CAS: 80-18-2; Methyl Benzenesulfonate

该化合物是含有化学公式C7H8O3S的有机磺酸酯,在有机合成中通常用作烷基剂,特别是用于将甲基组引入核生殖基质.由于全氟辛烷磺酸组的电子脱钩性质,该化合物具有高度的回活动性,有利于高效甲基反应.在受控条件下和与各种溶剂的兼容性使其在实验室和工业应用中成为多用途试剂.甲基苯基盐还被用于制备制药,农用化学品和特殊化学品.适当的处理至关重要,因为它对水分敏感,并可能具有刺激性.建议在一个冷干环境中储存,以保持其功效.

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合成工艺路线路线简述

  • 合成目标产物 Methyl Benzenesulfonate 主要起始原料 Dimethyl Sulfate And Benzene
  • 98-11-3 = 80-18-2
    反应条件:1.1 Solvents: Toluene; 5 Min,120 °C
    标题:Direct Synthesis Of Sulfonates Of Alcohol,Oxyma-O-Sulfonates And Oxime-O-Sulfonates Under Microwave Irradiation
    作者:Chandra,Jyoti; Et Al
    参考文献:Chemistryselect 日期:2017 卷标:2(27) 页码:8471-8477]

    1086226-01-8 = 80-18-2
    反应条件:1.1 Reagents: Hydrochloric Acid,Oxygen,1,4-Diazoniabicyclo[2.2.2]Octane,1,4-Disulfino-,Bis(Inner Salt) Catalysts: Cuprous Iodide Solvents: Dichloromethane,Water; 4 H,Rt
    标题:Visible-Light-Induced One-Pot Synthesis Of Sulfonic Esters Via Multicomponent Reaction Of Arylazo Sulfones And Alcohols
    作者:Luu,Truong Giang; Et Al
    参考文献:Rsc Advances 日期:2022 卷标:12(27) 页码:17499-17504]

    882-33-7 = 80-18-2
    反应条件:1.1 Reagents: Tetrabutylammonium Chloride,Oxygen Solvents: Methanol; 10 H,Rt
    标题:Electrochemical Synthesis Of Sulfinic Esters From Alcohols And Thiophenols
    作者:He,Yang; Et Al
    参考文献:Tetrahedron Letters 日期:2020 卷标:61(12)]

    1461-22-9 = 80-18-2 [标题:Reaction Conditions
    标题:The Reactions Of Trialkyl(Alkoxy)Stannane With Sulfonyl,Sulfinyl,And Sulfenyl Chlorides
    作者:Kozuka,Seizi; Et Al
    参考文献:Memoirs Of The Faculty Of Engineering 日期:1978 卷标:19 页码:181-3]

    3729-53-1 = 80-18-2 + 96088-61-8 + 3112-85-4
    反应条件:1.1 Reagents: Lead Dioxide Solvents: Dichloromethane2.1 -
    标题:Mesylhydroxylamines. Vi. Oxidation Of N-Mesylhydroxylamines - Vibrational Spectra And Crystal Structure Of 1,2-Dimesyl-1,2-Dimethoxyhydrazine
    作者:Brink,Klaus; Et Al
    参考文献:Chemische Berichte 日期:1985 卷标:118(2) 页码:564-73]

    142-45-0 + 150-76-5 = 80-18-2 + 37976-30-0 + 150-78-7 + 142207-57-6
    反应条件:1.1 Reagents: Sulfuric Acid Solvents: Benzene
    标题:Preparation And Photolysis Of Diaryl Esters Of Acetylenedicarboxylic Acid
    作者:Alvaro,Mercedes; Et Al
    参考文献:Tetrahedron 日期:1992 卷标:48(16) 页码:3437-44]

    37976-30-0 = 80-18-2 + 37976-30-0 + 150-78-7 + 142207-57-6
    反应条件:1.1 Solvents: Benzene2.1 Reagents: Sulfuric Acid Solvents: Benzene
    标题:Preparation And Photolysis Of Diaryl Esters Of Acetylenedicarboxylic Acid
    作者:Alvaro,Mercedes; Et Al
    参考文献:Tetrahedron 日期:1992 卷标:48(16) 页码:3437-44]

