Dicyclohexylcarbodiimide hmoov(DCC), CAS 538-75-0, yog tus neeg saib xyuas kev sib txuas ua haujlwm. Nws yog ib qho dawb, tsw ntxhiab siv lead ua los yog me ntsis daj pob tshab kua nrog lub melting point tsawg. Nws yog soluble hauv dichloromethane, tetrahydrofuran, acetonitrile, thiab dimethylformamide, tab sis insoluble hauv dej. Cov tshuaj formula yog C13H22N2, thiab cov cn=c=nc ib feem ntawm lub molecule tsis yog ib tug qauv, tab sis ib tug orthogonal kev npaj, zoo ib yam li propylene diene. Nws yog ib qho kev siv lub cev qhuav dej hauv esterification, amidation thiab lwm yam kev cuam tshuam, thiab tseem tuaj yeem siv rau kev sib txuas ntawm anhydrides, aldehydes, ketones thiab isocyanates. DCC yog ib qho ntawm cov nquag siv activators, uas tuaj yeem txhawb kev sib xyaw ua ke ntawm cov amino acids thiab ua kom muaj txiaj ntsig zoo peptide chains. Hauv Fmoc solid-phase synthesis, DCC activates carboxyl pawg thiab txhawb kev tsim ntawm amide bonds ntawm carboxyl pawg ntawm cov amino acid thiab cov amino pawg ntawm lwm cov amino acid. DCC pab tsim activated esters nyob rau hauv ester synthesis, txhim kho cov tshuaj tiv thaiv efficiency thiab tawm los. Steglich esterification cov tshuaj tiv thaiv yog ib txoj hauv kev siv ntau tshaj plaws hauv DCC esterification cov tshuaj tiv thaiv, feem ntau nqa tawm ntawm chav tsev kub, haum rau cov substrates nrog siab steric hindrance los yog acid rhiab heev.
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Tshuaj Formula |
C13H22N2 |
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Exact Mass |
206 |
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Molecular Luj |
206 |
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m/z |
206 (100.0%), 207 (14.1%) |
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Elemental Analysis |
C, 75.68; H, 10.75; N, 13.58 |
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Cyclohexylamine thiab cyclohexyl isonitrile yog ua ke los tsim DCC raws li kev txiav txim ntawm palladium acetate, iodine thiab oxygen, thiab cov txiaj ntsig tuaj yeem ncav cuag 67%.
Ob lub molecules ntawm cyclohexyl isocyanate tau condensed los ua DCC nyob rau hauv lub catalysis ntawm op (mench2ch2) 3N, nrog ib tug yield ntawm 92%
Dicyclohexylurea reacts nrog arylsulfonyl chloride, potassium carbonate thiab benzyltrimethylammonium chloride (theem hloov catalyst) los tsim DCC.
Dicyclohexyl thiourea txoj kev yog tsim los ntawm cov tshuaj tiv thaiv ntawm cyclohexylamine thiab carbon disulfide los tsim n, n'- dicyclohexyl thiourea, uas yog tau los ntawm dehydrogenation.
Dicyclohexylamine urea txoj kev kuj tuaj yeem tau txais los ntawm kev ua haujlwm n, n'- dicyclohexylurea nrog phosphorus pentoxide hauv pyridine.
Ua n, n 'ib ob lub nplhaib puag mem tes
240 g (2.42 mol) ntawm cyclohexylamine tau refluxed nrog 60 g (1.00 mol) ntawm urea hauv 480 ml ntawm isoamyl cawv rau 20 teev. Tom qab txias, lim tawm cov siv lead ua, ntxuav nws nrog ether, thiab qhuav kom tau 200 grams ntawm N, n 'dicyclohexyl dolphin, nrog rau 89%.
