1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone | 55431-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone
• 英文别名: 1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthracene-9,10-dione；1,2,3,4,4a,9a-Hexahydro-1,4-aetheno-anthracen-9,10-dion；9.10-Dioxy-1.4-aethylen-1.4-dihydro-anthracen；1,4,4a,9a-Tetrahydro-1,4-ethanoanthracene-9,10-dione；tetracyclo[10.2.2.02,11.04,9]hexadeca-4,6,8,13-tetraene-3,10-dione
• CAS: 55431-77-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: UUILUGXGLYHBPX-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone 在 1-hexadecyl-3-methylimidazolium chloride/MCM-48 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以40%的产率得到蒽醌
  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
• 作为产物：
  描述：

  1,3-环己二烯 、 1,4-萘醌 生成 1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone
  参考文献：
  名称：

  4b，5、12、12a-四氢-5、12-乙基-13 H-茚并[2,3- b ]蒽，4b，5、10、10a-四氢-5,10 - ethano -11 H的合成-茚并[2,3- b ]萘的和-1,2,3，9α-二六氢-1,4-（围绝经期naphthaleno）-fluorenes

  摘要：

  合成内切-和外切-13-氧4B，图5，图12，图12a-四氢5,12-ethanoindeno [2,3- b ]蒽（23 ;方案1和2），外切-和内切-11 -oxo-4b，5、10、10a-四氢-5、10-乙基茚并[2,3- b ]萘（31 ;方案3），1,2,3,4,4a，9a-hexahydro-1 ，4-（围naphthaleno）芴-9-酮（36 ;方案4），以及立体异构酮对相应的烃23和36，进行说明。

  DOI：

  10.1002/hlca.19750580208

文献信息

• Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors
  作者：Allimuthu T. Dharmaraja、Mallika Alvala、Dharmarajan Sriram、Perumal Yogeeswari、Harinath Chakrapani

  DOI：10.1039/c2cc35343a

  日期：——

  Here, we report 5-hydroxy-1,2,3,4,4a,9a-hexahydro-1,4-ethano-9,10-anthraquinone (13), a small molecule generating reactive oxygen species (ROS) in pH 7.4 buffer under ambient aerobic conditions that has selective and potent Mycobacterium tuberculosis growth inhibitory activity.

  在此，我们报告了5-羟基-1,2,3,4,4a,9a-六氢-1,4-乙烯-9,10-蒽醌（13），这是一种在pH 7.4缓冲液中、在常温好氧条件下生成活性氧（ROS）的小分子，具有选择性和强效的抗结核分枝杆菌生长抑制活性。
• Ionic liquids as powerful media in scandium triflate catalysed Diels–Alder reactions: significant rate acceleration, selectivity improvement and easy recycling of catalyst
  作者：Choong Eui Song、Eun Joo Roh、Sang-gi Lee、Woo Ho Shim、Jung Hoon Choi

  DOI：10.1039/b101140p

  日期：——

  Ionic liquids act as powerful media (or additives) in scandium triflate catalysed Diels–Alder reactions not only for facilitating of catalyst recovery but also for accelerating reaction rate and improving selectivity.

  离子液体在三氟甲磺酸钪催化的 Diels-Alder 反应中充当强大的介质（或添加剂），不仅有助于催化剂回收，而且有助于加快反应速率和提高选择性。
• meso-Tetraphenylporphyrin with a pi-system extended by fusion with anthraquinone
  作者：Mikhail A. Filatov、Ernesta Heinrich、Katharina Landfester、Stanislav Baluschev

  DOI：10.1039/c5ob00884k

  日期：——

  Fusion of a porphyrin with anthraquinone through the synthesis of a suitably substituted pyrrole that can be cyclotetramerized and the optical properties of the resulting molecular system are described.

  通过合成适当取代的吡咯并进行环四聚化，将卟啉与蒽醌融合，并描述所得分子系统的光学性质。
• Diels; Alder, Chemische Berichte, 1929, vol. 62, p. 2357
  作者：Diels、Alder

  DOI：——

  日期：——
• Hydrothermal synthesis of imidazole functionalized carbon spheres and their application in catalysis
  作者：Rezan Demir-Cakan、Philippe Makowski、Markus Antonietti、Frederic Goettmann、Maria-Magdalena Titirici

  DOI：10.1016/j.cattod.2009.05.003

  日期：2010.2

  We describe the production and catalytic application of highly functionalized mesoporous carbonaceous materials, obtained via a one step green and cheap process relying on the hydrothermal carbonization of carbohydrates (e.g. glucose) in the presence of functional organic monomers (e.g. vinyl imidazole). The resulting materials could be further functionalized to feature imidazolium bromides on their surface and be used for various transesterification, Knoevenagel and Aldol reactions. (C) 2009 Elsevier B.V. All rights reserved.