    1067-52-3 = 80-18-2 [标题:Reaction Conditions
    标题:The Reactions Of Trialkyl(Alkoxy)Stannane With Sulfonyl,Sulfinyl,And Sulfenyl Chlorides
    作者:Kozuka,Seizi; Et Al
    参考文献:Memoirs Of The Faculty Of Engineering 日期:1978 卷标:19 页码:181-3]

    = 80-18-2
    反应条件:1.1 Catalysts: Cesium Fluoride (Celite-Supported); 1.5 H,50 °C
    标题:Csf-Celite As An Efficient Heterogeneous Catalyst For Sulfonylation And Desulfonylation Of Heteroatoms
    作者:Tamaddon,Fatemeh; Et Al
    参考文献:Catalysis Communications 日期:2011 卷标:12(15) 页码:1477-1482]

    14874-70-5 + 2684-02-8 = 80-18-2
    反应条件:1.1 Reagents: Trifluoroacetic Acid,Oxygen,1,4-Diazoniabicyclo[2.2.2]Octane,1,4-Disulfino-,Bis(Inner Salt) Catalysts: Copper Bromide (Cubr2) Solvents: Dichloromethane; 12 H,Rt
    标题:Copper-Catalyzed Multicomponent Reaction Of Dabco.(So2)2,Alcohols,And Aryl Diazoniums For The Synthesis Of Sulfonic Esters
    作者:Wang,Yang; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2018 卷标:83(8) 页码:4674-4680]

    = 80-18-2
    反应条件:1.1 8 H,95 °C
    标题:A Simple Method For The Synthesis Of Sulfonic Esters
    作者:Bhatthula,Bharath Kumar Goud; Et Al
    参考文献:Synthetic Communications 日期:2020 卷标:50(20) 页码:3133-3148]

    882-33-7 = 80-18-2
    反应条件:1.1 Reagents: Tetrabutylammonium Chloride,Oxygen Solvents: Methanol; 10 H,Rt
    标题:Electrochemical Synthesis Of Sulfinic Esters From Alcohols And Thiophenols
    作者:He,Yang; Et Al
    参考文献:Chemrxiv 日期:2019 卷标:1 页码:1-13]

    18883-66-4 + 98-11-3 = 80-18-2
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 2 Min,Rt1.2 4 H,Rt
    标题:O-Methylation Of Carboxylic Acids With Streptozotocin
    作者:Zeng,Li-Yan; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2022 卷标:20(26) 页码:5230-5233]

    = 80-18-2
    反应条件:1.1 Reagents: Nitrogen Oxide (N2O4) Solvents: Methanol
    标题:Multistep Oxidations Of The Unsymmetrical Disulfide And Thiolsulfinates: New Evidence For The Formation Of The Thionitrite And The Sulfinyl Derivatives As The Intermediates
    作者:Oae,Shigeru; Et Al
    参考文献:Chemistry Letters 日期:1978 卷标:(3) 页码:279-80]

    96088-58-3 = 80-18-2 + 96088-61-8 + 3112-85-4 [标题:Reaction Conditions
    标题:Mesylhydroxylamines. Vi. Oxidation Of N-Mesylhydroxylamines - Vibrational Spectra And Crystal Structure Of 1,2-Dimesyl-1,2-Dimethoxyhydrazine
    作者:Brink,Klaus; Et Al
    参考文献:Chemische Berichte 日期:1985 卷标:118(2) 页码:564-73
苯磺酸置于tetrabutylammonium Tetrafluoroborate,三乙胺,N,N'-羰基二咪唑体系中,用 乙腈 作为反应溶剂,化学反应 16.5H,反应生成 苯磺酸甲酯
参考文献:磺酰肼电化学合成亚磺酸酯和磺酸酯
标题:磺酰肼电化学合成亚磺酸酯和磺酸酯
摘要:开发了一种由磺酰肼合成亚磺酸酯和磺酸酯的电化学合成方法.在dmf溶剂中,5 Ma恒电流下,用原甲酸三烷基酯处理磺酰肼,然后优化反应条件,合成烷基亚磺酸酯.相反,当反应在烷基醇溶剂中以15Ma的恒定电流进行时,仅获得烷基磺酸酯.各种取代的芳基磺酰肼提供了中等至非常好产率的所需亚磺酸酯和磺酸酯.机理研究表明,磺酰基自由基是通过电化学氧化形成的,并且它们与烷基自由基或烷氧基自由基反应反应生成各自的酯产物.
DOI:10.1039/d4Ob00215F

