CAS: 81445-44-5; (S)-2-(Benzyloxy)Propanal

该化合物是有机化合物,其特征是其手性中心,具有特定的立体化学特性.该化合物具有一个带有苯甲基苯丙氧组的丙烷基柱,有助于其反应和潜在应用有机合成.该苯基组的存在增强了其疏水特性,而甲酰胺功能组则使它成为各种化学反应(如核脑医学添加)的被动场所.2S)的命名表明该化合物可以显示不同的生物活动,这往往是与手性分子有关的情况.其溶性特征一般反映有机溶剂中的中溶性,而其再活性可以被合成途径所利用,特别是在形成更复杂的有机结构时.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

REACH注册C&L通报REACH预注册

上下游产品

CAS号54783-72-1 ethyl (S)-2-(be... | CAS号77287-11-7 (S)-2-(苄氧基)丙酸甲酯 | CAS号33106-64-8 (S)-1-苄氧基-2-丙醇 | CAS号1234714-02-3 (S)-2-(benzylox... | CAS号81927-55-1 2,2,2-三氯乙酰亚胺苄酯 | CAS号122151-32-0 (S)-2-(苄氧基)-1-(... | CAS号53346-05-7 2-phenylmethoxy... | CAS号100-39-0 溴化苄 | CAS号33106-64-8 (S)-1-苄氧基-2-丙醇 | CAS号112489-56-2 methyl (Z)-(S)-... | CAS号112489-57-3 甲基(2E,4S)-(-)-4... | CAS号170985-85-0 2-[(1S,2S)-1-乙基...

合成工艺路线路线简述

  • 33106-64-8 = 81445-44-5
    反应条件:1.1 Reagents: 1-Hydroxy-1,2-Benziodoxol-3(1H)-One 1-Oxide Solvents: Ethyl Acetate; 3.25 H,80 °C
    标题:Diastereoselective Addition Of Prochiral Nucleophilic Alkenes To α-Chiral N-Sulfonyl Imines
    作者:Gutierrez,David A.; Et Al
    参考文献:Organic Letters 日期:2022 卷标:24(5) 页码:1164-1168]

    33106-64-8 = 81445-44-5
    反应条件:1.1 Reagents: 1-Hydroxy-1,2-Benziodoxol-3(1H)-One 1-Oxide Solvents: Ethyl Acetate; Rt -> Reflux; 4 H,Reflux
    标题:Acyclic Stereocontrol In The Additions Of Nucleophilic Alkenes To α-Chiral N-Sulfonyl Imines
    作者:Moore,Lucas C.; Et Al
    参考文献:Chemistry - A European Journal 日期:2019 卷标:25(52) 页码:12214-12220]

    54783-72-1 = 81445-44-5
    反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane; 30 Min,-78 °C1.2 Reagents: Potassium Sodium Tartrate Solvents: Water; -78 °C -> Rt
    标题:Botcinolide/botcinin: Asymmetric Synthesis Of The Key Fragments
    作者:Ramirez-Fernandez,Jacinto; Et Al
    参考文献:Natural Product Communications 日期:2011 卷标:6(4) 页码:443-450]

    122151-33-1 = 81445-44-5
    反应条件:1.1 Reagents: Vitride Solvents: Tetrahydrofuran
    标题:An Improved Synthetic Method Of (S)-2-Alkoxypropanals From Ethyl (S)-Lactate
    作者:Kobayashi,Yuko; Et Al
    参考文献:Bulletin Of The Chemical Society Of Japan 日期:1989 卷标:62(9) 页码:3038-40]

    81927-55-1 + 687-47-8 = 81445-44-5
    反应条件:1.1 Reagents: Trifluoromethanesulfonic Acid Solvents: Dichloromethane,Cyclohexane1.2 Reagents: Diisobutylaluminum Hydride Solvents: Toluene,Tetrahydrofuran; -78 °C
    标题:Exploring The Solid-Phase Synthesis Of 3,4-Disubstituted β-Lactams: Scope And Limitations
    作者:Delpiccolo,Carina M. L.; Et Al
    参考文献:Journal Of Combinatorial Chemistry 日期:2005 卷标:7(2) 页码:331-344]

