1,1'-Carbonyldiimidazole CAS 530-62-1

1,1'-Carbonyldiimidazole, alias N.N'- carbonyl diimidazole, 1,1'- carbonyl diimidazole thiab carbonyl diimidazole, molecular mis C7H6N4O, CAS 530-62-1, molecular yuag 162.15, dawb crystalline hmoov, insoluble nyob rau hauv dej, soluble nyob rau hauv cawv thiab e. Carbonyl diimidazole yog ib hom tshuaj uas muaj zog reactivity. Nws tuaj yeem cuam tshuam nrog^-COOJ,^-NH2,^-OH thiab lwm pab pawg ua haujlwm los ua ke ntau ketones, esters, ureas thiab lwm cov tebchaw uas nyuaj kom tau txais los ntawm ntau txoj hauv kev. Piv txwv li, cov tshuaj tiv thaiv nrog amine tuaj yeem tsim cov tshuaj tua kab imidazole, thaum tsis txhob siv cov tshuaj phosgene uas tsis yooj yim rau khaws thiab thauj. Feem ntau yog siv rau cov organic synthesis, tshuaj tua kab thiab tshuaj intermediates.

Raws li kev ua haujlwm siab carbonylation reagent,1,1'-Carbonyldiimidazole(CDI) tau qhia dav daim ntawv thov tus nqi hauv cov organic synthesis, biochemistry, cov ntaub ntawv tshawb fawb thiab tshuaj vim nws cov qauv tshuaj tshwj xeeb thiab cov yam ntxwv ntawm cov tshuaj tiv thaiv.

1. Core cov tshuaj tiv thaiv mechanism thiab tshuaj muaj zog

 

CDI molecule muaj ob lub nplhaib imidazole txuas los ntawm pawg carbonyl. Nws pab pawg carbonyl yog qhib los ntawm cov hluav taws xob muaj zog - rho tawm ntawm lub nplhaib imidazole los ua ib qho chaw zoo heev reactive carbon zoo. Cov qauv no ua rau nws muaj kev cuam tshuam nrog cov pab pawg ua haujlwm uas muaj cov nquag hydrogen (xws li -COOH, -NH₂, -OH) los tsim cov intermediates xws li acyl imidazole, carbamoyl imidazole lossis ester imidazole. Cov intermediates no tuaj yeem cuam tshuam nrog nucleophiles (xws li amines, cawv, thiols) los tsim cov khoom lag luam xws li amides, esters, ureas, thiab carbamates. Nws cov yam ntxwv tshuaj tiv thaiv muaj xws li:

 

 

Kev xaiv siab: Hauv thawj amine / theem nrab amine coexistence system, thawj amines yog qhov nyiam ua haujlwm ntawm chav tsev kub, thiab kev ua haujlwm ntawm ob pawg ua haujlwm tuaj yeem ua tiav los ntawm kev tswj xyuas kev mob.

Cov tshuaj tiv thaiv me me: tsis muaj cov kua qaub muaj zog, lub hauv paus muaj zog lossis kub siab, thiab cov tshuaj tiv thaiv tuaj yeem ua tiav ntawm chav tsev kub txog 60 degree.
Intermediate stability: lub generated acyl imidazole intermediate tuaj yeem nyob ruaj khov hauv cov kuab tshuaj organic rau ob peb teev, uas yooj yim rau kauj ruam -los ntawm - kauj ruam ua haujlwm.
Tsis yog - lwm yam tshuaj lom: nws tuaj yeem hloov cov tshuaj lom phosgene (COCl₂) rau kev sib txuas ntawm isocyanates thiab urea compounds.

2. Lub luag haujlwm tseem ceeb hauv peptide thiab protein synthesis

 