海关参考信息

专利信息


专利号:US-8791287-B2
优先权日:2010-07-02
标 题:Process for the synthesis of tapentadol and intermediates thereof
发明人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA
权利人:MOTTA GIUSEPPE; VERGANI DOMENICO; BERTOLINI GIORGIO; LANDONI NICOLA; EUTICALS SPA
摘要:The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. n A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention. n Still another object of the invention is represented by the crystalline forms I and II of the tapentadol free base. n A further object of the present invention is the mixture of the crystalline forms I and II of the tapentadol free base.

专利号:US-9085538-B2
优先权日:2010-07-26
标题:Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof
发明人:CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO
权利人:CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO; LEK PHARMACEUTICALS
摘要:The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

专利号:US-9597327-B2
优先权日:2005-05-25
标 题:Synthesis of (R)-N-methylnaltrexone
发明人:DOSHAN HAROLD D; PEREZ JULIO
权利人:PROGENICS PHARM INC
摘要:This invention relates to stereoselective synthesis of R-MNTX and intermediates thereof, pharmaceutical preparations comprising R-MNTX or intermediates thereof and methods for their use.

专利号:US-9908846-B2
优先权日:2014-02-21
标题:Composition, synthesis, and use of new arylsulfonyl isonitriles
发明人:FLEMING FRASER FERGUSSON; LUJAN MONTELONGO JESUS ARMANDO
权利人:DUQUESNE UNIV OF THE HOLY GHOST; UNIV HOLY GHOST DUQUESNE
摘要:This invention relates to novel isonitriles, including arylsulfonyl isonitriles, and methods for their synthesis. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.

专利号:US-8133707-B2
优先权日:2006-01-17
标 题 :Methods of preparing activated polymers having alpha nitrogen groups
发明人:ZHAO HONG; WU DECHUN
权利人:ZHAO HONG; WU DECHUN; ENZON PHARMACEUTICALS INC
摘要:Methods for preparing substantially non-antigenic polymers having lone electron pair-containing moieties in high purity are disclosed. The polymers are useful as intermediates for synthesis of amine-based polymers and in the formation of activated polymers for conjugation with nucleophiles. Conjugates and methods of preparation and treatment with the conjugates are also disclosed. The resultant polymer-amines are of sufficient purity so that expensive and time consuming purification steps required for pharmaceutical grade polymers are avoided.

专利号:US-4697001-A
优先权日:1984-09-04
标题:Chemical synthesis of conducting polypyrrole
发明人:WALKER JOHN A; WITUCKI EDWARD F; WARREN LESLIE F
权利人:ROCKWELL INTERNATIONAL CORP
摘要:Production of electrically conductive polypyrrole of enhanced stability by treating a liquid pyrrole with a solution of a strong oxidant, capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing the pyrrole by such strong oxidant in the presence of a relatively large organic dopant anion, and precipitating a conductive polypyrrole. The strong oxidant, e.g., Fe3+ ion, and dopant anion, which can be an alkyl or aryl sulfonate, e.g., methylbenzenesulfonate, or a perfluorinated carboxylate, e.g., trifluoroacetate, anion, can be derived from a single compound, e.g., the anion serving as dopant for the polypyrrole.
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合成参考文献


摘要:Hall, D. G.; Zheng, H., Science of Synthesis Knowledge Updates, (2011) 4, 73.
摘要:Ros, A.; Fernández, R.; Lassaletta, J. M., Science of Synthesis: Catalytic Transformations via CH Activation, (2015) 2, 417.
摘要:Yoshida, H., Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis, (2019) 1, 57.
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