    81927-55-1 + 687-47-8 = 81445-44-5
    反应条件:1.1 Reagents: Trifluoromethanesulfonic Acid Solvents: Dichloromethane,Cyclohexane; Rt; 60 H,Rt2.1 Reagents: Diisobutylaluminum Hydride Solvents: Diethyl Ether,Hexane; -78 °C; 2 H,-78 °C
    标题:Volatile Lactones From Streptomycetes Arise Via The Antimycin Biosynthetic Pathway
    作者:Riclea,Ramona; Et Al
    参考文献:Chembiochem 日期:2012 卷标:13(11) 页码:1635-1644]

    77287-11-7 = 81445-44-5
    反应条件:1.1 Solvents: Dichloromethane; Rt -> -78 °C1.2 Reagents: Diisobutylaluminum Hydride Solvents: Toluene; -78 °C; 1 H,-78 °C; -78 °C
    标题:Stereoselective Synthesis Of Functionalized Triol Units By Sncl4 Promoted Allylation Of α-Benzyloxyaldehydes: Crucial Role Of The Stoichiometry Of The Lewis Acid
    作者:Dubost,Christophe; Et Al
    参考文献:Tetrahedron 日期:2004 卷标:60(35) 页码:7693-7704]

    77287-11-7 = 81445-44-5
    反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane,Hexane; -78 °C; 6 H,-78 °C1.2 Reagents: Potassium Sodium Tartrate Solvents: Water; -78 °C; -78 °C -> Rt; 1 H,Rt
    标题:Studies Towards The Total Synthesis Of Lactonamycin: Investigations Into Glycosidation Reactions
    作者:Rzepa,Paula Rocha
    参考文献:2008]

    = 81445-44-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
    标题:Palladium On Carbon
    作者:King,Anthony O.; Et Al
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001]

    687-47-8 = 81445-44-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 20 Min,0 °C1.2 0 °C -> Rt; 12 H,Rt1.3 Reagents: Water; Rt2.1 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane,Toluene; 25 Min,-78 °C; 1 H,-78 °C2.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 1 H,Rt
    标题:Direct Deprotonative Functionalization Of α,α-Difluoromethyl Ketones Using A Catalytic Organosuperbase
    作者:Messara,Amelia; Et Al
    参考文献:Angewandte Chemie 日期:2023 卷标:62(10)]

    3913-64-2 = 81445-44-5 [标题:Reaction Conditions
    标题:The First Total Synthesis Of Phomopsolidone A
    作者:Raju,Kasa Shiva; Et Al
    参考文献:Tetrahedron Letters 日期:2016 卷标:57(19) 页码:2109-2111]

    122151-32-0 = 81445-44-5
    反应条件:1.1 Reagents: Vitride Solvents: Toluene; 5 H,< Rt1.2 Reagents: Acetone
    标题:Stereoselective Grignard Additions To N-Formyl Hydrazone: A Concise Synthesis Of Noxafilr Side Chain And A Synthesis Of Noxafilr
    作者:Saksena,Anil K.; Et Al
    参考文献:Tetrahedron Letters 日期:2004 卷标:45(44) 页码:8249-8251]

    122151-32-0 = 81445-44-5
    反应条件:1.1 Reagents: Vitride Solvents: Toluene; 30 Min,-12 °C; 2.5 H,-13 - -10 °C1.2 Solvents: Acetone; 10 Min,-13 - -10 °C
    标题:Efficient Stereoselective Synthesis Of A Key Chiral Aldehyde Intermediate In The Synthesis Of Picolinamide Fungicides
    作者:Li,Fangzheng; Et Al
    参考文献:Organic Process Research & Development 日期:2019 卷标:23(10) 页码:2253-2260]

    122151-33-1 = 81445-44-5
    反应条件:1.1 Reagents: Vitride Solvents: Toluene,Tetrahydrofuran
    标题:(S)-Ethyl Lactate
    作者:Grabowski,Edward J. J.
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001 卷标:1 页码:1-4]

