2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione | 329734-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione
• 英文别名: 2,2'-[(4-nitrophenyl)methylene]-bis-[5,5-dimethyl-1,3-cyclohexanedione]；2,2'-(4''-nitrophenyl)methylene-bis(5,5-dimethylcyclohexane-1,3-dione)；2,2'-(4-nitrobenzylidene)-bis(5,5'dimethylcyclohexane-1,3-dione)；2,2'-(4-nitrobenzylidene)bis(5,5-dimethylcyclohexane-1,3-dione)；2,2'-(4-nitrobenzylidene)bisdimedone；5,5,5',5'-tetramethyl-2,2'-(4-nitro-benzylidene)-bis-cyclohexane-1,3-dione
• CAS: 329734-82-9
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: AKAPCQRQGHJPED-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  600.2±55.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione 在 溶剂黄146 、 calcium chloride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 9-(4-aminophenyl)-3,3,6,6,10-pentamethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
  参考文献：
  名称：

  A Novel Colorimetric and Fluorescent Chemosensor for Anions Involving PET and ICT Pathways

  摘要：

  A novel colorimetric and fluorescent chemosensor ADDTU-1 bearing dual receptor sites, which shows specific optical signaling for AcO-, H2PO4-, and F- over other anions and dual response toward AcO- and F- via PET and ICT mechanisms, is described.

  DOI：

  10.1021/ol047463k
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 N-(4-nitrobenzylidene)aniline oxide 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-nitrophenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione
  参考文献：
  名称：

  Aldonitrones as Aldehyde Equivalents: An Efficient, Green, and Novel Protocol for the Synthesis of 1,8-Dioxo-octahydroxanthenes

  摘要：

  A novel, self-catalyzed, solvent-free, microwave-enhanced, green, and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones by condensing aldo-nitrones (imine oxide) and dimedone (5,5-dimethyl-1,3-cyclohexanedione) under microwave irradiation is disclosed. Product formation (viz. xanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones) is dependent on reaction conditions. The entire process is green and sustainable in terms of solvents, chemicals, reaction procedure, and yields. A plausible reaction mechanism of this reaction is also proposed. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.

  DOI：

  10.1080/00397911.2012.736584

文献信息

• Merging supramolecular catalysis and aminocatalysis: amino-appended β-cyclodextrins (ACDs) as efficient and recyclable supramolecular catalysts for the synthesis of tetraketones
  作者：Yufeng Ren、Bo Yang、Xiali Liao

  DOI：10.1039/c6ra01002d

  日期：——

  β-CD were synthesized and employed in the catalytic synthesis of a series of tetraketones as supramolecular catalysts in water for the first time. Yields of 58–97% were obtained with up to 30 examples of substrate. The catalyst could be recycled easily, while a 92% yield and 84% rate of catalyst recovery could be achieved after 8 cycles of catalyst recycling. Moreover, a catalytic mechanism merging

  合成了设计良好的，在β-CD的主面上具有不同长度的氨基侧链的氨基附加β-环糊精（ACD），并将其首次用于一系列四酮的催化合成，作为水中的超分子催化剂。使用多达30个底物实例可获得58-97％的产率。该催化剂可以容易地再循环，而在8次催化剂再循环之后，可以达到92％的收率和84％的催化剂回收率。此外，通过详细的1D和2D NMR，ESI-MS和Job图分析，可以提出将超分子催化和氨基催化相结合的催化机理。该协议保留了环境温度，绿色介质，操作简单，基材范围广，产率高，
• Application of $$\hbox {SiO}_{{2}}$$ SiO 2 nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones
  作者：Heshmatollah Alinezhad、Armin Ahmadi、Parvin Hajiabbasi

  DOI：10.1007/s12039-019-1607-8

  日期：2019.4

  SiO}_2}}\) nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using \(\hbox SiO}_2}}\)

  摘要在本文中，我们探讨了\（\ hbox SiO} _ 2}} \）纳米颗粒（NPs）在合成2,3-二氢-1中作为一种环保，高效且可重复使用的催化剂的催化活性。H -perimidines以及四酮。对于四酮合成，通过迈克尔加成反应，通过苯甲醛与5,5-二甲基-1,3-环己二酮在无溶剂条件下使用\（\ hbox SiO} _ 2} } \） NPs是一种有效的固体催化剂。此外，对于2,3-二氢-1 H-亚氨基吡啶的合成，使用\（\ hbox SiO} _ 2}} \）在无溶剂的条件下可以实现各种醛与1,8-二氨基萘的环缩合。NP在室温下作为催化剂。结果表明，两种合成方法均具有催化作用。在这项工作中，合成了4-（2,3-二氢-1 H-嘧啶-2-基）苄腈和2-（吡啶-4-基）-2,3-二氢-1 H-嘧啶作为新化合物。另外，对\（\ hbox SiO} _ 2}} \） N
• KNOEVENAGEL CONDENSATION OF ALDEHYDES WITH CYCLIC ACTIVE METHYLENE COMPOUNDS IN WATER
  作者：Zhongjiao Ren、Weiguo Cao、Weiqi Tong、Xiuping Jing

  DOI：10.1081/scc-120004844

  日期：2002.1

  ABSTRACT A new route of Knoevenagel condensation of aromatic aldehydes with Meldrum's acid, barbituric acid and dimedone in the presence of cetyltrimethyl ammonium bromide at room temperature in water is described.

  摘要 描述了在室温下，在十六烷基三甲基溴化铵存在下，芳香醛与 Meldrum 酸、巴比妥酸和二甲酮在水中进行 Knoevenagel 缩合的新路线。
• A Green and Highly Efficient Protocol for Catalyst-free Knoevenagel Condensation and Michael Addition of Aromatic Aldehydes with 1,3-Cyclic Diketones in PEG-400
  作者：Nemati Firouzeh、Kiani Hossein

  DOI：10.1002/cjoc.201100005

  日期：2011.11

  A convenient, highly efficient and green approach for synthesis of tetraketones from aromatic aldehydes with dimedone and 1,3‐indanedione at room temperature in PEG‐400 is described. The use of PEG‐400 as the reaction medium and avoiding the use of any catalyst makes the process environmentally benign. Seven new compounds are reported.

  描述了一种在室温下PEG-400中由芳族醛与二甲酮和1,3-茚满二酮合成四酮的便捷，高效且绿色的方法。使用PEG-400作为反应介质并避免使用任何催化剂会使该过程对环境无害。据报道有七种新化合物。
• A novel approach towards the synthesis of tricyclic systems based on pyridine, pyran, thiopyran, azepine, oxepin, thiepin, and pyrimidine rings under different solvent conditions
  作者：Anand Sachar、Poonam Gupta、Shallu Gupta、R. L. Sharma

  DOI：10.1139/v10-015

  日期：2010.5

  Synthesis of some oxygen, nitrogen, and sulfur based condensed heterocycles by the condensation of dimedone with aromatic monoaldehyde under different solvent conditions has been achieved.

  在不同溶剂条件下，通过二聚酮与芳香族一醛的缩合，合成了一些氧、氮和硫基缩合杂环。