CAS: 928-91-6; Cis-4-Hexen-1-Ol

该化合物是六碳不饱和酒精,4号站点有精密的双重结合物,其特点是新鲜的绿色味,成为香味和口味应用中宝贵的中间体,其结构允许有机合成中选择性反应,特别是在氢化或氧化反应中.Cis-conformation有助于其独特的嗅觉特性,使其与跨异构体相区别.在普通有机溶剂中,Cis-4-Hexen-1-ol具有中度挥发性和溶性,适于用于精细的化学制剂.在受控制的条件下,其纯度和稳定性确保了工业和实验室环境的一贯性能.

结构式图片

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928-92-7 35194-36-6 57074-37-0

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合成工艺路线路线简述

  • 13894-60-5 = 928-91-6
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether; Rt; 30 Min,Rt1.2 Reagents: Ethyl Acetate; Rt
    标题:Unsaturated C18 Fatty Acids And Their Uses In Therapy
    参考文献:World Intellectual Property Organization]

    110-87-2 = 928-91-6
    反应条件:1.1 Reagents: Methylmagnesium Bromide Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether,Toluene
    标题:Enantioselective Ring Construction With Control Of Side-Chain Stereochemistry. Synthesis Of (+)-Isoneonepetalactone
    作者:Taber,Douglass F.; Amedio,John C. Jr.; Raman,Krishna
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(13) 页码:2984-90]

    928-93-8 = 928-91-6
    反应条件:1.1 Reagents: Quinoline,Hydrogen Catalysts: Calcium Carbonate,Palladium Solvents: Pentane
    标题:Seven-Membered Ring Synthesis Based On Arene Olefin Cycloadditions. Part Ix. The Total Synthesis Of (+/-)-Rudmollin
    作者:Wender,Paul A.; Fisher,Karl
    参考文献:Tetrahedron Letters 日期:1986 卷标:27(17) 页码:1857-60]

    = 928-91-6 [标题:Reaction Conditions
    标题:Regiochemistry And Stereochemistry Of Intramolecular [2+2] Photocycloaddition Of Carbon-Carbon Double Bonds To Cyclohexenones
    作者:Becker,D.; Nagler,M.; Sahali,Y.; Haddad,N.
    参考文献:Journal Of Organic Chemistry 日期:1991 卷标:56(14) 页码:4537-43]

    = 928-91-6 [标题:Reaction Conditions
    标题:Synthetically Useful Dianions Via Reductive Lithiation Of Tetrahydrofurans By Aromatic Radical Anions
    作者:Mudryk,Boguslaw; Cohen,Theodore
    参考文献:Journal Of The American Chemical Society 日期:1991 卷标:113(5) 页码:1866-7]

    = 928-91-6 [标题:Reaction Conditions
    标题:β-Halo Ether Synthesis Of Olefinic Alcohols: Stereochemistry Of The Ring-Scission Of 2-Substituted-3-Halotetrahydropyrans And -Furans
    作者:Crombie,Leslie; Wyvill,Robert D.
    参考文献:Journal Of The Chemical Society 日期:1985 卷标:(9) 页码:1983-95]

    = 928-91-6 [标题:Reaction Conditions
    标题:Stereoselective Syntheses Of The Isomeric 5,10-Pentadecadienals
    作者:Ohloff,Guenther; Vial,Christian; Naef,Ferdinand; Pawlak,Manfred
    参考文献:Helvetica Chimica Acta 日期:1977 卷标:60(4) 页码:1161-74]

    92975-37-6 = 928-91-6
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C; 2 H,0 °C1.2 Reagents: Water; 0 °C
    标题:Migratory Hydrogenation Of Terminal Alkynes By Base/cobalt Relay Catalysis
    作者:Liu,Xufang; Liu,Bingxue; Liu,Qiang
    参考文献:Angewandte Chemie 日期:2020 卷标:59(17) 页码:6750-6755]

    110-87-2 = 928-91-6
    反应条件:1.1 Reagents: Triphenylphosphine Catalysts: Bis(Triphenylphosphine)Nickel Dichloride Solvents: Diethyl Ether,Toluene; 15 Min,Rt1.2 Solvents: Toluene; 5 Min,20 °C; 20 °C -> 50 °C; 4 H,50 °C; 2 H,50 °C; 50 °C -> Rt1.3 Reagents: Ammonium Chloride Solvents: Water
    标题:Cis Unsaturated Esters Production For Fragrance Compositions
    参考文献:European Patent Organization]

    110-87-2 = 928-91-6
    反应条件:1.1 Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Toluene; 20 Min,Rt1.2 Overnight,90 °C; Cooled1.3 Reagents: Ammonium Chloride Solvents: Water; Rt
    标题:Mechanistic Studies Of Wacker-Type Intramolecular Aerobic Oxidative Amination Of Alkenes Catalyzed By Pd(Oac)2/pyridine
    作者:Ye,Xuan; Liu,Guosheng; Popp,Brian V.; Stahl,Shannon S.
    参考文献:Journal Of Organic Chemistry 日期:2011 卷标:76(4) 页码:1031-1044]

    166104-75-2 = 928-91-6
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane,Hexamethylphosphoramide; 20 Min,0 °C1.2 Solvents: Tetrahydrofuran; 0 °C -> Rt; 2 H,Rt1.3 Reagents: Ammonium Chloride Solvents: Water; Rt1.4 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 8 H,Rt1.5 Reagents: Ammonium Chloride Solvents: Water; Rt
    标题:Asymmetric Iodocyclization Catalyzed By Salen-Criiicl: Its Synthetic Application To Swainsonine
    作者:Kwon,Hyo Young; Park,Chul Min; Lee,Sung Bae; Youn,Joo-Hack; Kang,Sung Ho
    参考文献:Chemistry - A European Journal 日期:2008 卷标:14(3) 页码:1023-1028]