1. High -kev ua tau zoo coupling tus neeg sawv cev rau peptide daim ntawv cog lus tsim
CDI yog ib qho tseem ceeb reagent nyob rau hauv cov khoom theem peptide synthesis (SPPS) thiab kua theem peptide synthesis, thiab nws cov txheej txheem ntawm kev txiav txim muaj xws li:
Kev ua kom ncaj qha ntawm carboxylic acid: reacts nrog pawg carboxyl ntawm cov amino acids los tsim acyl imidazole, uas tom qab ntawd condenses nrog cov amino pawg ntawm lwm cov amino acid los tsim ib daim ntawv cog lus peptide. Piv txwv li, nyob rau hauv cov synthesis ntawm antimicrobial peptide LL-37, CDI coupling txoj kev yuav ua rau kom cov yield los ntawm 15% -20% piv nrog cov tsoos DCC / HOBt txoj kev, thaum txo cov racemization sab cov tshuaj tiv thaiv.
Kev tiv thaiv hauv cheeb tsam: los ntawm kev kho cov tshuaj tiv thaiv, xaiv kev tiv thaiv ntawm N-terminus lossis C-terminus tuaj yeem ua tiav. Piv txwv li, thaum synthesizing cyclic peptides, CDI muaj peev xwm nyiam ua kom lub sab saw carboxyl pawg kom tsis txhob tsim ntxov ntxov ntawm cov saw tseem ceeb peptide bonds.

 

Peptide kev hloov kho thiab kev faib tawm: Siv cov pab pawg carboxyl qhib los ntawm CDI, cov ntawv fluorescent, polyethylene glycol (PEG) lossis kev hloov kho dendrimer tuaj yeem qhia tau. Piv txwv li, fluorescein isothiocyanate (FITC) yog ua ke rau lysine sab saw ntawm insulin los ntawm CDI kom ua tiav cov tshuaj nrhiav pom.

2. Protein cross-txuas thiab immobilization
CDI-kev sib haum xeeb hla- kev sib txuas cov kev sib txuas tuaj yeem tsim xoom-ntev amide bonds lossis ib zaug -carbon spaced carbamate bonds ntawm cov protein molecules:
Enzyme immobilization: Glucose oxidase (GOx) yog immobilized nyob rau saum npoo ntawm cov amino- hloov magnetic nanoparticles los ntawm activating carboxyl pawg los ntawm CDI. Kev ua haujlwm rov qab ntawm cov enzyme immobilized nce mus txog 92%, thiab nws tuaj yeem rov qab siv ntau dua 10 zaug.
Kev npaj cov tshuaj tiv thaiv kab mob-antigen complexes: Hauv kev sib xyaw ntawm cov khoom siv tshuaj tiv thaiv kab mob, CDI tuaj yeem ua ob peb cov protein A rau hydroxylated carriers (xws li agarose gel) los ua ib txheej siab -affinity adsorption txheej rau kev ua kom huv ntawm IgG hauv ntshav.

3. Multifunctional Applications hauv Organic Synthesis

 

1. Synthesis ntawm Ketones, Ester thiab Urea Compounds
Synthesis of Ketones: CDI reacts nrog organometallic reagents (xws li Grignard reagents) kom zoo tsim ketone pob txha. Piv txwv li, nyob rau hauv cov synthesis ntawm acetophenone, CDI txoj kev tsub kom lub yield los ntawm 12% piv nrog cov tsoos acyl chloride txoj kev thiab zam lub tiam ntawm hydrogen chloride.
Synthesis ntawm Ester: CDI activates carboxylic acids thiab condenses lawv nrog cawv los ua esters. Txoj kev no muaj qhov zoo tseem ceeb hauv kev sib txuas ntawm chiral esters. Piv txwv li, nyob rau hauv kev npaj ntawm cov intermediates tseem ceeb ntawm cov tshuaj tiv thaiv kab mob oseltamivir, CDI txoj kev tuaj yeem tswj cov enantiomeric tshaj (ee) mus rau ntau dua 99%.
Urea Compounds: CDI reacts nrog amines los tsim carbamoyl imidazole intermediates, uas ntxiv condensed nrog lwm amine los tsim urea. Txoj kev no ua rau luv luv cov kauj ruam los ntawm 2 cov kauj ruam piv nrog cov txheej txheem phosgene thaum sib txuas cov tshuaj tua kab mob fluroxypyr, thiab nce kev siv atomic los ntawm 30%.

 

2. Tsis yog -phosgene Synthesis ntawm Isocyanates
CDI reacts nrog amines los tsim isocyanates, tsis txhob siv cov tshuaj lom phosgene. Piv txwv li, thaum synthesizing polyurethane raw khoom toluene diisocyanate (TDI), CDI txoj kev tuaj yeem txo lub sij hawm cov tshuaj tiv thaiv los ntawm 8 teev mus rau 2 teev, thiab cov khoom purity ncav cuag 99.5%.