    81927-55-1 + 687-47-8 = 81445-44-5
    反应条件:1.1 Catalysts: Trifluoromethanesulfonic Acid1.2 Reagents: Diisobutylaluminum Hydride
    标题:Toward The Synthesis Of (+)-Peloruside A Via An Intramolecular Vinylogous Aldol Reaction
    作者:Gazaille,Jeffrey A.; Et Al
    参考文献:Organic Letters 日期:2012 卷标:14(1) 页码:178-181]

    = 81445-44-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
    标题:Palladium On Carbon
    作者:King,Anthony O.; Et Al
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001 卷标:1 页码:1-5]

    = 81445-44-5
    反应条件:1.1 Catalysts: Palladium Solvents: Methanol1.2 Reagents: Hydrogen
    标题:Synthesis Of The Four Stereoisomers Of 1,1,1-Trifluorobutane-2,3-Diol
    作者:Morelli,Carlo F.; Et Al
    参考文献:Organic Preparations And Procedures International 日期:2002 卷标:34(1) 页码:103-107]

    53346-03-5 = 81445-44-5
    反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Toluene; -50 °C; 2.5 H,-50 °C1.2 Reagents: Sodium Pyrosulfite Solvents: Water; -50 °C; -50 °C -> 20 °C1.3 Reagents: Sodium Hydroxide Solvents: Water; Ph 11,0 °C
    标题:Intermolecular 1,3-Dipolar Cycloadditions Of Azomethine Imines
    作者:Jones,Raymond C. F.; Et Al
    参考文献:Arkivoc (Gainesville 日期:2007 卷标:(5) 页码:152-166]

    105299-38-5 = 81445-44-5
    反应条件:1.1 Reagents: Boron Trifluoride,Mercuric Oxide Solvents: Diethyl Ether
    标题:Bakers' Yeast-Mediated Synthesis Of Protected α-Hydroxy Aldehydes
    作者:Guanti,Giuseppe; Et Al
    参考文献:Journal Of The Chemical Society 日期:1986 卷标:(2) 页码:138-40]

    687-47-8 = 81445-44-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide1.2 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane; -90 °C
    标题:Effect Of Substituents On The Ring-Closing Metathesis Reaction In The Synthesis Of Functionalized Nonanolactones
    作者:Ramirez-Fernandez,Jacinto; Et Al
    参考文献:Synlett 日期:2008 卷标:(3) 页码:339-342]

    687-47-8 = 81445-44-5
    反应条件:1.1 Reagents: Silver Oxide (Ag2O) Solvents: Diethyl Ether; 10 H,40 °C2.1 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane; 30 Min,-78 °C2.2 Reagents: Methanol
    标题:Luquilloamides,Cytotoxic Lipopeptides From A Puerto Rican Collection Of The Filamentous Marine Cyanobacterium Oscillatoria Sp.
    作者:Kim,Geum Jin; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2022 卷标:87(2) 页码:1043-1055]

    87604-55-5 = 81445-44-5
    反应条件:1.1 Catalysts: Lead Tetraacetate
    标题:On The Steric Course Of The Addition Of Some Organometallic Reagents To (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis Of Optically Active α-Benzyloxy Aldehydes,Alcohols,Carboxylic Acids And 1,2-Diols
    作者:Mulzer,Johann; Et Al
    参考文献:Tetrahedron Letters 日期:1983 卷标:24(28) 页码:2843-6]

    1234714-02-3 = 81445-44-5
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; -15 °C; 1 H,-15 °C1.2 Reagents: Water; Ph 7,0 °C1.3 Reagents: (-)-Camphorsulfonic Acid Solvents: Pentane; 1 H,Rt
    标题:Alkylation And Aldol Reactions Of Acyl Derivatives Of N-1-(1'-Naphthyl)Ethyl-O-Tert-Butylhydroxylamine: Asymmetric Synthesis Of α-Alkoxy-,α-Substituted-β-Alkoxy- And α,β-Dialkoxyaldehydes
    作者:Chernega,Alexander N.; Et Al
    参考文献:Tetrahedron 日期:2010 卷标:66(23) 页码:4167-4194]

