Tom ntej: Dibenzyl Azodicarboxylate CAS 2449-05-0

Dibenzyl azodicarboxylate hmoov, Molecular formula C16H14N2O4, CAS 2449-05-0. Nws zoo nkaus li daj rau txiv kab ntxwv crystalline hmoov ntawm chav tsev kub thiab siab. Nws yog ib hom kev sib xyaw uas muaj ob qho tib si azo thiab carboxyl functional pawg. Vim nws cov khoom siv hluav taws xob tshwj xeeb thiab cov qauv tsim, azodicarboxylic acid dialkyl esters tau dav siv los ua cov khoom siv ntau yam hauv cov organic synthesis, tshwj xeeb tshaj yog nyob rau hauv MChemical bookitsunobu cov tshuaj, ammonification ntawm carbonyl tebchaw, ammonification ntawm unsaturated hydrocarbons, thiab synthesis ntawm heterocyclic compounds. Tsis tas li ntawd, azodicarboxylic acid esters kuj tuaj yeem ua oxidants rau dehydrogenation oxidation cov tshuaj tiv thaiv ntawm cawv thiab amines. Kev siv dav hauv Mitsunobu cov tshuaj tiv thaiv thiab carboxyl functionalization cov tshuaj tiv thaiv, nws tuaj yeem siv rau kev hloov kho thiab derivatization ntawm cov tshuaj molecules, bioactive molecules, thiab tshuaj tua kab molecules.

DBAD muaj ntau yam kev siv, suav nrog ntau qhov chaw xws li organic synthesis, tshuaj chemistry, cov ntaub ntawv science, qab zib chemistry, thiab asymmetric catalysis. Nws tus nqi tseem ceeb nyob rau hauv nws qhov tshwj xeeb reactivity raws li ib tug bifunctional reagent.

Organic synthesis: ib tug paradigm ntawm multifunctional cov tshuaj tiv thaiv reagents

 

DBAD plays lub luag hauj lwm ntawm "molecular connector" nyob rau hauv cov organic synthesis, thiab nws cov azo thiab carboxyl ester pawg tuaj yeem koom nrog ntau yam kev cuam tshuam tseem ceeb kom ua tiav kev tsim cov carbon carbon thiab carbon nitrogen bonds, nrog rau kev hloov kho ntawm cov pob txha molecular.

1. Mitsunobu tshuaj tiv thaiv
DBAD yog lub hauv paus reagent ntawm Mitsunobu cov tshuaj tiv thaiv, uas hloov cov cawv hydroxyl pawg mus rau hauv cov pab pawg zoo (xws li phosphonates) los ntawm kev sib koom ua ke ntawm triphenylphosphine (PPh3) thiab DBAD, yog li ua tiav kev sib txuas ntawm cov cawv nrog nucleophilic reagents xws li carboxylic acid, carboxylic acid, thiab lwm yam.

 

Piv txwv li, nyob rau hauv cov synthesis ntawm chiral tshuaj intermediates, cov tshuaj tiv thaiv Mitsunobu tuaj yeem tsim cov qauv tseem ceeb xws li - amino alcohols thiab - hydroxy acids, nrog cov txiaj ntsig siab thiab zoo heev stereoselectivity.

2. Carboxyl functionalization cov tshuaj tiv thaiv
DBAD tuaj yeem hloov cov carboxylic acids rau hauv ntau cov tshuaj sib xyaw ua ke (xws li benzyloxycarbonyl anhydride) rau kev hloov pauv ntawm cov amino acids, peptides, thiab nucleosides. Piv txwv li, nyob rau hauv peptide synthesis, DBAD ua hauj lwm pab raws li ib tug tiv thaiv pab pawg neeg reagent uas muaj peev xwm xaiv los tiv thaiv cov amino los yog carboxyl pawg, tsis txhob muaj kev phiv thiab txhim kho synthesis efficiency.

 

3. [4+2] cycloaddition tshuaj tiv thaiv
DBAD tuaj yeem raug [4+2] cycloaddition cov tshuaj tiv thaiv nrog cov carbohydrate derivatives (xws li glycerol) los tsim 2-aminoglycoside tebchaw. Hom tshuaj tiv thaiv no yog qhov tseem ceeb hauv glycochemistry thiab tuaj yeem siv los ua ke bioactive glycoconjugates, xws li tshuaj tua kab mob thiab tshuaj tua kab mob.