3. Kev tsim kho ntawm heterocyclic compounds
CDI tuaj yeem siv los ua tus neeg pub nyiaj carbonyl los koom rau hauv heterocyclic synthesis:

Imidazolopyridines: Los ntawm cov tshuaj tiv thaiv cyclization ntawm CDI thiab 2-aminopyridine, imidazo [1,2-a] pyridine skeleton nrog antitumor kev ua haujlwm tuaj yeem tsim tau zoo.
-lactam tshuaj tua kab mob intermediates: CDI reacts nrog penicillin V poov tshuaj ntsev rau synthesize 7-aminocephalosporanic acid (7-ACA), ib tug tseem ceeb intermediate ntawm cephalosporin tshuaj tua kab mob, nrog ib tug yield nce los ntawm 18% piv nrog ib txwm tshuaj txoj kev.

4. Nto hloov tshuab hauv cov ntaub ntawv tshawb fawb

 

1. Polymer functionalization
1,1'-Carbonyldiimidazoletuaj yeem ua kom paub cov molecules ua haujlwm rau hauv cov chaw polymer los ntawm covalent bonds:

Kev hloov pauv biocompatibility: Nyob rau saum npoo ntawm polylactic acid-co-glycolic acid (PLGA), CDI tuaj yeem ua ob peb polyethylene glycol (PEG) lossis RGD peptide, txo cov immunogenicity ntawm cov khoom thiab txhawb nqa cell adhesion.

Kev hloov pauv ntawm cov khoom siv hluav taws xob: Ntawm qhov chaw ntawm polypyrrole (PPy), CDI tuaj yeem immobilize qabzib oxidase los tsim kom muaj cov piam thaj rhiab heev nrog kev kuaj pom tsawg li 0.1μM.

 

2. Nanomaterial nto engineering
CDI tuaj yeem ua tiav qhov kev ua haujlwm ntawm nanoparticles:

Kev hloov kho Quantum dot: CDI yog siv rau ob peb carboxylated CdSe quantum dots nrog amino antibodies los tsim fluorescent immunoprobes rau kev kuaj pom cov qog marker CA125 nrog rhiab heev ntawm 0.1ng / mL.

Kev ua haujlwm ntawm cov hlau nplaum nanoparticles: Nyob rau saum npoo ntawm Fe₃O₄, CDI tuaj yeem ua ob peb folic acid molecules kom ua tiav cov kev paub tshwj xeeb ntawm cov qog hlwb los ntawm cov phiaj xwm xa tshuaj.

5. Pharmaceutical intermediates thiab tshuaj synthesis

 

1. Synthesis ntawm tshuaj tua kab mob intermediates
CDI yog irreplaceable nyob rau hauv lub synthesis ntawm -lactam tshuaj tua kab mob:

Cephalosporin C sab saw hloov: CDI ua kom cov carboxyl pawg ntawm cephalosporin C, thiab tuaj yeem qhia cov aminothiazole sab chains los tsim cov qauv tseem ceeb ntawm peb - tiam cephalosporin.
Penicillin V potassium ntsev hloov pauv: CDI tuaj yeem hloov penicillin V potassium ntsev rau hauv 6-aminopenicillanic acid (6-APA) nrog cov txiaj ntsig ntawm 95%, thiab zam kev siv cov tshuaj chloroformate heev.

 

2. Cov nruab nrab tseem ceeb ntawm cov tshuaj tiv thaiv kab mob
Thaum synthesizing cov tshuaj tiv thaiv kab mob HIV efavirenz, CDI tuaj yeem txhim kho cov urea pawg hauv nws cov qauv tseem ceeb, ua kom luv cov kauj ruam los ntawm 3 cov kauj ruam piv nrog cov kab ke ib txwm muaj, thiab tag nrho cov txiaj ntsig tau nce los ntawm 45% mus rau 68%.

3. Anti- kho mob qog noj ntshav
CDI tuaj yeem siv rau kev hloov kho PEGylation ntawm cov tshuaj paclitaxel, xws li kev sib txuas mPEG-2000 mus rau 2'-hydroxyl pawg paclitaxel los ntawm CDI, txuas ntxiv ib nrab-lub neej ntawm cov tshuaj (los ntawm 2.8 teev mus rau 24 teev) thiab txo cov immunogenicity.

Synthesis ntawm1,1'-Carbonyldiimidazole:

Lub imidazole yog reacted nrog phosgene yaj nyob rau hauv benzene, lub imidazole hydrochloride nyob rau hauv lub reactant yog lim, thiab cov filtrate yog concentrated kom tau 1,1'- carbonyldiimidazole nrog ib tug yield ntawm 91%.