Kev npaj ntawm dicyclohexyl carbodiimide
200 g (0.891 mol) ntawm dicyclohexyl chloride thiab 300 g (1.574 mol) ntawm toluene sulfonyl chloride tau nplawm hauv 600 ml ntawm anhydrous pyridine ntawm 70℃rau 1 teev. Ncuav lub reactant rau hauv 1.5 kg crushed ice thiab extract nrog ether. Ntxuav thiab qhuav cov tshuaj ether nrog dej. Evaporate cov ether, thiab evaporate cov residue nyob rau hauv lub siab txo . 152 grams (82%) ntawm dicyclohexyl carbodiimide tau txais
Dicyclohexylcarbodiimide hmoov(DCC) yog ib qho tseem ceeb organic compound nrog ntau yam kev siv.
Organic synthesis
DCC feem ntau yog siv los ua lub cev qhuav dej hauv cov organic synthesis, tshwj xeeb tshaj yog nyob rau hauv esterification thiab amidation tshua.
Esterification thiab amidation cov tshuaj tiv thaiv:
DCC tuaj yeem txhawb nqa lub cev qhuav dej ntawm cov carboxylic acids thiab cawv lossis amines, tsim cov ester lossis amide bonds. Cov tshuaj tiv thaiv mob yog me me, thiab cov synthesis tawm los feem ntau yog siab.
Hauv peptide synthesis, DCC feem ntau siv rau hauv cov tshuaj tiv thaiv condensation ntawm cov amino acids los pab tsim peptide bonds.
Lwm cov tshuaj tiv thaiv:
DCC tuaj yeem siv rau kev sib txuas ntawm anhydrides, aldehydes, ketones, thiab isocyanates. DCC yog qhov yooj yim tshaj plaws, cov tshuaj tiv thaiv zoo tshaj plaws, thiab cov txiaj ntsig siab tshaj plaws coupling reagent nyob rau hauv cov synthesis ntawm acid anhydrides.
DCC tuaj yeem ua rau muaj kev cuam tshuam xws li kev hloov pauv ntawm thiourea rau cyanoguanidine, ua kom pom tias nws muaj ntau yam hauv cov organic synthesis.
Kev kho mob teb
DCC muaj ntau yam kev siv hauv kev lag luam tshuaj thiab yog ib feem tseem ceeb ntawm ntau cov txheej txheem tshuaj synthesis.
Tshuaj synthesis:
DCC yog qhov zoo qis -kub biochemical dehydrating tus neeg sawv cev siv rau kev sib txuas thiab lub cev qhuav dej ntawm amikacin thiab amino acids.
Nws kuj tseem siv rau kev sib txuas ntawm peptides thiab nucleic acids, nrog rau kev tsim cov tshuaj xws li vasopressin thiab cyclic adenosine monophosphate. Hauv cov kev cuam tshuam no, DCC tuaj yeem txhawb nqa qhov sib xyaw ua ke ntawm carboxylic acids thiab amines, tsim kev ruaj khov amide bonds.
Drug carrier:
DCC tuaj yeem siv los ua ob peb cov tshuaj molecules nrog cov cab cov proteins, txhim kho cov hom phiaj tshuaj thiab kev ruaj ntseg. Cov tshuaj tiv thaiv kev sib txuas no pab ua kom tiav cov tshuaj tso tawm hauv lub cev thiab txhim kho kev ua haujlwm zoo.
Tshuaj tua kab
DCC kuj muaj qee yam kev siv tshuaj tua kab, feem ntau yog siv los ua cov tshuaj tua kab nruab nrab.
Cov intermediates no tuaj yeem ua rau muaj kev cuam tshuam ntxiv los npaj cov khoom siv tshuaj tua kab xws li tshuaj tua kab thiab tshuaj tua kab. Kev ua kom lub cev qhuav dej zoo ntawm DCC ua rau nws ua lub luag haujlwm tseem ceeb hauv cov tshuaj hluavtaws no.
Dye field
DCC tuaj yeem siv rau kev sib txuas ntawm dyes, pab txhim kho lawv cov xim thiab ceev ceev.
Los ntawm lub cev qhuav dej ntawm DCC, dyes molecules nrog cov qauv tshwj xeeb thiab cov khoom muaj peev xwm tuaj yeem ua ke kom tau raws li qhov kev thov rau siab - cov xim zoo nkauj hauv kev lag luam dye.