    33106-64-8 = 81445-44-5
    反应条件:1.1 Reagents: 1-Hydroxy-1,2-Benziodoxol-3(1H)-One 1-Oxide Solvents: Ethyl Acetate; Rt -> 80 °C; 3.25 H,80 °C
    标题:Diastereoselective Addition Of Prochiral Nucleophilic Alkenes To α-Chiral N-Sulfonyl Imines
    作者:Gutierrez,David A.; Et Al
    参考文献:Chemrxiv 日期:2021 卷标:1 页码:1-6]

    54783-72-1 = 81445-44-5
    反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Diethyl Ether,Hexane; -78 °C; 1.5 H,-78 °C1.2 Reagents: Ammonium Chloride Solvents: Water
    标题:A Highly Stereoselective Ether Directed Palladium Catalyzed Aza-Claisen Rearrangement
    作者:Jamieson,Andrew G.; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2005 卷标:3(5) 页码:735-736]

    54783-72-1 = 81445-44-5
    反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Diethyl Ether,Hexane; 1.5 H,-78 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 0 °C
    标题:Synthesis Of (-)-(E,S)-3-(Benzyloxy)-1-Butenyl Phenyl Sulfone Via A Horner-Wadsworth-Emmons Reaction Of (-)-(S)-2-(Benzyloxy)Propanal
    作者:Enders,D.; Et Al
    参考文献:Organic Syntheses 日期:2002 卷标:78 页码:177-188
📜Methyl (S)-2-(Benzyloxy)Propanoate置于lithium Aluminium Tetrahydride体系中,用 四氢呋喃 作为反应溶剂,化学反应生成 (S)-2-苄氧基丙醛
参考文献:在立体选择性氮杂-Diels-Alder反应中使用未活化的亚氨基二烯基
标题:在立体选择性氮杂-Diels-Alder反应中使用未活化的亚氨基二烯基
摘要:本文介绍了非活化亚氨基二烯和环戊二烯的aza-Diels-Alder反应制备含氮自行车的方法.易于获得的原料,例如(S)-(-)-乳酸酯和1-氨基酸被用于制备具有高对映体过量的手性醛.用dess-Martin高碘烷改进的氧化程序合成了由l-丙氨酸衍生的邻苯二甲酰亚胺保护的醛14,该醛很难通过其他方法以高对映体的形式获得.还研究了不同的路易斯酸对aza-Diels-Alder反应的立体选择性的影响:发现结合使用bf 3 .et 2环加成反应中的o和tfa导致由14制备的亚胺完全外消旋化,而使用ticl 4可使环加成产物17A和17B具有高对映选择性(90%).
DOI:10.1016/j.Tetasy.2003.12.011

海关参考信息

专利信息


专利号:WO-2014097257-A1
优先权日:2012-12-21
标 题:A method of preparation of (1'r,3r,4r)-4-acetoxy-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone, a precursor for carbapenem antibiotics synthesis
发明人：GRZESZCZYK BARBARA; STECKO SEBASTIAN; FURMAN BARTÅ?OMIEJ; CHMIELEWSKI MAREK
权利人:INST CHEMII ORGANICZNEJ PAN
摘要:The subject of the present invention is a method of preparation of (1'R,3R,4R)-4-acetoxy-3-(1'- (tert-butyl-dimethylsilyloxy)ethyl)-2-azetidinone defined by the formula (1) which is a basic chiral building block in the synthesis of carbapenem antibiotics.

专利号:CN-108586280-A
优先权日:2017-12-29
标题 :Synthesis of N'-[(2S,3S)-2-(benzyloxy)pent-3-yl]formylhydrazide

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主要参考文献

参考标题:The First Total Synthesis Of Phomopsolidone A
作者:Kasa Shiva Raju,Atla Raju,Gowravaram Sabitha |发布日期:2016.5
摘要:The First Total Synthesis Of Phomopsolidone A Has Been Accomplished. The Key Features Of The Synthesis Include The Use Of A Stereoselective Grignard Addition Reaction, Still-Gennari And Acid Catalyzed Lactonization Reactions.

合成参考文献


摘要:Ramón, D. J.; Yus, M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 349.
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