    166104-75-2 = 928-91-6
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane,Hexamethylphosphoramide; 0 °C; 20 Min,Rt1.2 Solvents: Tetrahydrofuran; 0 °C; 2 H,Rt1.3 Reagents: Ammonium Chloride Solvents: Water; Rt1.4 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 8 H,Rt1.5 Reagents: Ammonium Chloride Solvents: Water; Rt
    标题:Catalytic Enantioselective Iodocyclization Of γ-Hydroxy-Cis-Alkenes
    作者:Kang,Sung Ho; Lee,Sung Bae; Park,Chul Min
    参考文献:Journal Of The American Chemical Society 日期:2003 卷标:125(51) 页码:15748-15749]

    110-87-2 = 928-91-6
    反应条件:1.1 Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Toluene
    标题:Enantioselective Pd(Ii)-Catalyzed Aerobic Oxidative Amidation Of Alkenes And Insights Into The Role Of Electronic Asymmetry In Pyridine-Oxazoline Ligands
    作者:Mcdonald,Richard I.; White,Paul B.; Weinstein,Adam B.; Tam,Chun Pong; Stahl,Shannon S.
    参考文献:Organic Letters 日期:2011 卷标:13(11) 页码:2830-2833]

    5747-07-9 = 928-91-6
    反应条件:1.1 Reagents: Hydrogen Catalysts: Chromium Hexacarbonyl
    标题:Compounds With The Aroma Of Green Vegetables. V. Unbranched Primary Z-Alkenols
    作者:Vasil'Ev,A. A.; Cherkaev,G. V.; Nikitina,M. A.
    参考文献:Zhurnal Organicheskoi Khimii 日期:1993 卷标:29(5) 页码:889-94]

    = 928-91-6 [标题:Reaction Conditions
    标题:[2.2.1]-Bicyclic Systems Relevant To Synthetic Studies On Cp-225,917-Use Of A New Silylated Cyclopentadiene
    作者:Clive,Derrick L. J.; Cheng,Hua; Gangopadhyay,Pulak; Huang,Xiaojun; Prabhudas,Bodhuri
    参考文献:Tetrahedron 日期:2004 卷标:60(19) 页码:4205-4221]

    = 928-91-6 [标题:Reaction Conditions
    标题:An Efficient Approach To The Azaspirocyclic Structure Of Halichlorine And Pinnaic Acid
    作者:Lee,Sangku; Zhao,Zuchun
    参考文献:Tetrahedron Letters 日期:1999 卷标:40(45) 页码:7921-7924]

    = 928-91-6 [标题:Reaction Conditions
    标题:Pheromones. Xxxii. Synthons For The Preparation Of Bisolefinic Lepidoptera Pheromones
    作者:Bestmann,Hans Juergen; Koschatzky,Karl Heinrich; Schaetzke,Wilfried; Suess,Joachim; Vostrowsky,Otto
    参考文献:Liebigs Annalen Der Chemie 日期:1981 卷标:(9) 页码:1705-20]

    = 928-91-6 [标题:Reaction Conditions
    标题:Remote Functionalization By Ferrous Ion-Cupric Ion Induced Decomposition Of Alkyl Hydroperoxides
    作者:Cekovic,Z.; Dimitrijevic,L.; Djokic,G.; Srnic,T.
    参考文献:Tetrahedron 日期:1979 卷标:35(17) 页码:2021-6]

    = 928-91-6 [标题:Reaction Conditions
    标题:Reduction Of α,β-γ,δ-Unsaturated Alcohols By Lithium Aluminum Hydride
    作者:Chantegrel,Bernard; Gelin,Suzanne
    参考文献:Bulletin De La Societe Chimique De France 日期:1975 卷标:2639 页码:2639-42]

    = 928-91-6 [标题:Reaction Conditions
    标题:Radical Cyclizations. Xxv. Steric Inhibition In Formation Of A Six Carbon Ring In The Cyclization Of δ,ε Ethylenic Radicals
    作者:Julia,M.; Descoins,C.; Baillarge,M.; Jacquet,B.; Uguen,D.; Et Al
    参考文献:Tetrahedron 日期:1975 卷标:31(15) 页码:1737-44
📜2-氯甲基四氢呋喃置于lindlar'S Catalyst Lithium Amide,氢气体系中,用 正己烷,氨 作为反应溶剂,化学反应 1.0H,反应生成 顺-4-己烯-1-醇
参考文献:Regiochemistry And Stereochemistry Of Intramolecular [2+2] Photocycloaddition Of Carbon-Carbon Double Bonds To Cyclohexenones
标题:Regiochemistry And Stereochemistry Of Intramolecular [2+2] Photocycloaddition Of Carbon-Carbon Double Bonds To Cyclohexenones
摘要:The Intramolecular [2 + 2] Photocycloaddition Mechanism Of Alkenes Tethered By A Three-Methylene Chain To Cyclohexenones Has Been Studied. It Was Found That The Reversion From A 1,4-Diradical Intermediate To Starting Material Is Slow Relative To The Rate Of Photoadduct Formation. Only ''Straight'' Closure Was Observed In The Systems Studied. For Compounds 1-3 And 5,The Assumption That The First Bond Is Formed Between The Beta-Carbon Of The Enone And C-4' Leading To A 1,4-Diradical Is Supported. For The Formation Of Compounds 6-11,Possible Mechanisms Are Discussed.
DOI:10.1021/jo00014A040

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