Lwm yam teb
Ntxiv nrog rau cov lus hais saum toj no, DCC muaj ntau yam kev siv hauv cov khoom siv kho mob, tshuaj pleev ib ce, luam ntawv thiab dyeing, biologics, thiab lwm yam.
Khoom noj khoom haus thiab tshuaj pleev ib ce:
DCC tuaj yeem siv los ua ke qee qhov sib txuas nrog cov txiaj ntsig kev noj qab haus huv, nrog rau cov khoom xyaw nquag hauv cov tshuaj pleev ib ce.
Printing thiab dyeing, biological agents:
Hauv kev lag luam luam ntawv thiab dyeing, DCC tuaj yeem siv rau kev kho dye fixation los txhim kho kev ntxuav thiab lub teeb tsis kam ntawm dyes.
Hauv kev lag luam biologics, DCC tuaj yeem siv los ua ke qee yam biomolecules, xws li cov proteins, nucleic acids, thiab lwm yam.
Tsis tas li ntawd, nws tsim nyog hais tias DCC tseem muaj peev xwm thov kev cia siab rau hauv lithium roj teeb electrolyte additives. Txawm hais tias daim ntawv thov hauv daim teb no tseem tsis tau muaj kev lag luam, ib zaug ua tiav, nws yuav nthuav dav ntau qhov chaw lag luam ntawm DCC.
Dicyclohexylcarbodiimide hmoov(DCC), uas yog ib qho tseem ceeb ntawm cov organic compound, muaj ntau yam kev siv hauv cov organic synthesis, tshuaj, tshuaj tua kab, dyes, thiab lwm yam. Muaj ob txoj hauv kev tseem ceeb rau nws txoj kev npaj: cov tshuaj tiv thaiv ntawm cyclohexylamine nrog carbon disulfide thiab cov tshuaj tiv thaiv ntawm dicyclohexylurea nrog trichloromethyl carbonate. Hauv qab no yog cov lus piav qhia ntxaws ntawm ob txoj kev npaj no:
Cov tshuaj tiv thaiv cyclohexylamine nrog carbon disulfide
1. Cov kev mob tshwm sim
Nyob rau hauv tej yam kev mob, cyclohexylamine reacts nrog carbon disulfide los tsim dicyclohexylthioperoxide, uas yog dehydrogenated kom tau DCC. Thaum lub sij hawm tus txheej txheem no, catalysts xws li triethylbenzyl ammonium chloride (TEBA) los yog polyethylene glycol ua lub luag haujlwm tseem ceeb.
2. Cov tshuaj tiv thaiv mechanism
Kauj Ruam 1: Cyclohexylamine reacts nrog carbon disulfide los tsim cyclohexyl thiourea thiab sodium sulfide.
Kauj Ruam 2: Nyob rau hauv oxidation ntawm sodium hypochlorite, cyclohexyl thiourea raug oxidation theem nrab kom tshem tawm hydrogen sulfide thiab tsim DCC.
Kauj Ruam 3: Ntxiv sodium sulfide rau cov txheej txheem organic sib cais thiab hnov mob nrog sulfur kom tshem tawm cov sulfur.
3. Qhov zoo thiab qhov tsis zoo
qhov zoo:
Cov khoom muaj siab purity thiab tawm los.
Tsawg dua los ntawm - cov khoom lag luam thiab kev ntseeg siab ua haujlwm tau zoo.
Sulfur yuav tsis nyob hauv cov khoom thiab tsis tas yuav raug tshem tawm los ntawm sodium sulfide.
Cov kuab tshuaj rov siv dua thiab rov siv dua muaj cov khoom siv rov ua dua tshiab thiab cov txiaj ntsig zoo nyiaj txiag.
Qhov tsis zoo:
Cov dej khib nyiab tuaj yeem raug tsim tawm thaum lub sijhawm tsim khoom, ua rau muaj kev ntxhov siab rau ib puag ncig. Txawm li cas los xij, los ntawm kev ua kom zoo dua cov txheej txheem, xws li siv cov desulfurizers, tiam ntawm cov dej khib nyiab tuaj yeem txo tau zoo.
