CAS: 92050-16-3; 5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydronaphthalen-2-Amine

该化合物是一种替代的四氢甲二烯衍生物,具有芳香芳烃功能组别,其僵硬,严酷的阻力结构增强了稳定性,适合需要受控反应的用途;该化合物的四甲基替代模式有助于其亲脂性,有利于有机合成和材料科学的利用;其矿物质组允许其进一步功能化,使其能够融入更为复杂的分子结构;该化合物在制药和农用化学研究中特别有用,其结构框架可以作为关键的中间体;高纯度确保合成应用的一致性.

结构式图片

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合成工艺路线路线简述

  • 102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 2 - 5 Bar,70 °C
    标题:Dihydroindene And Tetrahydronaphthalene Compounds For Treating Disease
    参考文献:United States]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 2 - 5 Bar,70 °C
    标题:Preparation Of Pentamethyltetrahydronaphthalene Derivatives For Use As Human Retinoid X Receptor Modulators
    参考文献:World Intellectual Property Organization]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Stannous Chloride Solvents: Ethanol; 12 H,Reflux1.2 Reagents: Sodium Hydroxide Solvents: Water
    标题:Selective Alkylation Of βii-Tubulin And Thioredoxin-1 By Structurally Related Subsets Of Aryl Chloroethylureas Leading To Either Anti-Microtubules Or Redox Modulating Agents
    作者:Fortin,Jessica S.; Cote,Marie-France; Lacroix,Jacques; Desjardins,Michel; Petitclerc,Eric; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2008 卷标:16(15) 页码:7277-7290]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 24 H,25 °C
    标题:Methods For The Production And Use Of Tricyclic Retinoids
    参考文献:European Patent Organization]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol; 6 H,70 °C
    标题:Synthesis Of Tamibarotene
    作者:Bian,Haiyong; Xu,Wenfang
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2009 卷标:40(1) 页码:9-11]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 15 H,1 Atm,Rt
    标题:Preparation Of Tetrahydronaphthalenylureidobenzoic Acids As Retinoid Agonists.
    参考文献:United States]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; Overnight,Rt
    标题:Methods To Generate An Array Of Novel Rexinoids By Sar On A Potent Retinoid X Receptor Agonist: A Case Study With Net-Tmn
    作者:Wagner,Carl E.; Jurutka,Peter W.
    参考文献:Methods In Molecular Biology (New York 日期:2019 卷标:2019 页码:109-121]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 1 H,Rt
    标题:Retinoid Compounds With Retinoic Acid Receptor Agonist Activity
    参考文献:World Intellectual Property Organization]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 1 H,Rt
    标题:Heterocyclic Compounds As Retinoid X Receptor Modulators,And Drugs And Pharmaceutical Compositions Containing Them
    参考文献:Japan]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
    标题:Aza-Retinoids As Novel Retinoid X Receptor-Specific Agonists
    作者:Farmer,Luc J.; Marron,Kristen S.; Canan Koch,Stacie S.; Hwang,C. K.; Kallel,E. Adam; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2006 卷标:16(9) 页码:2352-2356]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 2 - 5 Bar,70 °C
    标题:Modeling,Synthesis,And Biological Evaluation Of Potential Retinoid X Receptor (Rxr)-Selective Agonists: Analogues Of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-Tetrahydro-2-Naphthyl)Ethynyl]Benzoic Acid (Bexarotene) And 6-(Ethyl(5,5,8,8-Tetrahydronaphthalen-2-Yl)Amino)Nicotinic Acid (Net-Tmn)
    作者:Heck,Michael C.; Wagner,Carl E.; Shahani,Pritika H.; Macneill,Mairi; Grozic,Aleksandra; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2016 卷标:59(19) 页码:8924-8940]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Ammonium Formate Catalysts: Palladium Solvents: Methanol; 2 H,Reflux
    标题:Palladium-Catalyzed Synthesis Of Aromatic Carboxylic Acids With Silacarboxylic Acids
    作者:Friis,Stig D.; Andersen,Thomas L.; Skrydstrup,Troels
    参考文献:Organic Letters 日期:2013 卷标:15(6) 页码:1378-1381]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 24 H,25 °C
    标题:Preparation Of Tricyclic Retinoids As Retinoid Receptor Agonists
    参考文献:United States]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; Rt
    标题:Design And Synthesis Of Novel Retinoid Synergists Having A Dibenzodiazepine Skeleton
    作者:Ohta,Kiminori; Kawachi,Emiko; Shudo,Koichi; Kagechika,Hiroyuki
    参考文献:Heterocycles 日期:2010 卷标:81(11) 页码:2465-2470]

