2,2'-(naphthalen-1-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) | 401633-56-5

• 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'-(naphthalen-1-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)
• 英文别名: 3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-naphthalen-1-ylmethyl]-5,5-dimethylcyclohex-2-en-1-one
• CAS: 401633-56-5
• 化学式: C₂₇H₃₀O₄
• 分子量: 418.533
• InChiKey: IBKOHUCTIPFGMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(naphthalen-1-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) 在 盐酸 、 氯磺酸 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 4-(3,3,6,6-Tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-naphthalene-1-sulfonyl chloride
  参考文献：
  名称：

  Cremlyn, Richard J.; Saunders, David, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 81, # 1-4, p. 73 - 82

  摘要：

  DOI：
• 作为产物：
  描述：

  1-naphthaldehyde tosylhydrazone 、 5,5-二甲基-1,3-环己二酮 以 甲苯 为溶剂， 反应 4.0h， 以84%的产率得到2,2'-(naphthalen-1-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)
  参考文献：
  名称：

  Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound

  摘要：

  N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presence of a base, the coupling reaction generates beta-keto enol ether as the major product in a polar aprotic solvent. N-Tosylhydrazone can also be converted to xanthenedione in high yields in one-pot operation under mild acidic conditions. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.02.001

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。
• Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland−Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence:  Scope and Applications of Organocatalytic Biomimetic Reductions
  作者：Dhevalapally B. Ramachary、Mamillapalli Kishor

  DOI：10.1021/jo070277i

  日期：2007.7.1

  practical and novel organocatalytic chemo- and enantioselective process for the cascade synthesis of highly substituted 2-alkyl-cyclohexane-1,3-diones and Wieland−Miescher (W−M) ketone analogs is presented via reductive alkylation as a key step. First time, we developed the one-step alkylation of dimedone and 1,3-cyclohexanedione with aldehydes and Hantzsch ester through an organocatalytic reductive alkylation

  通过还原烷基化，提出了一种实用且新颖的有机催化化学和对映选择性工艺，用于级联合成高度取代的2-烷基-环己烷-1,3-二酮和Wieland-Miescher（WM）酮类似物，这是关键步骤。首次，我们通过有机催化还原烷基化策略开发了二醛和1,3-环己二酮与醛和Hantzsch酯的一步烷基化。l的直接组合CH酸（二甲酮和1,3-环己烷二酮），醛，汉茨sch酯和甲基乙烯基酮的脯氨酸催化的级联Knoevenagel /加氢和级联的Robinson环氧化反应提供了高官能度的W-M酮类似物，并具有良好的收率。优异的对映选择性。许多还原性烷基化产物直接显示在药物化学中。
• Nickel nanoparticles: A highly efficient catalyst for one pot synthesis of tetraketones and biscoumarins
  作者：JITENDER M. KHURANA、KANIKA VIJ

  DOI：10.1007/s12039-012-0275-8

  日期：2012.7

  nickel nanoparticles have been used as a catalyst for promoting the synthesis of 2,2′-aryl-methylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one), 2,2′-aryl-methylene bis(3-hydroxy-2-cyclohexene-1-one), also known as tetraketones, and biscoumarins via Knoevenagel condensation followed by rapid Michael addition. A novel and highly efficient PVP stabilized Ni nanoparticle catalysed synthesis of tetraketones

  设计了一种新颖且实用的方案，其中聚乙烯吡咯烷酮（PVP）稳定的镍纳米颗粒已用作催化剂，以促进2,2'-芳基-亚甲基双（3-羟基-5,5-二甲基- 2-环己烯-1-酮），2,2'-芳基-亚甲基双（3-羟基-2-环己烯-1-酮）和双香豆素通过Knoevenagel缩合，然后快速添加迈克尔。 已经描述了在室温下在乙二醇中新颖和高效的PVP稳定的Ni纳米颗粒催化的四酮和双香豆素的合成。
• Domino Knoevenagel/Michael synthesis of 2,2’-arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one) derivatives catalyzed by silica-diphenic acid and their single crystal X-ray analysis
  作者：RUPALI VAID、MONIKA GUPTA、RAJNI KANT、VIVEK K GUPTA

  DOI：10.1007/s12039-016-1088-y

  日期：2016.6

  An efficient and eco-friendly procedure has been developed for the synthesis of various 2,2’-arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives which were isolated and characterized by melting point, IR, 1H-NMR, 13C-NMR and mass spectrometric techniques. Out of the fourteen compounds synthesized, four compounds yielded crystals suitable for single crystal X-ray analysis which

  已开发出一种有效且环保的方法，用于合成各种2,2'-芳基亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-酮）衍生物，这些衍生物经分离并以熔点为特征， IR，1 H-NMR，13 C-NMR和质谱技术。在合成的14种化合物中，有4种化合物产生的晶体适合单晶X射线分析，表明2,2'-苯基亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-酮）在其中结晶。空间群为I 4 1 / a的四方体系在空间群为P的单斜晶系中结晶，2,2'-（3-硝基苯基）亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-一）结晶。2 1 / n，2,2'-（4-硝基苯基）亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-酮）在正交晶系中以Pca21和2,2'-（4 -氯苯基）亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-酮）在单斜空间群P21 / c中结晶。 据报道，在研磨过程中，不同的醛类与二甲酮反应，可以有效地合成二氧化硅-二苯甲酸催化的2
• An eco-friendly approach to synthesize arylmethylene bis(3-hydroxy-5,5’-dimethyl-2-cyclohexene-1-ones) and 1,8-dioxo-octahydroxanthenes
  作者：Swati D. Jadhav、Bhagyashree M. Patil、Suresh S. Patil

  DOI：10.1007/s11164-024-05274-w

  日期：——

  A new method has been proposed for the green and efficient synthesis of xanthenediones and their corresponding open-chain analogs aryl-methylene bis(3-hydroxy-5,5’-dimethyl-2-cyclohexene-1-ones) using natural acid, Lemon juice, as the catalyst. This method involves the use of lemon juice as a surfactant-type bronsted acid, which makes it non-polluting and produces a high-purity product with excellent

  提出了一种利用天然酸柠檬绿色高效合成呫吨二酮及其相应开链类似物芳基亚甲基双(3-羟基-5,5'-二甲基-2-环己烯-1-酮)的新方法果汁作为催化剂。该方法使用柠檬汁作为表面活性剂型布朗斯台德酸，使其无污染，且产品纯度高，收率优异。此外，后处理程序干净、简单。双甲酮和醛是该过程的起始原料。 图形概要