CAS: 826-45-9; Bicyclo[2.2.2]Octane-1,4-Diyldimethanol

该化合物是双环有机化合物,其独特结构由两环[2.2.2]octane框架组成,在1和4位置上有两组氢氧甲基(-CH2OH),一般无色可粉黄黄色液体或固体,视温度和纯度而定;由于氢氧基组的存在,它具有中度极极分性,可参与氢结合,影响极地溶剂中的溶解性;Bicylo[2.2.2.2]OCtane-1-4-dim乙醇在各种化学应用中具有意义,包括作为有机合成和材料科学的一个潜在构件,其独特的结构特征可能带来有趣的物理和化学特性,例如稳定性和回活动,使其成为有机化学领域研究的主体;此外,它可能被用于聚合化学,并作为其他化学转化的前体,突出其在研究和工业应用中的重要性.

结构式图片

相似化合物

711-02-4 1459-96-7 18720-35-9

物理性质

MSDS等安全信息

上下游产品

CAS号711-02-4 双环[2.2.2]辛烷-1,4-二羧酸 | CAS号1659-75-2 双环[2.2.2]辛烷-1,4... | CAS号28305-83-1 (1-methyl-4-bic... | CAS号828-52-4 4-(羟基甲基)双环[2.2.... | CAS号898-81-7 [1-[(4-methylph...

合成工艺路线路线简述

  • 1459-96-7 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C
    标题:Symmetry And Dynamics Of Molecular Rotors In Amphidynamic Molecular Crystals
    作者:Karlen,Steven D.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2010 卷标:107(34) 页码:14973-14977]

    1659-75-2 = 826-45-9 [标题:Reaction Conditions
    标题:Unexpectedly Similar Charge Transfer Rates Through Benzo-Annulated Bicyclo[2.2.2]Octanes
    作者:Goldsmith,Randall H.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(24) 页码:7659-7669]

    1659-75-2 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether; 4 H,Reflux1.2 Reagents: Sodium Hydroxide Solvents: Water
    标题:Novel Vitamin D Receptor Ligands Bearing A Spherical Hydrophobic Core Structure-Comparison Of Bicyclic Hydrocarbon Derivatives With Boron Cluster Derivatives
    作者:Wongmayura,Angsuma; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2012 卷标:22(4) 页码:1756-1760]

    830-28-4 = 826-45-9
    反应条件:1.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Diethylene Glycol; 48 H,Reflux
    标题:Ultra-Fast Rotors For Molecular Machines And Functional Materials Via Halogen Bonding: Crystals Of 1,4-Bis(Iodoethynyl)Bicyclo[2.2.2]Octane With Distinct Gigahertz Rotation At Two Sites
    作者:Lemouchi,Cyprien; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(16) 页码:6371-6379]

    830-28-4 = 826-45-9
    反应条件:1.1 Reagents: Sodium Hydroxide,Sodium Hydroxide-D Solvents: Triethylene Glycol; 36 H,210 °C; 210 °C -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Ultrafast Rotation In An Amphidynamic Crystalline Metal Organic Framework
    作者:Vogelsberg,Cortnie S.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2017 卷标:114(52) 页码:13613-13618]

    1686-98-2 = 826-45-9
    反应条件:1.1 -2.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    843-52-7 = 826-45-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; Reflux2.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Ethylene Glycol; Reflux
    标题:Molecular Rods: Facile Desymmetrization Of 1,4-Diethynylbicyclo[2.2.2]Octane
    作者:Kaleta,Jiri; Et Al
    参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(37) 页码:5137-5142]

    843-52-7 = 826-45-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; 24 H,Reflux2.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Diethylene Glycol; 48 H,Reflux
    标题:Ultra-Fast Rotors For Molecular Machines And Functional Materials Via Halogen Bonding: Crystals Of 1,4-Bis(Iodoethynyl)Bicyclo[2.2.2]Octane With Distinct Gigahertz Rotation At Two Sites
    作者:Lemouchi,Cyprien; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(16) 页码:6371-6379]

