2-(苯基氨基)环己-2-烯-1-酮 | 33670-02-9

• 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-(苯基氨基)环己-2-烯-1-酮
• 英文名称: 2-(phenylamino)cyclohex-2-enone
• 英文别名: 2-(phenylamino)-cyclohex-2-en-1-one；2-phenylamino-2-cyclohexen-1-one；2-Anilinocyclohex-2-en-1-one
• CAS: 33670-02-9
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: FHDWTVJQIRSBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(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86%的产率得到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-(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

• Multifunctionalization of Unactivated Cyclic Ketones via an Electrochemical Process: Access to Cyclic α-Enaminones
  作者：Kangfei Hu、Peng Qian、Ji-Hu Su、Zhibin Li、Jiawei Wang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.joc.8b02930

  日期：2019.2.1

  The multifunctionalization of unactivated cyclic ketones was developed via an electrochemically intermolecular α-amination under metal-free conditions. The reaction can be carried out smoothly with a broad scope of the aromatic amines substrates under mild conditions, affording a variety of α-enaminones with good to excellent yields in one step.

  通过在无金属条件下进行电化学分子间α胺化反应，开发了未活化环酮的多功能化。该反应可在温和条件下与多种芳香胺底物一起平稳进行，一步即可得到各种具有良好产率或优异产率的α-烯酮。
• 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。
• Metal-Induced Reactions of<i>O</i>-Nitroso Aldol Products
  作者：Hisashi Yamamoto、Marvin R. Morales、Norie Momiyama

  DOI：10.1055/s-2006-933123

  日期：——

  Lewis acid catalysts play an important role in the transformation of α-aminooxy ketones (O-nitroso aldol products). Three different reactions of O-nitroso aldol products promoted by metal ions are described.

  路易斯酸催化剂在δ-氨基氧基酮（O-亚硝基醛醇产物）的转化过程中发挥着重要作用。本文介绍了金属离子促进 O-亚硝基醛醇产物的三种不同反应。
• 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。
• Copper-catalyzed amination of alkenes and ketones by phenylhydroxylamine
  作者：Chi-Ming Ho、Tai-Chu Lau

  DOI：10.1039/b004286m

  日期：——

  alkenes using phenylhydroxylamine as the nitrogen fragment donor has been investigated. The best catalyst is CuCl2·2H2O, which produces moderate yields of allylamines with high regioselectivity resulting from double bond transposition. A mechanism similar to that for the molybdenum and the FePc systems is proposed. The first step in the catalytic cycle is the formation of nitrosobenzene from the oxidation

  已经研究了许多铜配合物和盐对使用苯基羟胺作为氮片段供体的烯烃的烯丙基胺化的催化活性。最好的催化剂是CuCl 2 ·2H 2 O，该催化剂可产生中等收率的烯丙胺，并由于双键易位而具有较高的区域选择性。提出了一种与钼和FePc体系相似的机理。催化循环的第一步是由苯羟胺被Cu（II）氧化形成亚硝基苯。下一步是烯烃与PhNO的烯反应生成烯丙基羟胺，然后将其通过Cu（I）还原为烯丙胺产物，从而再生Cu（II）。同一系统还可以将氮片段转移到环状酮的α-碳上。在某些情况下，这伴随着脱氢反应产生α-胺化，α，β-不饱和酮。