Cov tshuaj tiv thaiv ntawm Dicyclohexylurea nrog Trichloromethyl Carbonate
1. Cov kev mob tshwm sim
Dicyclohexylurea reacts nrog trichloromethyl carbonate nyob rau hauv qhov kev txiav txim ntawm lub catalyst los tsim DCC. Catalysts feem ntau yog anhydrous ferric chloride, zinc chloride, thiab lwm yam. loaded ntawm molecular sieves.
2. Cov tshuaj tiv thaiv mechanism
Dicyclohexylurea reacts nrog trichloromethyl carbonate nyob rau hauv qhov kev txiav txim ntawm lub catalyst los tsim DCC.
Cov tshuaj tiv thaiv no ua tiav cov txheej txheem lub cev qhuav dej los ntawm carbonyl alcoholization.
3. Qhov zoo thiab qhov tsis zoo
qhov zoo:
High kev nyab xeeb yam thiab siab catalytic efficiency.
Tsawg pov tseg, siab purity thiab tawm los, haum rau kev lag luam ntau lawm.
Qhov tsis zoo:
Lub byproduct ntawm DCC cov tshuaj tiv thaiv, dicyclohexylurea, muaj tsawg solubility nyob rau hauv cov organic solvents, uas ua rau tej yam nyuaj rau cov txheej txheem purification. Feem ntau, tom qab distilling tawm cov tshuaj hnyav, cov kuab tshuaj xws li ether raug ntxiv los pab lim tawm los ntawm - khoom.
Ob txoj kev npaj no txhua tus muaj lawv tus kheej qhov zoo thiab qhov tsis zoo, thiab kev xaiv ntawm txoj kev yog nyob ntawm cov kev xav tau tshwj xeeb, cov khoom siv, thiab cov kev cai ib puag ncig. Cov tshuaj tiv thaiv ntawm cyclohexylamine thiab carbon disulfide yog tsim rau cov xwm txheej uas yuav tsum tau siab purity thiab tawm los, thaum cov tshuaj tiv thaiv ntawm dicyclohexylurea thiab trichloromethyl carbonate yog tsim nyog rau cov xwm txheej uas yuav tsum tau loj -scale industrial ntau lawm thiab tsom rau kev nyab xeeb thiab kev tiv thaiv ib puag ncig.
DCC hais txog N, N '- dicyclohexylcarbodiimide, feem ntau siv lub cev qhuav dej, dav siv hauv cov organic synthesis, tshwj xeeb tshaj yog nyob rau hauv esterification lossis amidation cov tshuaj tiv thaiv nrog cov mob me thiab feem ntau cov synthesis siab yields. Nws lub luag haujlwm tseem ceeb yog hloov cov pawg hydroxyl hauv carboxylic acids rau hauv cov acyl intermediates, yog li txhawb kev tsim ntawm amides lossis esters.
Cov piv txwv tshwj xeeb cov tshuaj tiv thaiv:
DCC feem ntau yog siv rau hauv peptide synthesis thiab hauv cov tebchaw uas amines hnov mob nrog carboxylic acids los ua amide bonds, nrog cov tshuaj tiv thaiv siab thiab cov tshuaj tiv thaiv sai. Tsis tas li ntawd, DCC yog qhov yooj yim tshaj plaws, cov tshuaj tiv thaiv zoo tshaj plaws, thiab cov txiaj ntsig siab tshaj plaws sib txuas reagent rau kev sib txuas ntawm cov kua qaub anhydrides.