    109-80-8 + 843-59-4 = 826-45-9
    反应条件:1.1 -2.1 Reagents: Hydrogen,Nickel Solvents: Ethanol; 3 D,Reflux3.1 -
    标题:Unexpectedly Similar Charge Transfer Rates Through Benzo-Annulated Bicyclo[2.2.2]Octanes
    作者:Goldsmith,Randall H.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(24) 页码:7659-7669]

    856-70-2 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether; 5 H,Reflux2.1 Reagents: Hydrochloric Acid Solvents: Water; 24 H,Reflux3.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Diethylene Glycol; 48 H,Reflux
    标题:Ultra-Fast Rotors For Molecular Machines And Functional Materials Via Halogen Bonding: Crystals Of 1,4-Bis(Iodoethynyl)Bicyclo[2.2.2]Octane With Distinct Gigahertz Rotation At Two Sites
    作者:Lemouchi,Cyprien; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(16) 页码:6371-6379]

    1659-75-2 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    898-81-7 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    88412-20-8 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    830-28-4 = 826-45-9
    反应条件:1.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Ethylene Glycol; Reflux
    标题:Molecular Rods: Facile Desymmetrization Of 1,4-Diethynylbicyclo[2.2.2]Octane
    作者:Kaleta,Jiri; Et Al
    参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(37) 页码:5137-5142]

    = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
    标题:Competitive Carbon-Oxygen Cleavage,Sulfur-Oxygen Cleavage,And Electron Transfer In The Lithium Aluminum Hydride Reduction Of Hindered Disulfonates
    作者:Wang,Shin Shin; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1985 卷标:50(5) 页码:653-6]

    174685-35-9 = 826-45-9
    反应条件:1.1 Catalysts: Nickel Solvents: Ethanol; 48 H,Reflux2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C
    标题:Symmetry And Dynamics Of Molecular Rotors In Amphidynamic Molecular Crystals
    作者:Karlen,Steven D.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2010 卷标:107(34) 页码:14973-14977]

    41034-55-3 = 826-45-9
    反应条件:1.1 Reagents: Hydrogen,Nickel Solvents: Ethanol; 3 D,Reflux2.1 -
    标题:Unexpectedly Similar Charge Transfer Rates Through Benzo-Annulated Bicyclo[2.2.2]Octanes
    作者:Goldsmith,Randall H.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(24) 页码:7659-7669]

    41034-55-3 = 826-45-9
    反应条件:1.1 -2.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    843-52-7 = 826-45-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; 3 H,Reflux; Reflux -> Rt1.2 Reagents: Potassium Hydroxide Solvents: Water; Neutralized2.1 Reagents: Sodium Hydroxide,Sodium Hydroxide-D Solvents: Triethylene Glycol; 36 H,210 °C; 210 °C -> Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Ultrafast Rotation In An Amphidynamic Crystalline Metal Organic Framework
    作者:Vogelsberg,Cortnie S.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2017 卷标:114(52) 页码:13613-13618]

    109-80-8 + 843-59-4 = 826-45-9
    反应条件:1.1 -2.1 -3.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    540-63-6 + 174685-34-8 = 826-45-9
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Chloroform; Cooled; Rt; 2 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water2.1 Catalysts: Nickel Solvents: Ethanol; 48 H,Reflux3.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C
    标题:Symmetry And Dynamics Of Molecular Rotors In Amphidynamic Molecular Crystals
    作者:Karlen,Steven D.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2010 卷标:107(34) 页码:14973-14977]

    = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 1 H,Rt; 2.5 H,Reflux; Reflux -> Rt1.2 Reagents: Water; Rt2.1 Reagents: Hydrochloric Acid Solvents: Water; 3 H,Reflux; Reflux -> Rt2.2 Reagents: Potassium Hydroxide Solvents: Water; Neutralized3.1 Reagents: Sodium Hydroxide,Sodium Hydroxide-D Solvents: Triethylene Glycol; 36 H,210 °C; 210 °C -> Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Ultrafast Rotation In An Amphidynamic Crystalline Metal Organic Framework
    作者:Vogelsberg,Cortnie S.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2017 卷标:114(52) 页码:13613-13618]

