CAS: 928-40-5; Hexane-1,5-Diol

该化合物是一个线性脂二醇,其特征为两个氢氧基(-OH)功能组,位于六碳链的第一和第二个碳原子,该化合物在室内温度下无色,粘稠液体,具有温和甜味,在水和各种有机溶剂中可溶解,使其具有多种用途. 1,5-Hexanediol主要用作聚酯和聚氨酯合成的构件,有助于树脂,涂层和塑剂的生产,其特性包括低挥发性,高热稳定性和相对较高的沸点,提高了其在工业工艺中的效用.此外,该化合物被认为毒性较低,适合用于消费品.

结构式图片

相似化合物

626-95-9 44843-89-2 103712-22-7

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合成工艺路线路线简述

  • 56-81-5 = 928-40-5 + 1191-25-9 + 627-98-5 + 111-29-5 + 626-89-1 + 4048-33-3 + 13392-69-3 + 927-55-9 + 13325-10-5 + 2508-29-4 + 629-11-8 + 110-63-4
    反应条件:1.1 Reagents: Calcium Pantothenate,Mops,Disodium Phosphate,Ferrous Sulfate,Ammonium Sulfate,Ammonium Chloride Catalysts: Acetyl Coenzyme A Acetyltransferase,Acyl Coenzyme A Dehydrogenase,3-Hydroxyacyl Coenzyme A Dehydrogenase,Alcohol Dehydrogenase,Fatty Acyl Coenzyme A Reductase (Aldehyde-Forming) Solvents: Water; 37 °C
    标题:Production Of Functionalized Carboxylic Acids And Alcohols By Reverse Fatty Acid Oxidation In Metabolically Engineered Microorganisms
    参考文献:United States]

    694-54-2 = 928-40-5
    反应条件:1.1 Solvents: Tetrahydrofuran; 0 °C
    标题:Organocatalytic Synthesis Of An Alkyltetrahydropyran
    作者:Diez,D.; Nunez,M. G.; Beneitez,A.; Moro,R. F.; Marcos,I. S.; Et Al
    参考文献:Synlett 日期:2009 卷标:(3) 页码:390-394]

    821-41-0 = 928-40-5
    反应条件:1.1 Reagents: Quinone Catalysts: Palladium,Bis(Acetonitrile)Dichloro-,Tetracarbonyl-μ-Hydro[(1,2,3,4,5-η)-1-Hydroxylato-2,3,4,5-Tetraphenyl-2,4-Cyclop... Solvents: Isopropanol,Water; 48 H,85 °C
    标题:Formal Hydration Of Non-Activated Terminal Olefins Using Tandem Catalysts
    作者:Yang,Yongsheng; Guo,Jiayi; Ng,Huimin; Chen,Zhiyong; Teo,Peili
    参考文献:Chemical Communications (Cambridge 日期:2014 卷标:50(20) 页码:2608-2611]

    = 928-40-5
    反应条件:1.1 Reagents: Sodium Monoxide,(Dimethyl Sulfide)Trihydroboron,Sodium Borohydride Solvents: Tetrahydrofuran1.2 Solvents: Water
    标题:Total Synthesis Of (+)-Brefeidin C Via An Intramolecular Allylsilane-Carbocyclization Reaction With Alpha-Substituted Allylsilanes
    作者:Neumann,Thomas
    参考文献:1995]

    823-22-3 = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Copper Oxide (Cuo),Alumina Solvents: 1,4-Dioxane; 12 H,4 Mpa,200 °C
    标题:Hydrogenation Of Biomass Lactones To Diols Over Culax/γ-Al2O3 Catalyst:The Promoting Role Of Laox
    作者:Xu,Qiu; Wang,Chungang; Shang,Zongling; Zhang,Chao; Wang,Xinchao; Et Al
    参考文献:Applied Catalysis 日期:2022 卷标:317]

    = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Rhenium,Rhodium Solvents: Water; 5 H,80 Bar,180 °C
    标题:Methods Of Producing Compounds From 5-(Halomethyl)Furfural
    参考文献:World Intellectual Property Organization]

    = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Iridium,Silica,Rhenium Oxide; 1 H,1 Mpa,473 K; 1 H,1 Mpa -> 8 Mpa,473 K
    标题:C-O Bond Hydrogenolysis Of Cyclic Ethers With Oh Groups Over Rhenium-Modified Supported Iridium Catalysts
    作者:Chen,Kaiyou; Mori,Kazuma; Watanabe,Hideo; Nakagawa,Yoshinao; Tomishige,Keiichi
    参考文献:Journal Of Catalysis 日期:2012 卷标:294 页码:171-183]

    = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Rhodium,Rhenium Oxide Solvents: Water; 4 H,8 Mpa,393 K
    标题:Mechanism Of The Hydrogenolysis Of Ethers Over Silica-Supported Rhodium Catalyst Modified With Rhenium Oxide
    作者:Koso,Shu-Ichi; Nakagawa,Yoshinao; Tomishige,Kei-Ichi
    参考文献:Journal Of Catalysis 日期:2011 卷标:280(2) 页码:221-229]

    823-22-3 = 928-40-5
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C; 16 H,20 °C1.2 Reagents: Ammonium Chloride Solvents: Water
    标题:Preparation Of P-Tefb Inhibitor-Peptidyl Linker-Integrin Binder Conjugates,Their Pharmaceutical Compositions,And Methods For The Treatment,Prevention,Or Management Of Hyperproliferative Disorder
    参考文献:World Intellectual Property Organization]

    917-64-6 + 4221-03-8 = 928-40-5
    反应条件:1.1 Solvents: Diethyl Ether; 0 °C; 2 H,0 °C -> Rt; Rt -> 0 °C1.2 Reagents: Ammonium Chloride Solvents: Water; 0 °C
    标题:First Synthesis Of A Series Of New Natural Glucosides
    作者:Qu,Meng-Nan; Zhou,Ling; Cao,Xiao-Ping
    参考文献:Chinese Journal Of Chemistry 日期:2006 卷标:24(11) 页码:1625-1630]

    = 928-40-5
    反应条件:1.1 Reagents: Phosphoric Acid,Water Solvents: Water
    标题:4-Chloro-1-Butanol And Some 1,5-Glycols
    作者:Crisan,Cornel
    参考文献:Ann. Chim. (Paris) [13] 日期:1956 卷标:1 页码:436-74]

    13984-57-1 = 928-40-5
    反应条件:1.1 Reagents: Chromia,Copper Oxide (Cuo),Hydrogen Solvents: Ethanol
    标题:Pyrrolidines,Piperidines And Hexahydroazepines From Glycols
    作者:Hill,Ralph M.; Adkins,Homer
    参考文献:Journal Of The American Chemical Society 日期:1938 卷标:60 页码:1033-5]

    823-22-3 = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Potassium Tert-Butoxide,Chloro[(1,2,3,4,5-η)-1,2,3,4,5-Pentamethyl-2,4-Cyclopentadien-1-Yl](2-Pyridineme... Solvents: Isopropanol; 15 H,5 Mpa,100 °C
    标题:Catalytic Hydrogenation Of Carboxamides And Esters By Well-Defined Cp*ru Complexes Bearing A Protic Amine Ligand
    作者:Ito,Masato; Ootsuka,Takashi; Watari,Ryo; Shiibashi,Akira; Himizu,Akio; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(12) 页码:4240-4242]

    13984-57-1 = 928-40-5
    反应条件:1.1 Reagents: Butyllithium,Triethoxysilane Catalysts: Titanocene Dichloride Solvents: Tetrahydrofuran
    标题:Ionic And Organometallic-Catalyzed Organosilane Reductions
    作者:Larson,Gerald L.; Fry,James L.
    参考文献:Organic Reactions (Hoboken 日期:2008 卷标:71 页码:1-737]

    = 928-40-5
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; 10 Min,0 °C
    标题:Enantioselective Synthesis Muqubilin And Negombatoperoxides B And C/d
    作者:Wang,Xiao-Tao; Wu,Yikang
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(5) 页码:4205-4219]

    10412-98-3 = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Carbonylchlorohydrotris(Triphenylphosphine)Ruthenium Solvents: 1,4-Dioxane,Water; 22 H,45 Bar,140 °C; 55 Bar
    标题:Process For Producing Hydroxymethyl-Alcohols
    参考文献:World Intellectual Property Organization]

    10412-98-3 = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Carbonylchlorohydrotris(Triphenylphosphine)Ruthenium Solvents: 1,4-Dioxane,Water; 22 H,45 Bar,140 °C
    标题:Ruthenium-Catalyzed Deaminative Hydrogenation Of Amino Nitriles: Direct Access To 1,2-Amino Alcohols
    作者:Calleja,Pilar; Ernst,Martin; Hashmi,A. Stephen K.; Schaub,Thomas
    参考文献:Chemistry - A European Journal 日期:2019 卷标:25(40) 页码:9498-9503]

