2-((4-氯苯基)氨基)环己-2-烯-1-酮 | 53475-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-((4-氯苯基)氨基)环己-2-烯-1-酮
• 英文名称: 2-((4-chlorophenyl)amino)cyclohex-2-en-1-one
• 英文别名: 2-(4-chlorophenylamino)cyclohex-2-enone
• CAS: 53475-33-5
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: HPGQCEBPHRUGMD-UHFFFAOYSA-N

物化性质

• 沸点：
  379.6±42.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((4-氯苯基)氨基)环己-2-烯-1-酮 在 乙酸酐 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 0.17h， 以67%的产率得到6-氯-2,3,4,9-四氢-1H-咔唑-1-酮
  参考文献：
  名称：

  Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C–C bond formation

  摘要：

  A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2-enone with hypervalent iodine reagent PhI(OCOCF3)2 (FIFA), through a direct intramolecular oxidative C(sp(2))-C(sp(2)) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]lindol-6(5H)-one skeletons. The mechanism of the process was proposed and briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.083
• 作为产物：
  描述：

  2-氯环己酮 生成 2-((4-氯苯基)氨基)环己-2-烯-1-酮
  参考文献：
  名称：

  General method for the synthesis of indoles

  摘要：

  DOI：

  10.1021/ja00824a028

文献信息

• Synthesis of α-enaminones from cyclic ketones and anilines using oxoammonium salt as an oxygen transfer reagent
  作者：Biping Xu、Yaping Shang、Xiaoming Jie、Xiaofeng Zhang、Jian Kan、Subhash Laxman Yedage、Weiping Su

  DOI：10.1039/c9gc03845k

  日期：——

  A convenient and straightforward transformation of cyclic ketones with anilines at room temperature has been developed using oxoammonium salt TEMPO+PF6− as an oxidant. This method enabled the synthesis of a broad range of α-enaminones. The 18O-labeling experiment demonstrated that oxoammonium salt served as the oxygen transfer reagent.

  与苯胺在室温下的环酮的方便和简单的改造已经使用氧代铵盐TEMPO开发+ PF 6 -作为氧化剂。该方法能够合成多种α-烯胺。的18 O型标记实验表明，氧代铵盐担任氧转移试剂。
• Acid/Base-Co-catalyzed Direct Oxidative α-Amination of Cyclic Ketones: Using Molecular Oxygen as the Oxidant
  作者：Yi-Jin Li、Lu Zhang、Na Yan、Xiang-He Meng、Yu-Long Zhao

  DOI：10.1002/adsc.201701103

  日期：2018.2.1

  novel acid/base‐co‐catalyzed direct intermolecular α‐amination of various cyclic ketones has been developed for the first time. The reaction employs molecular oxygen as the sole oxidant under metal‐free conditions. The reaction tolerates a wide range of various anilines, especially primary diamine derivatives, and provides a simple and efficient method for the constructions of α‐amino enones and benzodiazepine

  首次开发了一种新颖的酸/碱催化的各种环酮的直接分子间α-胺化反应。该反应在无金属条件下使用分子氧作为唯一的氧化剂。该反应可耐受各种苯胺，尤其是伯二胺衍生物，并为一步构建α-氨基烯酮和苯并二氮杂卓衍生物提供了一种简单有效的方法。
• Can Primary Arylamines Form Enamine? Evidence, α-Enaminone, and [3+3] Cycloaddition Reaction
  作者：E. H. Nisala Fernando、Jose Cortes Vazquez、Jacqkis Davis、Weiwei Luo、Vladimir N. Nesterov、Hong Wang

  DOI：10.1021/acs.joc.1c01462

  日期：2021.11.5

  α-enaminone formation suggests that an amine radical cation generated through O2 singlet energy transfer was involved in initiating α-enaminone formation. The reactivity and utility of α-enaminones were explored with a [3+3] cycloaddition reaction of enones affording dihydropyridines in good yields (58–85%). α-Enaminones displayed a set of reactivities that is different from that of enamines. The knowledge

  通过核磁共振光谱检测并证实了由伯芳基胺形成烯胺。发现自由基猝灭剂例如(2,2,6,6-四甲基哌啶-1-基)氧化基的存在对于检测烯胺形成是必不可少的。还开发了由伯芳基胺和酮直接合成 α-烯胺酮的方法。α-烯胺酮形成的机理研究表明，通过 O 2产生的胺自由基阳离子单线态能量转移参与了α-烯胺酮的形成。通过烯酮的 [3+3] 环加成反应探索了 α-烯胺酮的反应性和效用，以良好的产率 (58-85%) 提供二氢吡啶。α-烯胺酮表现出一组不同于烯胺的反应性。在这项工作中获得的知识提高了我们对有机化学的基本理解，为烯胺催化提供了见解和新机会。
• Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves
  作者：Weiwei Luo、Zhicheng Sun、E. H. Nisala Fernando、Vladimir N. Nesterov、Thomas R. Cundari、Hong Wang

  DOI：10.1039/d0sc02078h

  日期：——

  α-enaminones with quinones through facile manipulation of catalyst and additive, leading to structurally completely different products. The two divergent processes, which involve formal aza- and oxo-[3 + 2] cycloaddition reactions, are mediated by chiral phosphoric acid and molecular sieves, respectively. While inclusion of phosphoric acid in the reaction switched the reaction pathway to favor the

  通过催化剂和添加剂的简便操作，已开发出一种双发散方法，用于α-烯胺酮与醌的反应，从而得到结构上完全不同的产物。涉及正式氮杂和氧代-[3 + 2]环加成反应的两个发散过程分别由手性磷酸和分子筛介导。虽然在反应中加入磷酸会改变反应路径，从而有利于有效形成多种氮取代的吲哚，向反应中添加4Å分子筛，再次切换了反应路径，从而导致2,3-二氢苯并呋喃的对映选择性合成，在温和条件下具有优异的收率和对映选择性。这项工作的研究表明，手性磷酸的作用是降低过渡态能量，并促进形成正式氮杂-[3 + 2]环加成反应的酰胺中间体，而分子筛有助于促进质子向氧代[3+]的转移。 2]环加成。在这项工作中还公开了α-烯胺酮的反应性。