4. Asymmetric series ntxiv cyclization cov tshuaj tiv thaiv
Nyob rau hauv catalysis ntawm tooj liab (Cu) los yog palladium (Pd), DBAD tuaj yeem koom rau hauv asymmetric tandem ntxiv cyclization cov tshuaj tiv thaiv ntawm 2- (2 ', 3' - dienyl) - - ketoesters nrog cov organic halides, txhim kho optically active pyrazole derivatives. Cov tebchaw no muaj peev xwm siv tau hauv tshuaj chemistry, xws li enzyme inhibitors lossis receptor ligands.

Medicinal Chemistry: Ib Lub Cuab Yeej Tseem Ceeb rau Kev Hloov Tshuaj Molecular

 

Daim ntawv thov ntawm DBAD hauv kev lag luam tshuaj tsom mus rau kev hloov kho thiab kev hloov pauv ntawm cov tshuaj molecules, los ntawm kev qhia benzyloxycarbonyl (Cbz) tiv thaiv pab pawg lossis koom nrog cov kauj ruam tseem ceeb, txhawm rau txhim kho kev ruaj ntseg, kev ua haujlwm, thiab bioavailability ntawm cov tshuaj.

1. Amino acid thiab peptide tiv thaiv
DBAD, raws li lub hauv paus ntawm Cbz tiv thaiv pab pawg, tuaj yeem xaiv los tiv thaiv cov amino lossis carboxyl pawg ntawm cov amino acids los tiv thaiv kev mob tshwm sim thaum lub sij hawm peptide synthesis. Piv txwv li, hauv cov khoom siv -theem peptide synthesis (SPPS), Cbz tiv thaiv pab pawg tuaj yeem raug tshem tawm raws li qhov mob me me (xws li hydrogenolysis) kom tsis txhob muaj kev puas tsuaj rau lwm qhov ntawm cov saw peptide.

 

2. Synthesis ntawm cov tshuaj intermediates
DBAD tuaj yeem siv los ua ke los ua ke heterocyclic derivatives xws li indole thiab azacene, uas muaj peev xwm ua haujlwm xws li inhibiting phospholipase ntau lawm, tshuaj tua kab mob, thiab kho mob ntshav qab zib thiab atherosclerosis. Piv txwv li, los ntawm cov tshuaj tiv thaiv cycloaddition cuam tshuam nrog DBAD, heterocyclic skeletons nrog cov stereoconfigurations tshwj xeeb tuaj yeem tsim, muab cov qauv sib txawv ntawm cov neeg sib tw rau kev tshuaj xyuas tshuaj.
3. Bioactive molecule hloov kho
DBAD tuaj yeem hloov kho cov pab pawg ua haujlwm ntawm bioactive molecules (xws li nucleosides thiab qab zib) txhawm rau txhim kho lawv cov peev xwm khi nrog lub hom phiaj molecules. Piv txwv li, hauv kev txhim kho cov tshuaj tiv thaiv kab mob, DBAD kho cov tshuaj tiv thaiv glycosylation tuaj yeem ua kom zoo dua qub ntawm nucleoside analogs thiab txhim kho lawv cov haujlwm inhibitory tiv thaiv kab mob polymerases.

Cov Khoom Siv Kev Tshawb Fawb: Kev hloov pauv ntawm cov khoom siv polymer

 

Kev siv DBAD hauv cov ntaub ntawv tshawb fawb feem ntau yog tsom rau kev sib txuas thiab hloov kho cov ntaub ntawv polymer. Los ntawm kev qhia cov pab pawg azo lossis benzyloxycarbonyl pawg, cov ntaub ntawv tau txais txiaj ntsig nrog cov duab tshwj xeeb, thermal stability, thiab cov khoom siv kho tshuab.

