2-Methyl-5,8-aethano-4a,5,8,8a-tetrahydro-1,4-naphthochinon | 93139-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-5,8-aethano-4a,5,8,8a-tetrahydro-1,4-naphthochinon
• 英文别名: 4-Methyltricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione；4-methyltricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione
• CAS: 93139-46-9
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: GXHQCAHONVGRCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲基苯醌 、 1,3-环己二烯 在 1-hexadecyl-3-methylimidazolium chloride/MCM-48 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以91%的产率得到2-Methyl-5,8-aethano-4a,5,8,8a-tetrahydro-1,4-naphthochinon
  参考文献：
  名称：

  Metal-free activation of C–C multiple bonds through halide ion pairs: Diels–Alder reactions with subsequent aromatization

  摘要：

  Imidazolium and ammonium halides, both in homogeneous phase or immobilized on mesoporous silica, proved able to promote the aromatization reaction of Diels-Alder adducts under ethylene and H(2) elimination. These observations point to the increased nucleophilicity of such halide ions. They also open the possibility to employ such ion pairs as nucleophilic organocatalysts, for example, as substitutes for phosphines or amines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.027

文献信息

• STRONGLY LEWIS ACIDIC METAL-ORGANIC FRAMEWORKS FOR CONTINUOUS FLOW CATALYSIS
  申请人：The University of Chicago

  公开号：US20210053042A1

  公开（公告）日：2021-02-25

  Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

  描述了包含三氟甲磺酸盐配位金属节点的Lewis酸性金属有机框架（MOF）材料。这些材料可用作广泛范围的有机基团转化中的杂质催化剂，包括Diels-Alder反应、环氧化物开环反应、Friedel-Crafts酰化反应和烯烃水解烷氧基化反应。这些MOF还可以通过金属化有机桥联配体制备，以提供串联反应的杂质催化剂和/或与支撑颗粒制备为复合材料，用于连续流反应器系统的柱中。还描述了制备和使用MOF材料及其复合材料的方法。
• Metal-free activation of C–C multiple bonds through halide ion pairs: Diels–Alder reactions with subsequent aromatization
  作者：Helena Kaper、Markus Antonietti、Frédéric Goettmann

  DOI：10.1016/j.tetlet.2008.05.027

  日期：2008.7

  Imidazolium and ammonium halides, both in homogeneous phase or immobilized on mesoporous silica, proved able to promote the aromatization reaction of Diels-Alder adducts under ethylene and H(2) elimination. These observations point to the increased nucleophilicity of such halide ions. They also open the possibility to employ such ion pairs as nucleophilic organocatalysts, for example, as substitutes for phosphines or amines. (c) 2008 Elsevier Ltd. All rights reserved.