    823-22-3 = 928-40-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Aluminum Copper Magnesium Oxide Solvents: 1,4-Dioxane; 12 H,5 Mpa,170 °C
    标题:Highly Chemoselective Hydrogenation Of Lactone To Diol Over Efficient Copper-Based Bifunctional Nanocatalysts
    作者:Wu,Jun; Gao,Guang; Li,Yong; Sun,Peng; Wang,Jia; Et Al
    参考文献:Applied Catalysis 日期:2019 卷标:245 页码:251-261]

    = 928-40-5
    反应条件:1.1 Catalysts: Cytochrome P450 Solvents: Water; 24 H,Ph 7.0,28 °C
    标题:Production Of α,ω-Alkanediols Using Escherichia Coli Expressing A Cytochrome P450 From Acinetobacter Sp. Oc4
    作者:Fujii,Tadashi; Narikawa,Tatsuya; Sumisa,Futoshi; Arisawa,Akira; Takeda,Koji; Et Al
    参考文献:Bioscience 日期:2006 卷标:70(6) 页码:1379-1385]

    = 928-40-5 [标题:Reaction Conditions
    标题:Studies On The Autoxidation Of Nonbranched Aliphatic Monocarboxylic Acids And Their Methyl Esters
    作者:Pritzkow,Wilhelm; Voerckel,Volkmar
    参考文献:Journal Fuer Praktische Chemie (Leipzig) 日期:1984 卷标:326(4) 页码:572-8]

    13984-57-1 = 928-40-5 [标题:Reaction Conditions
    标题:Reactions Induced By Pyridinium Halides. Xxv. Comparison Of The Polyreactional Transformations Induced By Pyridinium Chloride And Bromide. Case Of 1,4- And 1,5-Hexanediols
    作者:Dauzonne,Daniel; Demerseman,Pierre; Royer,Rene
    参考文献:Tetrahedron 日期:1978 卷标:34(5) 页码:529-32
📜四氢-5-甲基呋喃-2-甲醇置于氢气体系中,199.84 °C,8.0 Mpa 条件下,反应 2.0H,以3.4 Mmol的收率获得产物1,5-己二醇
参考文献:Rh改性的负载型铱催化剂对带有oh基的环状醚进行c-o键氢解
标题:Rh改性的负载型铱催化剂对带有oh基的环状醚进行c-o键氢解
摘要:在ir-reo X / Sio 2催化剂上将四氢糠醇加氢水解为1,5-戊二醇和其他相关的底物,例如3-羟基四氢呋喃和1,2-环己二醇.tof值高于rh-Reo X / Sio 2,据报道它是一种有效的催化剂.对产物的选择性(与底物中c-Oh基团相邻的c-O键解离了)与rh-Reo X / Sio 2相当或更高.除1,2-环己二醇外,大多数底物的氢解反应都是通过直接机理进行的,其中氢分子形成的氢化物会攻击c-o键的反位置.在氢解1,2-环己二醇的情况下,不利于c-o键反位的攻击,涉及脱氢成2-羟基环己酮的间接机理是导致环己醇形成的原因.
DOI:10.1016/j.Jcat.2012.07.015

海关参考信息

专利信息


专利号:US-8053522-B2
优先权日:2006-02-28
标题 :Synthesis of polyester-graft-poly(meth)acrylate copolymers
发明人:LOEHDEN GERD; BALK SVEN; BRAND THORSTEN; BRENNER GABRIELE; ARNOLD THOMAS; BAUMANN CORNELIA
权利人:EVONIK ROEHM GMBH
摘要:The present invention relates to a novel synthesis of (meth)acrylate-grafted polyesters and their action as compatibilizers.

专利号:US-6107495-A
优先权日:1996-07-24
标题:Thienylcyclohexane derivatives for thienylcyclohexyl synthesis
发明人:CAZAUX JEAN-BERNARD; DAFNIET MICHEL; KAMENKA JEAN-MARC; MANGINOT ERIC
权利人:EXPANSIA SA
摘要:PCT No. PCT/FR97/01382 Sec. 371 Date Jan. 19, 1999 Sec. 102(e) Date Jan. 19, 1999 PCT Filed Jul. 24, 1997 PCT Pub. No. WO98/03498 PCT Pub. Date Jan. 29, 1998Novel thienylcyclohexane derivatives of general formula (I), wherein R' is the 2-thienyl or 3-thienyl radical, R is the cyano radical or a radical of formula -C(O)A, and R2'' is a saturated or unsaturated optionally cyclic hydrocarbon radical, or an aryl radical, are disclosed. Methods for preparing said compounds, and the use thereof as novel industrial products for the synthesis of thienylcyclohexyl derivatives, are also disclosed.