    139162-43-9 = 92050-16-3
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Glycerol; 2 H,150 °C
    标题:Method For Synthesizing 5,6,7,8-Tetrahydro-5,5,8,8-Tetramethyl-2-Naphthylamine
    参考文献:China]

    6683-46-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydroxyamine Hydrochloride,Sulfuric Acid Solvents: Acetonitrile; 25 °C; 10 Min,25 °C1.2 Reagents: Hydrochloric Acid,Titanium Chloride (Ticl3) Solvents: Water; 25 °C; 10 Min,25 °C1.3 Reagents: Citric Acid,Sodium Salt,Sodium Hydroxide Solvents: Water; Basified,25 °C
    标题:C-H Amination Of Arenes With Hydroxylamine
    作者:See,Yi Yang; Sanford,Melanie S.
    参考文献:Organic Letters 日期:2020 卷标:22(8) 页码:2931-2934]

    139162-43-9 = 92050-16-3
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 4 H,Reflux
    标题:Process Improvement Of Tamibarotene Preparation
    作者:Zhao,Ming-Zhu; Zang,Cheng-Xu; Cai,Zhan; Jiang,Zhi-Hui; Huang,Jing-Hua; Et Al
    参考文献:Yaoxue Shijian Zazhi 日期:2012 卷标:30(4) 页码:287-288]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 15 H,Rt
    标题:Preparation Of N-(Tetrahydronaphthyl)-N'-Phenylureas As Retinoid Agonists For Treatment Of Emphysema,Cancer,Or Dermatological Disorders
    参考文献:World Intellectual Property Organization]

    102121-55-1 = 92050-16-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 15 H,1 Atm,Rt
    标题:Preparation Of N-(Tetrahydronaphthyl)-N'-Arylureas As Retinoid Agonists For Treatment Of Emphysema,Cancer,Or Dermatological Disorders
    参考文献:World Intellectual Property Organization
5,5,8,8-四甲基-5,6,7,8-四氢-2-萘羧酸置于sodium Azide,硫酸体系中,用 氯仿 作为反应溶剂,化学反应生成 5,6,7,8-四氢-5,5,8,8-四甲基-2-萘胺
参考文献:Isolation And Proof Of Structure Of 1,1,4,4-Tetramethyl-6-T-Butyl-1,2,3,4-Tetrahydronaphthalene1
标题:Isolation And Proof Of Structure Of 1,1,4,4-Tetramethyl-6-T-Butyl-1,2,3,4-Tetrahydronaphthalene1
摘要:
DOI:10.1021/jo01075A008

海关参考信息

专利信息


专利号:CN-103664680-A
优先权日:2012-09-26
标 题:A new process for the synthesis of Tamibarotene

专利号:US-5214202-A
优先权日:1990-03-20
标 题:Method for preparing benzoic acid derivatives
发明人:HAMADA YOSHINORI; YAMADA ISAMU; UENAKA MASAAKI; SAKATA TERUO
权利人:SHIONOGI & CO
摘要:This invention relates to a synthesis method favorable for the industrial production of a benzoic acid derivative having a retinoid activity of the general formula: ##STR1## wherein the derivative can be obtained by a simple procedure in safety with high yield. n Specifically, this invention relates to a synthesis method characterized in that only one vessel is needed for several reactions in the different steps of subjecting acetanilide as a starting material, which is readily available and safe to handle, to Friedel-Crafts reaction with 2,5-dimethyl-2,5-dichlorohexane; subjecting the thus obtained compound to acyl exchange reaction with monomethyl ester terephthalic chloride, followed by hydrolysis; and recrystallizing from a mixture of methanol and water. n Moreover, the crystals in novel form obtained by the synthesis method of this invention are suitable for formulation, because the amount of solvents remaining therein after recrystallization is small and the grain size thereof is uniform.
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合成参考文献


参考文献:10.1055/s-0039-1690707
摘要:Du F, Zhou Q, Fu Y, Chen Y, Wu Y, Chen G. Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol. Synlett. 2019 Oct 16;30(19):2161–8. doi: 10.1055/s-0039-1690707.
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