Thaum nws los txog rau cov tshuaj tiv thaiv esterification, Steglich esterification cov tshuaj tiv thaiv yog ib txoj hauv kev siv ntau tshaj plaws. Cov tshuaj tiv thaiv no tau tshaj tawm thawj zaug los ntawm Wolfgang Steglich hauv xyoo 1978, siv DCC ua tus neeg sawv cev thiab lub cev qhuav dej, DMAP ua cov khoom siv, los txhawb cov tshuaj tiv thaiv esterification hauv cov mob me. Cov tshuaj tiv thaiv feem ntau yog nqa tawm ntawm chav tsev kub, thiab dichloromethane feem ntau yog siv los ua cov kuab tshuaj, uas yog tsim rau cov substrates nrog siab steric hindrance los yog acid rhiab heev, tshwj xeeb tshaj yog rau kev npaj ntawm tert butyl ester. Txawm li cas los xij, txoj kev Fischer esterification ib txwm muaj (acid catalyzed esterification) tuaj yeem ua rau tshem tawm cov tshuaj tiv thaiv thaum kho tert butanol. Tsis tas li ntawd, cov tshuaj tiv thaiv no kuj tuaj yeem siv rau kev sib txuas ntawm thioesters. Lub cev qhuav dej byproduct DCC hauv cov tshuaj tiv thaiv yog hloov mus rau hauv dicyclohexylurea (DCU), uas feem ntau ua rau muaj teeb meem hauv kev tshem tawm cov khoom lag luam. Rau cov khoom uas tsis tshua muaj polarity, DCU tuaj yeem raug tshem tawm zoo los ntawm kev ua kom zoo thiab lim nrog ether, methyl tertiary ether, lossis cov kuab tshuaj sib xyaw.
Cov tshuaj tiv thaiv ntawm cawv oxidation rau aldehydes thiab ketones los ntawm DCC thiab DMSO kuj hu ua Pfitzner Moffatt oxidation. Bronsted acid feem ntau ntxiv rau catalyze cov tshuaj tiv thaiv. Nws muaj qhov zoo ntawm cov tshuaj tiv thaiv me me, tab sis nws tsim los ntawm - cov khoom xws li urea uas nyuaj rau tshem tawm, thiab nws muaj feem cuam tshuam rau kev cuam tshuam xws li sulfur etherification, uas kuj yog qhov tsis zoo ntawm cov tshuaj tiv thaiv no.
Raws li kev txiav txim ntawm DCC, thiourea tuaj yeem hloov mus rau cyanoguanidine raws li qhov tsim nyog cov tshuaj tiv thaiv.
Ntxiv rau,Dicyclohexylcarbodiimide hmoovfeem ntau yog siv los ua kom lub cev qhuav dej rau kev sib txuas nrog qee yam tshwj xeeb ua haujlwm. Nyob rau hauv lub xub ntiag ntawm catalytic CuCl, DCC tuaj yeem ua tus neeg saib xyuas lub cev kom zoo rau cov cawv, esters, enamines, thiab nitro compounds.
Cov lus nug nquag
DCC ua dab tsi hauv cov tshuaj tiv thaiv?
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DCC yog lub cev qhuav dej rau kev npaj ntawm amides, ketones, thiab nitriles. Hauv cov tshuaj tiv thaiv no, DCChydrates los tsim dicyclohexylurea (DCU), ib tug compound uas yuav luag insoluble nyob rau hauv feem ntau cov organic solvents thiab insoluble nyob rau hauv dej.
Kev siv DCC reagent yog dab tsi?
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N,N'-dicyclohexylmethanediimine, feem ntau hu ua DCC, yog ib qho kev lees paub dav dav siv dav siv rauprotein coupling thiab ntau yam amide daim ntawv cog lus - tsim cov tshuaj tiv thaiv uas muaj cov thawj thiab theem nrab amines nrog carboxylic acids.
Dab tsi yog cov txiaj ntsig ntawm DCC?
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Qee qhov kev tshawb fawb tshiab tau pom tias DCC tuaj yeem muaj txiaj ntsig zoo rau ob qho tib si preterm thiab puv - cov me nyuam mos. Cov txiaj ntsig no suav nrogKev nce ntshav hauv placental, nce 60% ntawm RBCs thiab 30% nce hauv cov ntshav me nyuam mos.. Lwm qhov zoo ntawm DCC yog qhov txo qis ntawm cov hlau deficiency anemia.
DCC txhais li cas kev kho mob?
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Kev puas tsuaj ntawm corpus callosum(DCC) yog qhov sib txawv ntawm kev loj hlob ntawm lub hlwb. Lawv tshwm sim thaum lub corpus callosum, ib feem ntawm lub hlwb uas txuas ob lub hemispheres, tsis tsim tag nrho (ageenesis) los yog tsim txawv (dysgenesis).
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