2,2'-(1,4-phenylene-bis((2-hydroxy-4,4-dimethyl-6-oxocyclohexyl)methylene))-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)

• 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: 2,2'-(1,4-phenylene-bis((2-hydroxy-4,4-dimethyl-6-oxocyclohexyl)methylene))-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
• 英文别名: 2,2',2'',2'''-(1,4-phenylenebis(methanetriyl))tetrakis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)；2,2',2'',2'''-(1,4-phenylenebis(methanetriyl))tetrakis(3-hydroxy-5,5-dimethylcyclohex-2-enone)；2-[[4-[Bis(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)methyl]phenyl]-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
• 化学式: C₄₀H₅₀O₈
• 分子量: 658.832
• InChiKey: VGPGWPYGDJMHMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'-(1,4-phenylene-bis((2-hydroxy-4,4-dimethyl-6-oxocyclohexyl)methylene))-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3,4,6,7-tetrahydro-9-(4-(2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-1H-xanthen-9-yl)phenyl)-3,3,6,6-tetramethyl-2H-xanthene-1,8(5H,9H)-dione
  参考文献：
  名称：

  NMR spectral studies of dimedone-aldehyde adducts Part 2. 1H and 13C NMR studies of the adducts

  摘要：

  A detailed study of the 270 MHz H-1 and 67 MHz C-13 NMR spectra of four series of dimedone adducts and ''anhydrides'' is presented. A valuable (5)J(HH) homoallylic coupling has been identified which has facilitated signal locations utilising 2D HETCOR and COLOC experiments. Some earlier spectral assignments are revised.

  DOI：

  10.1016/0584-8539(96)01696-0
• 作为产物：
  描述：

  对苯二甲醛 、 5,5-二甲基-1,3-环己二酮 在 sulfuric acid-modified polyethyleneglycol-6000 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以99%的产率得到2,2'-(1,4-phenylene-bis((2-hydroxy-4,4-dimethyl-6-oxocyclohexyl)methylene))-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
  参考文献：
  名称：

  硫酸改性的PEG-6000（PEG-OSO 3 H）：一种可生物降解，可重复使用的固体酸催化剂，可在无溶剂条件下高效高效地合成新型双-Knoevenagel产品

  摘要：

  硫酸改性的PEG-6000（PEG-OSO 3 H）被用作高效，可生物降解和可重复使用的酸催化剂，用于在无热溶剂的条件下合成新型无环和杂环双-Knoevenagel产品。这种绿色的新方法的显着特点是高转化率，更清洁的反应曲线，简单的实验和后处理程序以及经济可行性。首次通过SEM-EDX和粉末XRD对催化剂进行了表征。催化剂可以重复使用几次，而不会显着降低其催化活性。

  DOI：

  10.1016/j.tetlet.2013.05.012

文献信息

• Clean Synthesis of Compounds Containing Two 4<i>H</i>‐Pyrans or Two Tetraketones in Aqueous Media
  作者：Tong‐Shou Jin、Li‐Bin Liu、Ying Zhao、Tong‐Shuang Li

  DOI：10.1080/00397910500187779

  日期：2005.9.1

  Abstract A general and practical chemistry route to the synthesis of compounds containing two 4H‐pyrans or two tetraketones in aqueous media is described. This method provides several advantages such as neutral conditions, high yields, and simple workup procedure. In addition, water was chosen as a green solvent.

  摘要描述了在水性介质中合成含有两个 4H-吡喃或两个四酮的化合物的通用和实用的化学途径。这种方法提供了几个优点，例如中性条件、高产率和简单的后处理程序。此外，选择水作为绿色溶剂。
• 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。
• Synthesis and characterization of the immobilized Ni–Zn–Fe layered double hydroxide (LDH) on silica-coated magnetite as a mesoporous and magnetically reusable catalyst for the preparation of benzylidenemalononitriles and bisdimedones (tetraketones) under green conditions
  作者：Masumeh Gilanizadeh、Behzad Zeynizadeh

  DOI：10.1039/c8nj00788h

  日期：——

  Magnetic Fe₃O₄@SiO₂@Ni–Zn–Fe LDH was prepared as an efficient nanocatalyst for the Knoevenagel and tandem Knoevenagel–Michael reactions to afford the products in water.

  磁性Fe3O4@SiO2@Ni-Zn-Fe LDH被制备为Knoevenagel和串联Knoevenagel-Michael反应的高效纳米催化剂，以在水中得到产物。
• Chemoselective synthesis of xanthenes and tetraketones in a choline chloride-based deep eutectic solvent
  作者：Najmedin Azizi、Sahar Dezfooli、Mohammad Mahmoudi Hashemi

  DOI：10.1016/j.crci.2013.05.002

  日期：2013.11

  Résumé A chemoselective synthesis of tetraketone and xanthene derivatives, by means of tandem Knoevenagel condensation and Michael addition in choline chloride-based deep eutectic solvents (DESs), is presented. The reaction of readily available aldehydes and active methylene compounds in malonic acid- and ZnCl2-based DES gives various xanthenes derivatives with good to excellent yields under mild reaction conditions. On the other hand, tetraketones were synthesized in almost quantitative yields by simple condensation of an aldehyde and active methylene compounds in milder deep eutectic solvents of urea and SnCl2. In addition, the reaction of other types of choline chloride-based DES leads to a mixture of tetraketone and xanthene.

  摘要 本文介绍了一种通过基于氯化胆碱的深共熔溶剂（DES）中的串联Knoevenagel缩合和Michael加成反应，实现四酮和咕吨衍生物的化学选择性合成方法。在温和反应条件下，将易获得的醛和活性亚甲基化合物在基于丙二酸和ZnCl2的DES中反应，得到了多种咕吨衍生物，产率良好至优秀。另一方面，通过在更温和的基于尿素和SnCl2的深共熔溶剂中简单地缩合醛和活性亚甲基化合物，合成了几乎定量产率的四酮。此外，其他类型的基于氯化胆碱的DES反应产生四酮和咕吨的混合物。
• Sulfuric acid-modified PEG-6000 (PEG–OSO3H): a biodegradable, reusable solid acid catalyst for highly efficient and eco-friendly synthesis of novel bis-Knoevenagel products under solvent-free conditions
  作者：Zeba N. Siddiqui、Tabassum Khan

  DOI：10.1016/j.tetlet.2013.05.012

  日期：2013.7

  PEG-6000 (PEG–OSO3H) is used as a highly efficient, biodegradable, and reusable acid catalyst for the synthesis of novel acyclic and heterocyclic bis-Knoevenagel products under thermal solvent-free conditions. The remarkable features of this green, new methodology are high conversions, cleaner reaction profile, simple experimental and work-up procedure, and economic viability. The catalyst is characterized

  硫酸改性的PEG-6000（PEG-OSO 3 H）被用作高效，可生物降解和可重复使用的酸催化剂，用于在无热溶剂的条件下合成新型无环和杂环双-Knoevenagel产品。这种绿色的新方法的显着特点是高转化率，更清洁的反应曲线，简单的实验和后处理程序以及经济可行性。首次通过SEM-EDX和粉末XRD对催化剂进行了表征。催化剂可以重复使用几次，而不会显着降低其催化活性。