DMF-DMA CAS 4637-24-5 N, N-Dimethylformamide Dimethyl Acetal Purity>99.0% (GC) Tita Gbona Ile-iṣẹ

Niwọn igba ti Meenvin ṣe ijabọ igbaradi ti DMF-DMA (N, N-Dimethylformamide Dimethyl Acetal) ni ọdun 1956, DMF-DMA ti di reagent nigbagbogbo ti a lo ninu iṣelọpọ Organic.
DMF-DMA jẹ lilo pupọ ni ikole ti awọn oruka heterocyclic marun tabi mẹfa ti o ni ọmọ ẹgbẹ ninu iṣesi pipade oruka.DMF-DMA ni iṣesi kekere ati ikore giga, pataki fun awọn agbo ogun resistance giga.
Eto gbogbogbo ti awọn agbo ogun acetal amide jẹ bi atẹle:
Lilo pupọ julọ ni DMF-DMA ati DMF-DEA, amide acetal jẹ irọrun hydrolyzed, le jẹ esterified, amidine, alkylation ati awọn aati cyclization.
Atọmu erogba aringbungbun ti DMF-DMA ni asopọ pẹlu awọn heteroatoms mẹta pẹlu itanna eletiriki nla, eyiti o jẹ ki o ni iṣẹ elekitirofiki to lagbara.Labẹ iṣẹ ti acid, ẹgbẹ alkoxy rọrun lati lọ kuro, ati awọn ions rere pẹlu iṣẹ ṣiṣe elekitiroli ti o lagbara ni a gba.Ihuwasi ti DMF-DMA ni akọkọ ni iṣesi methylation ati iṣesi iṣelọpọ.
"Ọkan-erogba Syntheson" ti DMF-DMA
Ninu iṣesi pipade lupu ti o kan DMF-DMA, atomu erogba kan ṣoṣo ninu ọja naa ni igbagbogbo pese nipasẹ DMF-DMA, nitorinaa DMF-DMA ni a le gba bi iṣelọpọ erogba.
Idahun esterification DMF-DMA
DMF-DMA esterification jẹ ki ọpọlọpọ awọn acids carboxylic lati ṣe ipilẹṣẹ C1-20 alkyl tabi awọn esters aryl ni irọrun, ati awọn ọja nipasẹ awọn ọja le ni irọrun niya nipasẹ distillation.
Adipic acid ati DMF-DMA ni a sọ di iwọn 80 fun wakati meji.Amide acetal jẹ yiyan ti o dara julọ fun didasilẹ diẹ ninu awọn acids carboxylic pẹlu idiwọ sita tabi iduroṣinṣin ti ko dara.
Ifesi ti DMF-DMA amidination ati aabo ti awọn amines akọkọ
Amide acetals le fesi kii ṣe pẹlu awọn amines akọkọ nikan, ṣugbọn pẹlu awọn amides, carbamates, sulfonamides lati ṣe awọn ifunmọ hydrocarbon.
Bii: 2, 4-dimethyl aniline ati DMF-DMA ni awọn iwọn 80 le yarayara yọ kẹmika kẹmika lati dagba awọn agbo ogun dimethamidine.
DMF-DMA tun le ṣee lo bi ẹgbẹ aabo aabo amine akọkọ, ẹgbẹ aabo aabo akọkọ (2 NH gbogbo aabo) boya ọpọlọpọ eniyan ronu ti phthalyl, oruka pyrrole, Double Boc, PMB meji, ati bẹbẹ lọ, ṣugbọn aabo DMF-DMA ti akọkọ amine, ni awọn igba miiran jẹ tun gan wulo Idaabobo eni, pa Idaabobo nikan nilo TFA a illa.
Idaabobo Amino - Ifihan ipilẹ aabo ti o wọpọ 13, iriri yiyan ipilẹ aabo, iwọn lilo, awọn ipo ifihan, awọn ipo yiyọkuro akojọpọ pinpin
DMF-DMA fesi pẹlu methyl lọwọ ati awọn ẹgbẹ methylene lati dagba erogba-erogba meji ìde
Phenylmethylation ti DMF-DMA
Awọn aati heterocyclic yellow ni DMF-DMA
Amide acetal gẹgẹbi oluranlọwọ erogba ẹyọkan ni a le lo lati ṣajọpọ ọpọlọpọ awọn agbo ogun eka ati awọn nkan adayeba biomimetic.Pẹlu amide acetals le ti wa ni sise: 1,2.4 triazole, 1.2, 4 triazolone, aminoheterocyclic awọn itọsẹ, pyrimidine, pyrimidine, indoles, pyridine, quinoline, thiazole, oxazolone, isooxazole, 1.2, 4-triazone, pyrazine miiran, pyrazine jara, pyrazine, ti awọn itọsẹ heterocyclic amonia, tun le jẹ atẹgun ti iṣelọpọ, awọn agbo ogun heterocyclic imi-ọjọ.
Ni ibamu si iru iṣesi kemikali, ohun elo ti amide acetal ni iṣelọpọ heterocyclic yellow le ti pin si awọn aaye mẹta wọnyi.
(1): amide acetal ati amine, amide, ifaseyin lipid carbamate, ṣe agbekalẹ ọpọlọpọ awọn oruka heterocyclic.
