(4-hydroxybenzylidene)bis(dimedone) | 329736-70-1

• 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: (4-hydroxybenzylidene)bis(dimedone)
• 英文别名: 4-hydroxyphenyltetraketone；5,5,5',5'-tetramethyl-2,2'-(4-hydroxy-benzylidene)-bis-cyclohexane-1,3-dione；5,5,5',5'-Tetramethyl-2,2'-(4-hydroxy-benzyliden)-bis-cyclohexan-1,3-dion；Tetraketone, 6；2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(4-hydroxyphenyl)methyl]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 329736-70-1
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: FOLUVRMDMOXLNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 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：
  88.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-hydroxybenzylidene)bis(dimedone) 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.03h， 以84%的产率得到9-(4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  二甲基二酮与芳族醛缩合合成四氢和八氢氧杂蒽衍生物

  摘要：

  DOI：

  10.1007/bf01164861
• 作为产物：
  描述：

  (Z)-N-(4-hydroxybenzylidene)aniline oxide 、 5,5-二甲基-1,3-环己二酮 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到(4-hydroxybenzylidene)bis(dimedone)
  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

• A bright entry to improve the performance of DSSCs with the influence of novel optoelectronic acridinedione based macromolecules in I−/I3− electrolytes
  作者：Govindasami Periyasami、Raju Rajesh、Natarajan Arumugam、Raghavachary Raghunathan、Shanmugam Ganesan、Pichai Maruthamuthu

  DOI：10.1039/c3ta12221b

  日期：——

  The performance of Ru(II) dye-sensitized nanocrystalline TiO2 solar cells (DSSCs) is described with newly synthesized multivalent macromolecules, containing excellent optoelectronic acridinedione linked with 1,2,3-triazole units, via a novel and convenient Cu(I)-catalyzed alkyne and azide 1,3-dipolar cycloaddition (CuAAC) reaction. These unique macromolecules have proved to be highly suitable for utilizing additives in I−/I3− redox couple electrolytes. Among the various substitutions, the maximum photo-current conversion efficiency of about 6.4% with a Voc of 810 mV was obtained with electron rich substitutions in the nitrogen heteroatom.

  新合成的多价大分子含有性能优越的吖啶二酮单元和1,2,3-三氮唑单元，通过一种新型且便捷的铜催化的炔烃和叠氮化物的1,3-偶极环加成反应（CuAAC）连接，被用于描述染料敏化纳米晶TiO2太阳能电池（DSSCs）的性能。这些独特的大分子已被证明非常适合利用在I-/I3-氧化还原电解质中的添加剂。在各种取代基中，具有富电子氮杂原子取代基的体系获得了最高的光电流转换效率约6.4%，开路电压为810 mV。
• 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
• Specific Ca²⁺Fluorescent Sensor: Signaling by Conformationally Induced PET Suppression in a Bichromophoric Acridinedione
  作者：Pichandi Ashokkumar、Vayalakkavoor T. Ramakrishnan、Perumal Ramamurthy

  DOI：10.1002/ejoc.200900570

  日期：2009.12

  the bichromophore, resulting in PET suppression in the acridinedione chromophore. Involvement of a PET process in the optical signaling was confirmed by comparing bichromophores 1a–c with non-PET compound 2 and monochromophore model compound 3. Non-PET compound 2 failed to give optical response upon Ca2+ binding as a result of the absence of a PET process in the Ca2+-bound complex. Monochromophore

  合成并表征了一系列基于吖啶二酮的双色团 podand 系统 1a-c。其中，双发色团 1c 在其他生物学上重要的金属离子（如 Na+、K+、Mg2+ 和 Zn2+）存在时显示出与 Ca2+ 的特异性结合。通过稳态发射、时间分辨发射和 1 H NMR 滴定证明了选择性络合。结合事件的信号传递是通过 Ca2+ 诱导的双生色团折叠实现的，从而导致吖啶二酮生色团中的 PET 抑制。通过将双发色团 1a-c 与非 PET 化合物 2 和单发色团模型化合物 3 进行比较，证实了 PET 过程参与光学信号。由于不存在Ca2+结合复合物中的PET过程。单发色团 3 显示出类似的光学响应，与 1c 中的相同。用 EDTA 滴定 1c 的金属离子结合络合物，从络合物中释放金属离子，从而恢复双色团的原始光物理特性。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009
• Synthesis of acridinedione derived mono spiro-pyrrolidine/pyrrolizidine derivatives—a facile approach via intermolecular [3+2] cycloaddition reaction
  作者：R. Rajesh、M. Suresh、R. Selvam、R. Raghunathan

  DOI：10.1016/j.tetlet.2014.05.133

  日期：2014.7

  A facile synthesis of acridinedione derived mono spiro-pyrrolidine and pyrrolizidine derivatives has been accomplished by 1,3-dipolar cycloaddition reaction. The O-acryloylacridinediones, as dipolarophiles reacted with azomethine ylide derived from di-/tri-ketones and sec-amino acids to give acridinedione derived mono spiropyrrolidine/pyrrolizidine derivatives in good yield.

  通过1，3-偶极环加成反应已经完成了cr啶二酮衍生的单螺-吡咯烷和吡咯并核苷衍生物的简便合成。作为双极性亲和剂的O-丙烯酰脲基吡啶二酮与衍生自二/三酮和仲氨基酸的甲亚胺基立德反应，以良好的收率得到a啶二酮衍生的单螺并吡咯烷/吡咯并吡啶衍生物。