专利号:US-10336912-B2
优先权日:2014-08-01
标 题 :Methods for producing and using aqueous polyurethane/polyacrylate hybrid dispersions and use of said aqueous polyurethane/polyacrylate hybrid dispersions in coating agents
发明人:JAHNS EKKEHARD; MANGEL TIMO; ROESCH CHRISTINE; ROMANATO PAOLA; BURK YENI; PAKUSCH JOACHIM
权利人:BASF SE
摘要:The present invention provides an aqueous polyurethane (PU)-polyacrylate hybrid dispersion obtainable by free radical polymerization of at least one acrylate polymer (A1) in the presence of at least one polyurethane (P1), a process for preparing these aqueous polyurethane-polyacrylate hybrid dispersions, wherein said process comprises a) preparing an aqueous polyurethane dispersion and b) using the polyurethane dispersion thus prepared as raw material for the further synthesis of a polyacrylate dispersion, and the use of the hybrid dispersion thus obtained as binder in filled coating materials, particularly as a binder for flexible roof coatings.

专利号:WO-2012002913-A1
优先权日:2010-07-02
标 题:Process of forming a cyclic imide
发明人:HONG SOON HYEOK; ZHANG JIAN; MUTHAIAH SENTHILKUMAR; GHOSH SUBHASH CHANDRA
权利人:UNIV NANYANG TECH; HONG SOON HYEOK; ZHANG JIAN; MUTHAIAH SENTHILKUMAR; GHOSH SUBHASH CHANDRA
摘要:A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.

专利号:US-10676422-B2
优先权日:2014-11-28
标题:Kinetic resolution of racemic hydroxy ester via asymmetric catalytic hydrogenation and application thereof
发明人:ZHOU QILIN; XIE JIANHUA; YANG XIAOHUI; WANG LIXIN
权利人:ZHEJIANG JIUZHOU PHARM CO LTD
摘要:The present invention relates to kinetic resolution of racemic δ-hydroxyl ester via asymmetric catalytic hydrogenation and an application thereof. In the presence of chiral spiro pyridyl phosphine ligand Iridium catalyst and base, racemic δ-hydroxyl esters were subjected to asymmetric catalytic hydrogenation to obtain extent optical purity chiral δ-hydroxyl esters and corresponding 1,5-diols. An optically active chiral δ-hydroxyl ester and 1,5-diols can be obtained at very high enantioselectivity and yield with relatively low usage of catalyst. The chiral δ-hydroxyl ester and 1,5-diols obtained by using the method can be used as a critical raw material for asymmetric synthesis of chiral drugs (R)-lisofylline and natural drugs (+)-civet, (−)-indolizidine 167B and (−)-coniine.

专利号:US-9045381-B2
优先权日:2010-10-19
标 题:Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof
发明人:MILSTEIN DAVID; BALARAMAN EKAMBARAM; GUNANATHAN CHIDAMBARAM; GNANAPRAKASAM BOOPATHY; ZHANG JING
权利人:MILSTEIN DAVID; BALARAMAN EKAMBARAM; GUNANATHAN CHIDAMBARAM; GNANAPRAKASAM BOOPATHY; ZHANG JING; YEDA RES & DEV
摘要:The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.

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主要参考文献

参考标题:Chemo- And Regioselective Synthesis Of Acyl-Cyclohexenes By A Tandem Acceptorless Dehydrogenation-[1,5]-Hydride Shift Cascade
作者:Lewis B. Smith,Roly J. Armstrong,Daniel Matheau-Raven,Timothy J. Donohoe |发布日期:2020.2.5
摘要:Acceptorless Dehydrogenation Of The Diol Followed By A Redox-Neutral Cascade Process, Which Is Independent Of The Iridium Catalyst. Deuterium Labeling Studies Established That The Key Step Of This Cascade Involves A Novel Base-Mediated [1,5]-Hydride Shift. The Cyclohexenyl Ketone Products Could Readily Be Cleaved Under Mildly Acidic Conditions To Access A Range Of Valuable Substituted Cyclohexene Derivatives

合成参考文献


摘要:Hollmann, F., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 129.
摘要:Herter, S.; Turner, N. J., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 150.
摘要:Dornan, L. M.; Hughes, N. L.; Muldoon, M. J., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 546.
摘要:Casano, G.; Ouari, O., Science of Synthesis, (2021) , 59.
摘要:Parmeggiani, F.; Galman, J. L.; Montgomery, S. L.; Turner, N. J., Science of Synthesis, (2019) , 367.
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