1. Polymer catalyst
DBAD tuaj yeem siv los ua cov dawb radical pib rau cov tshuaj tiv thaiv polymerization ntawm thermoplastic hluavtaws fibers xws li polyacrylonitrile thiab polyester. Nws pawg azo decomposes nyob rau hauv cua sov los yog lub teeb tej yam kev mob los tsim dawb radicals, triggering monomer polymerization. Nyob rau tib lub sijhawm, benzyloxycarbonyl tuaj yeem tswj hwm qhov hnyav molecular faib thiab stereoregularity ntawm cov polymer.

 

2. Ua npuas ncauj polymer foaming tus neeg sawv cev
DBAD tuaj yeem siv los ua tus neeg sawv cev ua npuas dej los npaj cov- ntom ntom ua npuas ncauj polymers (xws li polyurethane thiab polystyrene). Thaum cua sov, DBAD decomposes los tsim nitrogen thiab lwm yam gases, uas nthuav cov polymer yaj los ua ib tug ntxeem tau qauv. Nyob rau tib lub sijhawm, cov khoom degradation ntawm benzyloxycarbonyl tuaj yeem txhim kho cov khoom siv dag zog thiab ua kom sov ua npuas dej.
3. Muaj nuj nqi Polymer Synthesis
Cov tshuaj tiv thaiv cycloaddition uas muaj DBAD tuaj yeem siv los tsim cov ntaub ntawv polymer nrog photoresponsiveness. Piv txwv li, los ntawm [4+2] cycloaddition cov tshuaj tiv thaiv ntawm DBAD thiab diene monomers, polymer chains uas muaj cov qauv azobenzene tuaj yeem tsim. Cov ntaub ntawv zoo li no tuaj yeem ua rau cis trans isomerization nyob rau hauv lub teeb irradiation thiab siv nyob rau hauv cov teb xws li yees duab tswj cov tshuaj tso tawm thiab cov khoom siv photochromic.

Glycochemistry: Ua kom muaj txiaj ntsig zoo ntawm Carbohydrate Derivatives

 

DBAD ua lub luag haujlwm ntawm "glycosylation reagent" hauv glycochemistry, ua tiav cov kev hloov pauv ntawm cov qauv glycation thiab kev sib txuas ntawm cov suab thaj sib txuas los ntawm cycloaddition cov tshuaj tiv thaiv nrog cov piam thaj derivatives.

1. Synthesis ntawm 2-Aminoglycosides
Lub [4+2] cycloaddition cov tshuaj tiv thaiv ntawm DBAD thiab glycerol (xws li 1,2-unsaturated qab zib) yog ib txoj kev classic rau kev sib txuas ntawm 2-aminoglycosides. Hom tshuaj tiv thaiv no muaj qhov mob me me, muaj txiaj ntsig zoo, thiab tuaj yeem qhia ntau pawg tiv thaiv (xws li benzyloxycarbonyl), muab cov ntsiab lus tseem ceeb rau kev sib txuas ntawm cov tshuaj carbohydrate.

 

2. Kev tsim kho ntawm C-glycosylated amino acids
DBAD, raws li electrophilic reagent, tuaj yeem koom nrog hauv proline catalyzed - amination cov tshuaj tiv thaiv ntawm C-glycosylaldehyde los ua ke C-glycosyl - amino acids. Cov tebchaw no muaj nuj nqis tseem ceeb hauv tag nrho cov khoom siv ntuj tsim thiab kev tsim tshuaj, xws li kev ua haujlwm zoo li cov tshuaj tua kab mob glycopeptide, uas tuaj yeem txhim kho lawv cov kab mob tua kab mob thiab kev ruaj ntseg.
3. Kev hloov kho cov suab thaj conjugates
DBAD tuaj yeem siv rau kev sib txuas ntawm cov suab thaj thiab biomolecules xws li cov proteins thiab nucleic acids, los ntawm kev tsim glycosidic lossis amide bonds los tsim cov suab thaj conjugates (xws li glycoproteins thiab nucleic acids). Hom kev hloov kho no tuaj yeem tswj hwm kev ua haujlwm lom neeg, kev ruaj ntseg, thiab cov khoom siv tshuaj biomolecules, muab cov cuab yeej tseem ceeb rau biopharmaceuticals.