Ncuav 200 ml ntawm anhydrous benzene rau hauv 500 ml conical funnel thiab hnyav nws nrog ib tug stopper. Tshem lub iav ntsaws thiab nruab ib lub raj xa hluav taws xob nrog cov xuab zeb lim ntawm lub funnel. Nyob rau hauv kev tiv thaiv ntawm chav tsev kub thiab ziab tube, txog 20g phosgene yog qhia nyob rau hauv txog 1h (lub ntim ntawm benzene tov nce li ntawm 12-16ml). Txuas lub funnel thiab ntsuas nws tam sim ntawd. Qhov hnyav ntawm phosgene yog 16.55 g (0.167 mole). Yog li, qhov xav tau ntawm imidazole yog xam raws li molar piv ntawm phosgene rau imidazole ntawm 1: 4. Tom qab ntawd, nruab lub funnel rau ntawm peb lub caj dab lub raj mis uas muaj 45.60g (0.669mol) imidazole thiab 500ml anhydrous tetrahydrofuran. Nyob rau hauv txias thiab electromagnetic stirring, tso cov tshuaj benzene ntawm phosgene hauv 15-30 feeb. Txuas ntxiv sib tov rau 15 feeb, thiab cia sawv ntsug ntawm chav sov li 1 teev. Hauv qhov chaw qhuav, tshem tawm imidazole hydrochloride nrog xuab zeb core funnel. Cov filtrate yog concentrated rau dryness nyob rau hauv 40 ~ 50℃thiab txo siab kom tau 24.5g (91%) ntawm cov xim tsis muaj kob.

Ceev faj! Phosgene yog tshuaj lom, thiab qhov no yuav tsum tau ua nyob rau hauv lub fume hood.

1. Lo lus nug: Raws li kev sib txuas reagent, qhov zoo ntawm CDI piv nrog cov tsoos DCC lossis EDC yog dab tsi?
Qhov zoo tshaj plaws ntawm CDI yog nyob rau hauv qhov tseeb tias nws cov tshuaj tiv thaiv los ntawm - cov khoom tsuas yog imidazole thiab carbon dioxide, ob qho tib si yog volatile los yog yooj yim tshem tawm tsawg- tshuaj toxicity, yog li zam qhov teeb meem uas reagents zoo li DCC yuav ua rau nyuaj-rau- tshem tawm los ntawm - khoom ( as DCU). Qhov no ua rau tom qab purification yooj yim dua thiab cov khoom purity siab dua, tshwj xeeb tshaj yog haum rau cov synthesis ntawm peptides los yog tshuaj uas rhiab heev rau impurities.

2. Q: Dhau li ntawm kev siv cov synthesis ntawm amides, CDI muaj lwm yam kev siv tshwj xeeb?
Teb: Ib daim ntawv thov tseem ceeb yog qhov kev npaj ua tau zoo thiab maj mam ntawm cov esters nquag. CDI thawj zaug reacts nrog carboxylic acids los tsim cov active acylimidazole intermediates, uas tuaj yeem hnov ​​​​mob nrog N-hydroxysuccinimide (NHS) thiab lwm tus los tsim NHS active esters ruaj khov. Cov esters nquag no tau siv dav hauv kev sib xyaw ua ke lom neeg thiab hloov pauv cov protein vim tias lawv qhov kev ruaj ntseg zoo nyob rau theem aqueous.

3. Q: Dab tsi yuav tsum tau ceev faj txog kev nyab xeeb thaum siv thiab khaws cia CDI?
Teb: CDI yog qhov rhiab heev rau cov dej noo. Thaum nws los rau hauv kev sib cuag nrog dej, nws yuav sai sai hydrolyze thiab tso carbon dioxide, uas yuav ua rau kom nce siab nyob rau hauv lub ntim ntim. Yog li, nws yuav tsum tau ua haujlwm thiab khaws cia rau hauv qhov chaw tsis muaj dej tsis zoo xws li nitrogen lossis argon. Lub caij no, CDI nws tus kheej yog khaus heev thiab tuaj yeem ua rau lub qhov muag, tawv nqaij thiab ua pa. Cov cuab yeej tiv thaiv tsim nyog (hnab looj tes, hnab looj tes, fume hoods) yuav tsum hnav thaum ua haujlwm.

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