3-(1,3-dioxo-1,3-diphenylpropan-2-yl)cyclohexanone | 906006-36-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-(1,3-dioxo-1,3-diphenylpropan-2-yl)cyclohexanone
• 英文别名: 2-(3-oxocyclohexyl)-1,3-diphenylpropane-1,3-dione；2-(3-oxocyclohexyl)-1,3-diphenylpropan-1,3-dione
• CAS: 906006-36-8
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: IPNIHZSFVNLPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 二苯甲酰基甲烷 在 4-(dimethylamino)pyridinium acetate 作用下， 反应 2.0h， 以75%的产率得到3-(1,3-dioxo-1,3-diphenylpropan-2-yl)cyclohexanone
  参考文献：
  名称：

  Amberlyst-15催化将β-二羰基化合物的迈克尔加成至烯酮和意想不到的闭环产物中

  摘要：

  使用Amberlyst-15或Amberlyst-15-DMAP乙酸盐体系作为催化剂，研究了2,4-戊二酮，二苯甲酰甲烷和乙酰乙酸乙酯与烯酮的共轭加成反应。当在Amberlyst-15存在下进行2，4-戊二酮反应时，取决于反应条件，获得了缀合物加成和/或缀合物加成引发的闭环产物。然而，与2，4-戊二酮不同，二苯甲酰甲烷仅产生与Amberlyst-15的共轭加成产物。当使用Amberlyst-15-DMAP乙酸酯体系时，始终仅与β-二羰基化合物获得共轭加成产物，而与反应条件无关。

  DOI：

  10.1016/j.tet.2017.05.092

文献信息

• Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones
  作者：Sunil V. Pansare、Rajinikanth Lingampally

  DOI：10.1039/b812038b

  日期：——

  Guanidinyl pyrrolidines derived from ‘S’-proline are effective catalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cyclohexenone and cyclopentenone in the absence of basic additives. The stereoselectivity is strongly dependant on catalyst loading as well as reaction concentration.

  衍生自“ S ”-脯氨酸的胍基吡咯烷是将丙二酸酯，硝基烷和其他碳原子和杂原子亲核试剂对映选择性共轭加成的有效催化剂。环己烯酮 和 环戊烯酮在没有碱性添加剂的情况下。立体选择性很大程度上取决于催化剂的负载以及反应浓度。
• Solvent-free Michael addition of 2-cyclohexenone under ultrasonic irradiation in the presence of long chain dicationic ammonium salts
  作者：AYTEK ÖGE、MURAT EMRAH MAVİŞ、ÇİĞDEM YOLAÇAN、FERAY AYDOĞAN

  DOI：10.3906/kim-1104-63

  日期：——

  Long chain dicationic ammonium salts (1a-1c), easily prepared from tert-amines and dihaloalkanes, were successfully used as efficient phase-transfer catalysts in the Michael addition reaction of various active methylene compounds to 2-cyclohexenone without solvent under ultrasonic irradiation. The investigated dicationic salts were more effective than monocationic tetrabutylammonium bromide, with short reaction times and high yields. This methodology was established under phase-transfer catalytic conditions and ultrasonic effects with many advantages, including the easy and cost-effective synthesis of the catalyst, mild reaction conditions, short reaction times, good yields, simple work-up procedures, and environmental friendliness.

  长链双阳离子季铵盐（1a-1c），通过叔胺和二卤代烷的简易制备，成功地作为高效相转移催化剂应用于超声辐射下无溶剂的各类活性亚甲基化合物与2-环己烯酮的迈克尔加成反应中。研究的双阳离子盐比单阳离子四丁基溴化铵更为有效，具有短反应时间和高产率的特点。该方法在相转移催化条件和超声效应下建立，具有许多优点，包括催化剂的简易和成本效益高的合成、温和的反应条件、短反应时间、良好的产率、简化的后处理过程以及环境友好性。
• Ionic Liquids Made with Dimethyl Carbonate: Solvents as well as Boosted Basic Catalysts for the Michael Reaction
  作者：Massimo Fabris、Vittorio Lucchini、Marco Noè、Alvise Perosa、Maurizio Selva

  DOI：10.1002/chem.200901891

  日期：2009.11.16

  introduces neat NMR spectroscopy of the ionic liquids as a probe for solute–solvent interactions as well as a tool for characterisation. Our studies show that high catalytic efficacy of functional ionic liquids can be achieved by integrating their green synthesis, along with a fine‐tuning of their structure. Demonstrating that ionic liquid solvents can be made by a truly green procedure, and that their properties

  本文介绍了1）绿色合成一类甲基铵和甲基phosph离子液体（IL）的方法，2）如何通过阴离子交换来调节其酸碱性质，3）这些材料的完整的NMR光谱表征4）它们作为碱促进的碳-碳键形成反应的活性有机催化剂的应用。叔胺或膦与碳酸二甲酯的甲基化会导致形成无卤甲基碳酸甲酯盐，这些盐可以很容易地进行阴离子交换，生成一系列具有不同熔点，溶解度，酸碱性质的衍生物，稳定性和粘度。特别是用水处理，会产生碳酸氢盐交换的液态鎓盐。这些被证明具有很强的碱性，足以有效地催化迈克尔反应。实验表明，在这些系统中，相对于无机碳酸氢盐，碳酸氢盐的碱度提高了两个数量级。这些以催化量使用的碱性离子液体甚至比传统的强有机碱更好。本工作还介绍了离子液体的纯NMR光谱，作为溶质-溶剂相互作用的探针以及表征的工具。我们的研究表明，通过整合功能性离子液体的绿色合成以及对其结构进行微调，可以实现高催化效率。证明可以通过真正的绿色程序来制备离
• Heterobimetallic Pd–Sn Catalysis: Michael Addition Reaction with C-, N-, O-, and S-Nucleophiles and in Situ Diagnostics
  作者：Debjit Das、Sanjay Pratihar、Sujit Roy

  DOI：10.1021/jo302643v

  日期：2013.3.15

  An efficient Michael addition reaction of differently substituted enones with carbon, sulfur, oxygen, and nitrogen nucleophiles has been achieved by a new heterobimetallic "Pd-Sn" catalyst system. The nature of the catalytically relevant species and their interactions with the enone moiety has been examined by spectroscopy. The effect of ligand and the coordination mode of enone with "Pd-Sn" heterobimetallic system have been investigated by kinetics and DFT studies. A straightforward application of this methodology is shown in the synthesis of 1,4-oxathiepane core.