DMF-DMA CAS 4637-24-5 N, N-Dimethylformamide Dimethyl Acetal Purity > 99.0% (GC) Hoobkas kub muag

Txij li thaum Meenvin tau tshaj tawm txog kev npaj ntawm DMF-DMA (N, N-Dimethylformamide Dimethyl Acetal) hauv xyoo 1956, DMF-DMA tau dhau los ua cov tshuaj reagent feem ntau siv hauv cov organic synthesis.
DMF-DMA yog dav siv nyob rau hauv kev tsim kho ntawm tsib los yog rau lub koom haum heterocyclic rings nyob rau hauv lub nplhaib kaw cov tshuaj tiv thaiv.DMF-DMA muaj cov tshuaj tiv thaiv me me thiab cov txiaj ntsig siab, tshwj xeeb tshaj yog rau cov tshuaj tiv thaiv siab.
Cov qauv dav dav ntawm amide acetal compounds yog raws li nram no:
Feem ntau siv yog DMF-DMA thiab DMF-DEA, amide acetal yog yooj yim hydrolyzed, yuav ua tau esterified, amidine, alkylation thiab cyclization cov tshuaj tiv thaiv.
Lub hauv paus carbon atom ntawm DMF-DMA yog txuas nrog peb heteroatoms nrog loj electronegative, uas ua rau nws muaj zog electrophilic kev ua si.Nyob rau hauv qhov kev txiav txim ntawm cov kua qaub, pawg alkoxy yog yooj yim tawm, thiab cov ions zoo nrog cov kev ua haujlwm electrophilic muaj zog.Cov tshuaj tiv thaiv ntawm DMF-DMA feem ntau muaj cov tshuaj tiv thaiv methylation thiab tsim cov tshuaj tiv thaiv.
"One-carbon Syntheson" ntawm DMF-DMA
Nyob rau hauv lub voj kaw cov tshuaj tiv thaiv nrog DMF-DMA, tsuas yog ib qho carbon atom hauv cov khoom feem ntau yog muab los ntawm DMF-DMA, yog li DMF-DMA tuaj yeem suav tias yog carbon syntheson.
DMF-DMA esterification cov tshuaj tiv thaiv
DMF-DMA esterification ua rau muaj ntau yam carboxylic acids kom yooj yim tsim C1-20 alkyl los yog aryl esters, thiab byproducts tau yooj yim sib cais los ntawm distillation.
Adipic acid thiab DMF-DMA tau esterified ntawm 80 degrees rau ob teev.Amide acetal yog qhov kev xaiv zoo tshaj plaws rau esterification ntawm qee cov carboxylic acids nrog steric hindrance los yog tsis zoo stability.
Cov tshuaj tiv thaiv ntawm DMF-DMA amidination thiab tiv thaiv thawj amines
Amide acetals tuaj yeem ua tsis tau tsuas yog nrog thawj amines, tab sis kuj nrog amides, carbamates, sulfonamides los tsim hydrocarbon bonds.
Xws li: 2, 4-dimethyl aniline thiab DMF-DMA ntawm 80 degrees tuaj yeem tshem tawm methanol sai sai los tsim cov tshuaj dimethamidine.
DMF-DMA kuj tseem siv tau los ua thawj pawg amine tiv thaiv, thawj pawg amine tiv thaiv (2 NH tag nrho cov kev tiv thaiv) tej zaum cov neeg feem coob xav txog phthalyl, pyrrole nplhaib, ob chav Boc, ob chav PMB, thiab lwm yam, tab sis DMF-DMA kev tiv thaiv thawj. amine, qee zaum kuj tseem muaj txiaj ntsig zoo tiv thaiv, tawm kev tiv thaiv tsuas yog xav tau TFA sib xyaw.
Kev tiv thaiv Amino - 13 hom kev tiv thaiv hauv paus kev taw qhia, kev tiv thaiv lub hauv paus kev xaiv, ntau yam ntawm kev siv, kev taw qhia cov xwm txheej, tshem tawm cov ntsiab lus sib qhia
DMF-DMA reacts nrog active methyl thiab methylene pawg los tsim carbon-carbon ob daim ntawv cog lus
Phenylmethylation ntawm DMF-DMA
Heterocyclic compound reactions hauv DMF-DMA
Amide acetal raws li ib tus neeg pub dawb tuaj yeem siv los ua ke ntau yam sib xyaw ua ke thiab biomimetic ntuj tshuaj.Nrog amide acetals tuaj yeem ua ke: 1,2.4 triazole, 1.2, 4 triazolone, aminoheterocyclic derivatives, pyrimidine, pyrimidine, indoles, pyridine, quinoline, thiazole, oxazolone, isooxazole, 1.2, pyranine, pyrazine thiab series pyrazine. ntawm ammonia heterocyclic derivatives, kuj tuaj yeem ua rau cov pa oxygen, sulfur heterocyclic compounds.
Raws li hom tshuaj tiv thaiv, daim ntawv thov ntawm amide acetal hauv heterocyclic compound synthesis tuaj yeem muab faib ua peb yam hauv qab no.
(1): amide acetal thiab amine, amide, carbamate lipid cov tshuaj tiv thaiv, tsim ntau hom heterocyclic rings
Amidoacetal thiab amine cov tshuaj tiv thaiv rau formamidine nruab nrab, thiab tom qab ntawd intramolecular nucleophilic nplhaib cov tshuaj tiv thaiv los tsim ntau yam heterocycles, los yog formamidine thiab hydrazine, hydroxylamine, l, 2, ib lossis ob lub alkyl halides uas muaj ob pawg ntawm cov khoom sib txuas ntxiv rau cov roj carbon ntev, thiab tom qab ntawd intramolecular nplhaib. .