    540-63-6 + 843-59-4 = 826-45-9
    反应条件:1.1 -2.1 -3.1 Reagents: Lithium Aluminum Hydride
    标题:Synthesis,Characterization,And Chemistry Of Bridgehead-Functionalized Bicyclo[2.2.2]Octanes: Reactions At Neopentyl Sites
    作者:Kumar,Kanta; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(4) 页码:665-70]

    856-70-2 = 826-45-9
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether; Reflux2.1 Reagents: Hydrochloric Acid Solvents: Water; Reflux3.1 Reagents: Potassium Hydroxide,Hydrazine Hydrate (1:1) Solvents: Ethylene Glycol; Reflux
    标题:Molecular Rods: Facile Desymmetrization Of 1,4-Diethynylbicyclo[2.2.2]Octane
    作者:Kaleta,Jiri; Et Al
    参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(37) 页码:5137-5142
📜1,4-环己二酮-2,5-二甲酸二乙酯置于lithium Aluminium Tetrahydride体系中,化学反应生成 双环[2.2.2]辛烷-1,4-二甲醇
参考文献:葫芦[7]脲与双环[2.2.2]辛烷和金刚烷客体的新型超高亲和力主客体复合物:M2亲和力计算的热力学分析和评价
标题:葫芦[7]脲与双环[2.2.2]辛烷和金刚烷客体的新型超高亲和力主客体复合物:M2亲和力计算的热力学分析和评价
摘要:先前已显示双阳离子二茂铁衍生物以超高亲和力 (δg(O) =-21 Kcal/mol) 结合水中的葫芦 [7] 脲 (Cb[7]).在这里,我们描述了同样能很好地结合水性 Cb[7] 的新化合物,验证了我们之前的建议,即它们也将是超高亲和力的 Cb[7] 客体.目前的客体基于双环 [2.2.2] 辛烷或金刚烷核,没有金属原子,因此这些结果也证实了基于二茂铁的客体的显着高亲和力不需要归因于金属特异性相互作用.因为我们在合成之前使用了 M2 方法来计算几个新的主客体系统的亲和力,所以目前的结果也提供了这种计算方法的第一次盲评估.盲法计算与实验相当吻合,并成功再现了观察结果,即新的基于金刚烷的客体实现了极高的亲和力,尽管它们仅在 Cb[7] 主体的一个带电负性入口处定位了阳离子取代基.然而,也存在与实验的显着偏差,这些偏差导致程序错误的校正和计算对分子能量参数物理合理变化的敏感性的指导性评估.
DOI:10.1021/ja109904U

海关参考信息

专利信息


专利号:US-11518726-B2
优先权日:2017-10-11
标题 :Synthesis of bicyclo[2.2.2]octane derivatives
发明人：HU YUE RACHEL; HEMBRE ROBERT THOMAS; TUSTIN GERALD CHARLES; LIU ZHUFANG; ADAMS STEVEN J
权利人:EASTMAN CHEM CO
摘要:Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

专利号:EP-3694831-A1
优先权日:2017-10-11
标题:Synthesis of bicyclo[2.2.2]octane derivatives

专利号:WO-2019075004-A1
优先权日:2017-10-11
标 题:SYNTHESIS OF BICYCLO [2.2.2] OCTANE DERIVATIVES

专利号:CN-111433181-A
优先权日:2017-10-11
标题 :Synthesis of Bicyclo[2.2.2]octane Derivatives

专利号:US-2020270191-A1
优先权日:2017-10-11
标 题 :Synthesis of bicyclo[2.2.2]octane derivatives

专利号:CN-111433181-B
优先权日:2017-10-11
标题:Synthesis of Bicyclo[2.2.2]octane Derivatives

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合成参考文献


参考文献:10.1007/0-306-47117-5_8
摘要:Wood BR, Hamilton SC. Large Cyclic Esters and Ether-Esters. 2002. In: Cyclic Polymers. : Kluwer Academic Publishers; 2002.
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