3-(piperidin-1-yl)cyclohex-2-en-1-one | 16179-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(piperidin-1-yl)cyclohex-2-en-1-one
• 英文别名: 3-(piperidin-1-yl)cyclohex-2-enone；3-Piperidino-cyclohex-2-enon；3-piperidin-1-ylcyclohex-2-en-1-one
• CAS: 16179-65-0
• 化学式: C₁₁H₁₇NO
• mdl: MFCD24389885
• 分子量: 179.262
• InChiKey: ZRBBCNYLYIKUNK-UHFFFAOYSA-N

物化性质

• 沸点：
  166-167 °C(Press: 1 Torr)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(piperidin-1-yl)cyclohex-2-en-1-one 在 benzyltrimethylammonium iododichloride 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 3-哌啶基苯酚
  参考文献：
  名称：

  由环己烷-1,3-二酮形成3-氨基酚

  摘要：

  在室温下，MeCN中DBU对3-氨基-2-氯环己-2--2-烯-1-酮的作用形成间位氨基酚。用易制备的卤化剂BnNMe 3 ·ICl 2在MeOH-CH 2 Cl 2中处理3-氨基环己-2-烯-1-酮可生成氯化合物。氨基必须带有两个取代基：两个芳基，一个芳基和一个烷基或两个烷基。这种类型的3-氨基环己-2-烯-1-酮很容易由环​​己-2-烯-1-酮和伯或仲胺制得。

  DOI：

  10.1021/acs.joc.0c02284
• 作为产物：
  描述：

  1,3-环己二酮 在 哌啶 作用下， 以 甲苯 为溶剂， 以84%的产率得到3-(piperidin-1-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Rigidified merocyanine dyes with different aspect ratios: Dichroism and photostability

  摘要：

  A series of new rigidified merocyanines were investigated with regard to their optical properties as dichroic dyes. Guest/host-mixtures of the dyes were prepared using a liquid crystal and a reactive mesogen mixture. Their dichroism was studied using linearly-polarized UV/Vis-spectroscopy. A strong dependence of the dichroic ratio on the aspect ratio, the number of double bonds in the molecular structure, and on the maximum wavelength of absorption was found. A strategy to increase the aspect ratio has also been demonstrated. Additionally, the photostability was characterized using continued irradiation with polychromatic light from a xenon source. High photostability was found in all host mixtures in the absence of oxygen by alignment in a matrix. The suitability for their application as dichroic dyes in thin layer polarizers and guest/host-displays is herein discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.04.041

文献信息

• An efficient method for <i>retro</i>-Claisen-type C–C bond cleavage of diketones with tropylium catalyst
  作者：M. A. Hussein、V. T. Huynh、R. Hommelsheim、R. M. Koenigs、T. V. Nguyen

  DOI：10.1039/c8cc07329e

  日期：——

  cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Brønsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of

  的复古-Claisen反应是在有机合成常用来访问酯衍生物由1,3-二羰基前体。通常通过许多过渡金属路易斯酸催化剂或有机布朗斯台德酸/碱来促进该反应中的C–C键裂解。在本文中，我们报告了一种新的便捷有效的方法，该方法利用对苯二酸铵离子作为温和且环保的有机催化剂来介导逆克莱森型反应。使用这种方法，可以通过1，3-二羰基化合物的溶剂分解获得一系列有价值的合成物质。
• Intermolecular Multiple Dehydrogenative Cross‐Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
  作者：Tianzhang Wang、Guowei Chen、Yu‐Jing Lu、Qian Chen、Yanping Huo、Xianwei Li

  DOI：10.1002/adsc.201900419

  日期：2019.8.21

  versatile oxidative coupling reaction was developed for the synthesis of valuable β‐functionalized unsaturated ketones and meta‐substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well‐established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic

  开发了一种有效且通用的氧化偶联反应，用于合成有价值的β-官能化不饱和酮和间位取代的苯酚。在分子内反应的情况下，通过多次脱氢偶联实现快速的分子复杂性已经是一种行之有效的策略。在这里，我们报告了使用廉价的氧化铜（I）作为催化剂，酮与亲核胺或硼酸之间的分子间多重脱氢偶联。该方法可轻松获得高度理想的化学产品，例如α，β-不饱和酮，烯胺酮和合成相关的间位取代的苯酚。
• Synthesis, spectral and structural characterization of cobalt(III) dithiocarbamato complexes: Catalytic application for the solvent free enamination reaction
  作者：Pooja Bharati、A. Bharti、P. Nath、M.K. Bharty、R.J. Butcher、N.K. Singh

  DOI：10.1016/j.poly.2015.10.007

  日期：2015.12

  using 1–2 mol% of the above cobalt(III) complexes as catalysts and these have been characterized by NMR, GC–MS and X-ray crystallography. Complexes 1, 2 and 3 are stabilized by intermolecular C–H⋯S interactions, leading to the formation of supramolecular architectures. Thermogravimetric analysis of complexes 1 and 2 have been investigated by TG-DTA, which indicate that cobalt sulfide is formed as the

  一些新的钴（III）配合物[Co（mpcdt）3 ]（1），[Co（ppcdt）3 ]（2）和[Co（mppcdt）3 ]·0.25CHCl的合成，光谱，结构和催化性能参照图3（3），已经描述了衍生自4-甲基哌嗪-1-碳二硫酸酯（mpcdt），4-苯基哌嗪-1-碳二硫酸酯（ppcdt）和4-（2-甲氧基苯基）哌嗪-1-碳二硫代酸酯（mppcdt）。使用1–2 mol％的上述钴（III）配合物，通过β-酮酸酯和1,3-二酮与脂肪族和芳香族胺的反应，可以得到约90％的产率的一系列β-烯胺酯和β-烯酮。催化剂，并已通过NMR，GC-MS和X射线晶体学进行了表征。复合体1，2和3是通过分子间C-H⋯小号相互作用来稳定，导致超分子结构的形成。通过TG-DTA研究了配合物1和2的热重分析，结果表明形成了硫化钴作为最终产物。
• Influence of Chromophore Length and Acceptor Groups on the Optical Properties of Rigidified Merocyanine Dyes
  作者：Katharina Christina Kreß、Thomas Fischer、Joachim Stumpe、Wolfgang Frey、Melanie Raith、Omid Beiraghi、S. Holger Eichhorn、Stefan Tussetschläger、Sabine Laschat

  DOI：10.1002/cplu.201300308

  日期：2014.2

  series of rigidified tri-, penta- and heptamethine merocyanine dyes were synthesised. A piperidyl moiety was chosen as the electron-donating substituent while the electron-accepting group was varied from ketones to malononitriles and cyanoacetates. The structures of the compounds in the solid state and in solution were elucidated by X-ray diffraction and NMR spectroscopy, respectively, while optical properties

  合成了三组刚性的三，五和七甲亚甲基花青染料。选择哌啶基部分作为供电子取代基，同时使电子接受基团从酮到丙二腈和氰基乙酸酯变化。分别通过X射线衍射和NMR光谱阐明了固态和溶液中化合物的结构，同时通过吸收和发射光谱研究了光学性质。作为一般趋势，基于对丙二腈>氰基乙酸酯>酮的溶剂溶变色行为的分析，其受体性能下降。在B3LYP 6-311 + G（d）的理论水平上的计算进一步支持了实验结果。
• Fe-Catalyzed enaminone synthesis from ketones and amines
  作者：Wenfeng Wu、Zhuxian Wang、Qun Shen、Qiang Liu、Huoji Chen

  DOI：10.1039/c9ob01137d

  日期：——

  We have developed an iron-catalyzed direct olefination for enaminone synthesis, with saturated ketones as a source of olefins. This direct ketone β-functionalization reaction has readily available starting materials and a wide range of substrates and requires mild reaction conditions.

  我们已经开发出铁催化的直接烯化反应，用于烯胺酮合成，其中饱和酮是烯烃的来源。该直接的酮β-官能化反应具有容易获得的起始原料和多种底物，并且需要温和的反应条件。

表征谱图