3,3,6,6-tetramethyl-9-(pyridin-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 359899-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,6,6-tetramethyl-9-(pyridin-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-4-yl)-2H-xanthene-1,8(5H,9H)-dione；3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；3,3,6,6-tetramethyl-9-pyridin-4-yl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 359899-42-6
• 化学式: C₂₂H₂₅NO₃
• mdl: MFCD00160412
• 分子量: 351.445
• InChiKey: YBJMHOJAYIXUET-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  514.0±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3,6,6-tetramethyl-9-(pyridin-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 、 肼 在 zinc ferrite 作用下， 以 水 为溶剂， 反应 3.0h， 以90%的产率得到N-amino-9-(pyridin-4-yl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)dione
  参考文献：
  名称：

  Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester

  摘要：

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。

  DOI：

  10.1039/c3gc42095g
• 作为产物：
  描述：

  4-吡啶甲醛 、 5,5-二甲基-1,3-环己二酮 在 zinc ferrite 作用下， 以 水 为溶剂， 反应 3.0h， 以92%的产率得到3,3,6,6-tetramethyl-9-(pyridin-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester

  摘要：

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。

  DOI：

  10.1039/c3gc42095g

文献信息

• A Self-Assembled Trigonal Prismatic Molecular Vessel for Catalytic Dehydration Reactions in Water
  作者：Paramita Das、Atul Kumar、Prodip Howlader、Partha Sarathi Mukherjee

  DOI：10.1002/chem.201702263

  日期：2017.9.12

  A water‐soluble Pd6 trigonal prism (A) was synthesized by two‐component coordination‐driven self‐assembly of a PdII 90° acceptor with a tetraimidazole donor. The walls of the prism are constructed by three conjugated aromatic building blocks, which means that the confined pocket of the prism is hydrophobic. In addition to the hydrophobic cavity, large product egress windows make A an ideal molecular

  通过Pd II 90°受体与四咪唑供体的两组分配位驱动自组装合成了水溶性Pd 6三角棱镜（A）。棱镜的壁由三个共轭芳族结构块构成，这意味着棱镜的受限腔是疏水的。除了疏水腔外，大的产品出口窗口还使A一个理想的分子容器，可以在水性介质中的有限纳米空间中催化其他挑战性的假多组分脱水反应。这项研究是通过使用超分子分子容器微调反应条件来选择性生成中间四酮和黄嘌呤的尝试。而且，在相似的反应条件下，在不存在A的情况下，脱水产物的收率差或无收率，都支持了桶的密闭空间在水中促进这种反应的能力。此外，我们专注于锚定在Pd II配位结构中的基于四苯基乙烯的四咪唑单元的刚性化；在有水的情况下使依赖于阴离子的聚集诱导的发射成为可能。
• A New Access to 1,8-Dioxooctahydroxanthenes Using Yttrium(III) Nitrate Hexahydrate and Tin(II) Chloride Dihydrate as Effective and Reusable Catalysts
  作者：B. Karami、K. Eskandari、Z. Zare、S. Gholipour

  DOI：10.1007/s10593-014-1423-5

  日期：2014.3

  environmentally adapted synthesis of xanthene derivatives by condensation of a wide range of aryl aldehydes and cyclohexane-1,3-diones in the presence of catalytic amounts of yttrium(III) nitrate hexahydrate and tin(II) chloride dihydrate is demonstrated.

  在催化量的硝酸钇（III）六水合物和氯化锡（II）二水合物存在下，通过广泛的芳基醛和环己烷-1,3-二酮的缩合，可以高效，环保地合成x吨衍生物。
• Calcined oyster shell nanoparticles (COS NPs): a new, efficient and reusable catalyst for one-pot rapid preparation of 1,8-dioxo-octahydroxanthenes under solvent-free conditions
  作者：Narges Mohammadian、Batool Akhlaghinia

  DOI：10.1007/s11164-017-3153-7

  日期：2018.2

  Calcined oyster shell nanoparticles (COS NPs) as a novel heterogeneous nanocatalyst were prepared and fully characterized by X-ray fluorescence analysis, Fourier transform infrared spectroscopy, X-ray powder diffraction, scanning electron microscopy equipped with an energy dispersive spectrometry (SEM-EDS) and transmission electron microscopy. The composition of this catalyst was determined, and it was clearly found that the particle size of COS NPs was about 100–120 nm. The nano-structured solid catalyst as an efficient and eco-friendly catalyst was used for the synthesis of 1,8-dioxo-octahydroxanthenes via the one-pot condensation reaction of 5,5-dimethylcyclohexane-1,3-dione (dimedone) with various aldehydes under solvent-free conditions. This new methodology is cost-effective and offers several advantages such as high yield, excellent purity, short reaction time, high atom economy, simple operation and a convenient workup procedure without the use of any injurious solvents. Moreover, the catalyst can be readily reusable, and considerable catalytic activity could be achieved after the six runs.

  煅烧牡蛎壳纳米颗粒（COS NPs）作为一种新型的异相纳米催化剂被制备并进行了全面表征，包括X射线荧光分析、傅里叶变换红外光谱、X射线粉末衍射、配备能量色散光谱的扫描电子显微镜（SEM-EDS）和透射电子显微镜。确定了该催化剂的成分，并清晰地发现COS NPs的粒径约为100–120纳米。该纳米结构的固体催化剂作为一种高效且环保的催化剂，被用于通过无溶剂条件下5,5-二甲基环己烯-1,3-二酮（dimedone）与各种醛的一锅缩合反应合成1,8-二氧代-八羟蒽烯。这种新方法具有成本效益，且提供了多种优势，如高产率、优良纯度、短反应时间、高原子经济性、操作简单以及便捷的后处理程序，无需使用任何有害溶剂。此外，该催化剂可以方便地重复使用，并且经过六次反应后仍能实现显著的催化活性。
• Novel CuFe₂ O₄ @SiO₂ -OP₂ O₅ H magnetic nanoparticles: Preparation, characterization and first catalytic application to the synthesis of 1,8-dioxo-octahydroxanthenes
  作者：Farzaneh Tajfirooz、Abolghasem Davoodnia、Mehdi Pordel、Mahmoud Ebrahimi、Amir Khojastehnezhad

  DOI：10.1002/aoc.3930

  日期：2018.1

  nanoparticles and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy‐dispersive X‐ray analysis, inductively coupled plasma optical emission spectrometry and vibrating sample magnetometry. The catalytic activity of CuFe2O4@SiO2‐OP2O5H as a novel catalyst was evaluated in the synthesis of 1,8‐dioxo‐octahydroxanthenes under solvent‐free conditions. The results showed

  通过将五氧化二磷接枝到CuFe 2 O 4 @SiO 2纳米颗粒上，制备了新的功能化磁性核壳纳米颗粒CuFe 2 O 4 @SiO 2 -OP 2 O 5 H，并使用傅里叶变换红外光谱，扫描电子显微镜，能量色散X射线分析，电感耦合等离子体发射光谱和振动样品磁强法。CuFe 2 O 4 @SiO 2 -OP 2 O 5的催化活性在无溶剂条件下合成1,8-二氧代八氢氧杂蒽中评估了H作为一种新型催化剂。结果表明该催化剂具有高活性，并且在短反应时间内以高收率获得了所需产物。使用磁倾析法可以容易地回收催化剂，并且可以使用至少四次而不会明显降低催化活性。
• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。