日期：2003.3

  Several amides were obtained in high yields by an efficient method from the corresponding imines which are readily prepared from aldehydes. This procedure involves the oxidation of aldimines with m-CPBA and BF3.OEt2. In this reaction, the product is strongly influenced by the electron releasing capacity of the aromatic substituent. (C) 2003 Elsevier Science Ltd. All rights reserved.