Dibenzyl azodicarboxylate hmoov(DBAD) yog cov khoom siv dav siv hauv cov organic synthesis, feem ntau siv hauv photopolymerization, kev sib txuas sib txuas, thiab kev sib pauv ester. Cov txheej txheem synthesis feem ntau yog ua raws li hydrolysis ntawm azodicarbonamide (ADCA) thiab cov tshuaj tiv thaiv esterification tom qab.

Dibenzyl azodicarboxylate, tseem hu ua dibenzyl azodicarboxylate, yog daj lossis txiv kab ntxwv khoom ntawm chav tsev kub thiab siab. Azodicarboxylate dibenzyl ester belongs rau azo derivatives thiab yuav siv tau raws li cov organic synthesis tshuaj thiab tshuaj chemical condensation agents. Nws yog dav siv nyob rau hauv Mitsunobu cov tshuaj tiv thaiv thiab carboxyl functionalization cov tshuaj tiv thaiv, thiab tuaj yeem siv rau kev hloov kho thiab derivatization ntawm cov tshuaj molecules, bioactive molecules, thiab tshuaj tua kab molecules.

Daim ntawv thov hloov dua siab tshiab

Ntxiv 13.6 mmol ntawm dibenzyl azodicarboxylate rau kev daws ntawm 6.79 mmol ntawm 2-iodo-allyl cawv thiab 13.6 mmol ntawm triphenylphosphine hauv tetrahydrofuran (35 mL), do cov tshuaj tiv thaiv sib tov ntawm xoom kub rau 30 feeb, maj mam tsa cov tshuaj tiv thaiv rau 3 xuab moos. Tom qab nplawm rau 36 teev, cov tshuaj tiv thaiv sib tov yog concentrated nyob rau hauv lub tshuab nqus tsev, thiab qhov tshwm sim residue yog purified los ntawm silica gel kem chromatography (petroleum ether: ethyl acetate, 8: 1) kom tau txais cov khoom lag luam.

Dissolve chiral catalyst thiab acetaldehyde (2.0 mmol) hauv dichloromethane (0.5 mL), txias cov tshuaj tiv thaiv rau 0℃C, thiab ntxiv 0.5 mmol ntawm dibenzyl azodicarboxylate rau qhov sib tov ntawm 0℃C thaum nplawm. Tom qab paub meej tias kev noj dibenzyl azodicarboxylate los ntawm TLC qhov chaw phaj, methanol tov ntawm sodium borohydride (0.5 mmol, 20 mg) tau ntxiv rau cov tshuaj tiv thaiv thaum nplawm ntawm 0℃C. Tom qab nplawm rau 5 feeb, 1.0 mL ntawm NH4Cl aqueous tov tau ntxiv rau lub kaw lus kom tua cov tshuaj tiv thaiv. Extract cov tshuaj tiv thaiv sib tov nrog ethyl acetate (2 × 10 mL), yaug cov organic txheej nrog brine, thiab qhuav cov organic txheej nrog anhydrous MgSO4. Lim cov txheej txheem organic, ua kom pom tseeb hauv lub tshuab nqus tsev, thiab ntxuav cov khoom nyoos los ntawm silica gel kem chromatography siv ethyl acetate / n-hexane (1: 8 txog 1: 4) kom tau txais cov khoom lag luam.

Cov phom sij ntawm dibenzyl azodicarboxylate yog ib qho teeb meem nyuaj thiab muaj ntau yam teeb meem, nrog rau ntau yam xws li tib neeg kev noj qab haus huv, ib puag ncig kev nyab xeeb, thiab muaj peev xwm txaus ntshai thaum ua haujlwm. Hauv qab no yog cov ncauj lus kom ntxaws nthuav dav ntawm nws cov teeb meem:

Hauv cov ntsiab lus, qhov teeb meem ntawm dibenzyl azodicarboxylate tsis tuaj yeem tsis quav ntsej. Txhawm rau ua kom tib neeg noj qab haus huv, ib puag ncig kev nyab xeeb, thiab kev nyab xeeb thaum lub sijhawm ua haujlwm, yuav tsum tau ceev faj txog kev nyab xeeb thiab cov txheej txheem ua haujlwm.

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