Amidoacetal ati amine lenu si agbedemeji formamidine, ati lẹhinna intramolecular nucleophilic oruka lenu lati ṣe agbekalẹ ọpọlọpọ awọn heterocycles, tabi formamidine ati hydrazine, hydroxylamine, l, 2, ọkan tabi meji alkyl halides ti o ni awọn ẹgbẹ meji ti nṣiṣe lọwọ ti awọn agbo ogun pẹlu pq erogba gigun, ati lẹhinna oruka intramolecular .
Iṣagbepọ ti awọn agbo ogun heterocyclic nipasẹ iṣesi ti awọn acetals amide ati awọn amides, gẹgẹbi iṣelọpọ ti l, 2,4 monotriazole awọn itọsẹ.Ni akọkọ, acetal ṣe atunṣe pẹlu amide lati ṣe N, N 'tritradil, ati lẹhinna awọn oruka pẹlu phenylhydrazine lati dagba l, 2,4 awọn itọsẹ monotriazole
Amide acetals fesi pẹlu carbamic acid tabi acetate lati ṣe awọn oruka heterocyclic ti o ni chlorine ninu.Agbedemeji dictive ti a ṣẹda nipasẹ iṣesi ti acetal amide pẹlu ester aminoethyl: nn-dimethyl-n 'alkyl-carboxymethyl formamidine, eyiti o ṣe atunṣe pẹlu hydrazine tabi aropo hydrazine.Fun apẹẹrẹ, fun igbaradi ti 1,2,4 triazinone-6, idogba naa han ni isalẹ.Ti o ba fesi pẹlu ọna kika nitro o gba 1,2,4 triazolone-5.
Ilana ifaseyin fun dida 1,2,4 triazolone-5
Awọn akopọ ti 1.2.4-triazolidin-5 jẹ awọn igbesẹ meji.Ni akọkọ, ethyl carbamate ati DMF diformaldehyde acetals ṣe agbedemeji Nn-dimethyl-n-ethoxy-formamidine.Keji, awọn amino ẹgbẹ on phenylhydrazine deattacks awọn erogba lori formamidine, eyi ti o padanu -N (CH3).Lẹhinna amonia ti o wa lori oruka benzene ti o sunmọ phenylhydrazine kọlu erogba lori ẹgbẹ erogba, ti o ṣẹda anion atẹgun, ati pe awọn elekitironi nikan ti o wa lori atẹgun wa silẹ, padanu ẹgbẹ ethoxy, o si ṣe 1.2, 4-triazolone-5.
(II) Igbaradi ti awọn agbo ogun heterocyclic nipasẹ iṣesi ti amide acetal ati amide
Eyi ni ọna ti a royin julọ ti aimọ kolaginni ni awọn ọdun aipẹ.Iṣe ti acetal amide jẹ deede si Grignard reagent, ṣugbọn ipo iṣesi ti amide acetal jẹ rọrun ati ìwọnba.
Amide acetal ni awọn ẹgbẹ meji ti nṣiṣe lọwọ, ifaseyin giga, ati methyl ti nṣiṣe lọwọ, iṣesi methylene lati dagba awọn agbedemeji amidine, le jẹ ifasi siwaju sii, pipade oruka, ati Grignard reagent ati ifasẹ methylene, gigun gigun pq erogba, ko le jẹ ifasi siwaju sii.Fun apẹẹrẹ, iṣelọpọ ti awọn itọsẹ furanochroone.
(3): amide acetal ati hydroxyl, sulfhydryl yellow lenu lati ṣe ina atẹgun, sulfur heterocyclic agbo
Iṣọkan ti o wa loke ti furohutanone jẹ apẹẹrẹ ti o dara fun iran acetal ti awọn itọsẹ enamine ati ẹgbẹ hydroxyl nipa yiya sọtọ ọpa endolateral, ti o mu ki heteramine ti o ni atẹgun:.Apeere miiran: catechol ati DMF -- DMA ṣe awọn oruka ti o ni atẹgun ni iwaju dichloromethane.
Idahun ti DMF - DMA ati o-mercaptoaniline le ṣe agbejade oruka heterocyclic ti o ni imi-ọjọ imi-ọjọ, agbekalẹ ifaseyin jẹ bi atẹle.
Iwadi ọran ti iṣe pipade oruka DMF-DMA ati iṣesi ti ara ẹni
(1) Batcho-Leimgruber indole kolaginni
Igbaradi ti awọn orisirisi awọn itọsẹ Vindol lati o-nitrotoluene.
Ilana ifaseyin
Ni akọkọ, dimethylformamide dimethylacetal, awọn ions odi ti ẹgbẹ methoxy fi silẹ lati ṣe agbedemeji ifaseyin diẹ sii.O ti kọlu nipasẹ awọn carboanions ti o ṣẹda nipasẹ deprotonation ti o-nitrotoluene methyl hydrogen ati pe o padanu methanol lati gba enylamine ti a mẹnuba loke.Ọja ti igbese yii, enamine, dabi alkene kan pẹlu yiyọ elekitironi ati awọn aropo itọrẹ elekitironi ti a so ni ẹgbẹ mejeeji (Titari-pull olefin jẹ pola ti o lagbara ati nigbagbogbo pupa dudu nitori ibiti isunmọ nla ti o wa ninu moleku naa. Ni igbesẹ keji. ti iṣesi, ẹgbẹ nitro ti dinku si ẹgbẹ amino kan, atẹle nipa gigun kẹkẹ ati imukuro lati gba ọja ikẹhin.
(2) Awọn aworan akojọpọ ti awọn itọsẹ pyridine
(3) Akopọ ti awọn itọsẹ pyrazole