Synthesis ntawm heterocyclic tebchaw los ntawm cov tshuaj tiv thaiv ntawm amide acetals thiab amides, xws li cov synthesis ntawm l, 2,4 monotriazole derivatives.Ua ntej, cov acetal reacts nrog amide rau daim ntawv N, N 'tritradil, thiab ces rings nrog phenylhydrazine los ua l, 2,4 monotriazole derivatives
Amide acetals hnov ​​​​mob nrog carbamic acid los yog acetate los tsim cov chlorine-muaj heterocyclic rings.Lub diactive intermediate tsim los ntawm cov tshuaj tiv thaiv ntawm ib qho amide acetal nrog ib qho aminoethyl ester: nn-dimethyl-n 'alkyl-carboxymethyl formamidine, uas reacts nrog hydrazine los yog hloov hydrazine.Piv txwv li, rau kev npaj ntawm 1,2,4 triazinone-6, qhov sib npaug yog qhia hauv qab no.Yog tias koj ua rau nws nrog nitro-formate koj tau txais 1,2,4 triazolone-5.
Cov tshuaj tiv thaiv mechanism rau kev tsim ntawm 1,2,4 triazolone-5
Cov muaj pes tsawg leeg ntawm 1.2.4- triazolidin-5 yog ob kauj ruam.Ua ntej, ethyl carbamate thiab DMF diformaldehyde acetals tsim cov nruab nrab Nn-dimethyl-n-ethoxy-formamidine.Thib ob, pawg amino ntawm phenylhydrazine deattacks cov pa roj carbon monoxide ntawm formamidine, uas poob -N (CH3).Tom qab ntawd cov ammonia ntawm lub nplhaib benzene nyob ze ntawm phenylhydrazine tawm tsam cov pa roj carbon monoxide ntawm cov pa roj carbon monoxide, tsim cov pa oxygen anion, thiab ob leeg electrons ntawm cov pa tawm los, poob pawg ethoxy, thiab tsim 1.2, 4-triazolone-5.
(II) Kev npaj cov tshuaj heterocyclic los ntawm cov tshuaj tiv thaiv ntawm amide acetal thiab amide
Qhov no yog txoj kev qhia tshaj plaws ntawm kev sib xyaw impurity nyob rau hauv kaum xyoo tsis ntev los no.Qhov kev txiav txim ntawm amide acetal yog sib npaug rau Grignard reagent, tab sis cov tshuaj tiv thaiv ntawm amide acetal yog qhov yooj yim thiab me me.
Amide acetal muaj ob pawg active, siab reactivity, thiab active methyl, methylene cov tshuaj tiv thaiv los tsim amidine intermediates, yuav ua tau ntxiv cov tshuaj tiv thaiv, lub nplhaib kaw, thiab Grignard reagent thiab methylene cov tshuaj tiv thaiv, tsuas lengthening cov pa roj carbon saw, tsis tuaj yeem tiv thaiv ntxiv.Piv txwv li, synthesis ntawm furanochroone derivatives.
(3): amide acetal thiab hydroxyl, sulfhydryl compound cov tshuaj tiv thaiv los tsim cov pa oxygen, sulfur heterocyclic compounds
Cov synthesis saum toj no ntawm furohutanone yog ib qho piv txwv zoo ntawm acetal tiam ntawm enamine derivatives thiab hydroxyl pawg los ntawm kev sib cais ntawm endolateral ncej, uas ua rau oxy-muaj heteramine:.Lwm qhov piv txwv: catechol thiab DMF - DMA tsim cov nplhaib uas muaj oxygen nyob rau hauv lub xub ntiag ntawm dichloromethane.
Cov tshuaj tiv thaiv ntawm DMF - DMA thiab o-mercaptoaniline tuaj yeem tsim cov sulfur-muaj heterocyclic nplhaib, cov tshuaj tiv thaiv mis yog raws li nram no
Cov ntaub ntawv kawm ntawm DMF-DMA lub nplhaib kaw cov tshuaj tiv thaiv thiab cov tshuaj tiv thaiv tus kheej
(1) Batcho-Leimgruber indole synthesis
Kev npaj ntawm ntau yam Vindol derivatives los ntawm o-nitrotoluene.
Cov tshuaj tiv thaiv mechanism
Ua ntej ntawm tag nrho cov, dimethylformamide dimethylacetal, qhov tsis zoo ions ntawm pawg methoxy tawm mus ua ib qho kev cuam tshuam ntau dua.Nws raug tawm tsam los ntawm carboanions tsim los ntawm deprotonation ntawm o-nitrotoluene methyl hydrogen thiab poob cov methanol kom tau txais cov enylamine saum toj no.Cov khoom ntawm cov kauj ruam no, enamine, zoo ib yam li alkene nrog electron rho tawm thiab electron-dawb hloov pauv txuas rau ntawm ob sab (Push-rub olefin yog qhov muaj zog polar thiab feem ntau tsaus liab vim qhov loj conjugation ntau yam hauv cov molecule. ntawm cov tshuaj tiv thaiv, cov pab pawg nitro raug txo mus rau ib pawg amino, ua raws li cyclization thiab tshem tawm kom tau txais cov khoom kawg.
(2) Composite duab ntawm pyridine derivatives
(3) Synthesis ntawm pyrazole derivatives