Epinephrine(link:https://www.bloomtechz.com/synthetic-chemical/api-researching-only/epinephrine-powder-cas-51-43-4.html) yog ib yam tshuaj hormones thiab neurotransmitter secreted los ntawm tib neeg lub cev, tso tawm los ntawm lub qog adrenal. Nws ncaj qha ua rau adrenergic receptors, ua kom muaj zog, nrawm, thiab ntu ntu excitatory cuam tshuam, txhim kho myocardial contractility, ceev lub plawv dhia, thiab nce myocardial oxygen noj. Epinephrine muaj ntau yam kev siv tshuaj kho mob, xws li mob plawv nres, mob hawb pob bronchial, thiab kev tsis haum tshuaj. Nyob rau tib lub sijhawm, nws tseem tuaj yeem kho urticaria, cov pos hniav los ntshav, thiab qhov ntswg mucosal los ntshav. Thaum tib neeg lub cev raug rau qee yam kev xav xws li kev zoo siab, kev ntshai, thiab kev nro, adrenaline yog secreted, uas ua rau kom ua pa nrawm, muab cov pa oxygen ntau rau lub cev, ua kom cov ntshav khiav thiab lub plawv dhia, thiab nthuav cov menyuam kawm ntawv, muab lub zog tsim nyog rau kev ua si lub cev thiab ua rau tib neeg hnov mob sai dua.
Ib txoj hauv kev rau kev sib txuas adrenaline nrog ib qho enantiomer. Txoj kev no suav nrog kev siv - Halogenated acetophenone ua haujlwm raws li cov khoom pib, thiab los ntawm amination thiab txo cov tshuaj tiv thaiv, ib qho enantiomer ntawm adrenaline thaum kawg tau txais.
Kauj Ruam 1: Amination cov tshuaj tiv thaiv
Ua ntej, qhov - Halogenated acetophenones hnov mob nrog amines los ua cov sib xyaw amide sib txuas. Cov tshuaj tiv thaiv no feem ntau yog ua raws li alkaline tej yam kev mob, xws li siv sodium carbonate ua catalyst. Ib kauj ruam tseem ceeb hauv cov tshuaj tiv thaiv mechanism yog nucleophilic ntxiv, tsim ib qho imide nruab nrab.
Cov tshuaj formula: R-C6H4CH (Cl) C=O plus R'NH2 → R-C6H4CH (NHR ') C=O
Kauj Ruam 2: Txo cov tshuaj tiv thaiv
Tom ntej no, ib qho kev xaiv txo tus neeg sawv cev yog siv los txo cov amide los tsim cov amino cawv sib xyaw ua ke. Feem ntau siv cov tshuaj txo qis xws li hlau hydrides xws li lithium aluminium hydride (LiAlH4) lossis sodium hydride (NaBH4). Qhov kev txo qis no ua rau cov pab pawg carbonyl (C=O) hauv amide raug txo rau hydroxyl pawg (- OH).
Cov tshuaj formula: R-C6H4CH (NHR ') C=O plus 2 [H] → R-C6H4CH (NHR') CH2OH
Kauj Ruam 3: Tshuaj daws teeb meem
Thaum kawg, tshuaj daws teeb meem tau ua kom tau txais ib qho enantiomer ntawm adrenaline. Cov kauj ruam no feem ntau ua tiav los ntawm kev sib cais chiral, xws li siv txoj hauv kev xws li chiral kem chromatography, chiral ligand catalysts, lossis chiral derivatives. Los ntawm kev paub qhov txawv ntawm lub cev lossis cov khoom muaj zog ntawm enantiomers, sib xyaw enantiomers tuaj yeem sib cais thiab lub hom phiaj ib leeg enantiomer ntawm adrenaline tuaj yeem tau.
Cov tshuaj tiv thaiv mis (chiral sib cais): R-C6H4CH (NHR ') CH2OH → (R) - lossis (S) - adrenaline.
Cov hauv qab no yog cov ncauj lus kom ntxaws thiab muaj feem cuam tshuam cov tshuaj tiv thaiv mis rau kev npaj ib qho enantiomer ntawm adrenaline siv catechol thiab chloroacetyl chloride / chloroacetic acid ua raw cov ntaub ntawv los ntawm condensation, amination, txo, thiab tartaric acid daws cov kauj ruam:
Kauj Ruam 1: Condensation Reaction:
Ua ntej, catechins reacted nrog chloroacetyl chloride los yog chloroacetic acid los tsim chloroacetyl tiv thaiv catechol tebchaw. Cov tshuaj tiv thaiv condensation feem ntau yog ua raws li alkaline tej yam kev mob, xws li siv triethylamine (Et3N) ua ib qho catalyst.
Cov tshuaj formula: catechol plus ClCH2COCl → ClCH2C (OC6H4OH) 2
Kauj Ruam 2: Amination Reaction:
Tom ntej no, cov khoom condensation yog reacted nrog cov amine los ua tus coj amide compound. Cov tshuaj tiv thaiv amination no tuaj yeem ua tiav nyob rau hauv cov xwm txheej alkaline los txhawb cov nucleophilic ntxiv ntawm amines thiab tsim imide intermediates.
Cov tshuaj formula: ClCH2C (OC6H4OH) 2 ntxiv rau R'NH2 → ClCH2C (OC6H4OH) 2NH-R '
Kauj Ruam 3: Txo cov tshuaj tiv thaiv:
Tom qab ntawd, ib qho kev xaiv txo tus neeg sawv cev yog siv los txo cov amide los tsim cov amino cawv sib xyaw. Feem ntau siv cov tshuaj txo qis xws li hlau hydrides, xws li lithium aluminium hydride (LiAlH4) lossis sodium hydride (NaBH4). Qhov kev txo qis no ua rau cov pab pawg carbonyl (C=O) hauv amide raug txo rau hydroxyl pawg (- OH).
Cov tshuaj formula: ClCH2C (OC6H4OH) 2NH-R' ntxiv 2 [H] → ClCH2C (OC6H4OH) 2CH2NH-R'
Kauj Ruam 4: Tartaric acid sib cais:
Thaum kawg, cov racemic enantiomer tau sib cais siv tartaric acid kom tau txais ib qho enantiomer ntawm adrenaline. Tartaric acid yog ib qho chiral compound uas tuaj yeem tsim crystalline ntsev nrog racemates thiab raug cais raws li kev ua haujlwm kho qhov muag.
Cov tshuaj tiv thaiv mis (kev daws teeb meem): ClCH2C (OC6H4OH) 2CH2NH-R ' ntxiv rau C4H6O6 → (R) - lossis (S) - adrenaline ntxiv ClCH2C (OC6H4OH) 2CH2NH-R' (tartrate)
Compound a tau txais los ntawm kev siv Xinfulin hydrochloride ua raw khoom thiab tiv thaiv nrog boc pawg nyob rau hauv qhov kev txiav txim ntawm ib tug acid binding agent. Cov tshuaj b tau oxidized los ntawm 2-iodobenzoic acid thiab txo los ntawm sodium dithionite kom tau cov compound b. Cov tshuaj b yog tom qab ntawd deprotected nrog boc tiv thaiv pawg los ntawm hydrochloric acid kom tau dl adrenaline zoo li hmoov dawb. Cov kauj ruam tshwj xeeb yog raws li nram no:
Kauj Ruam 1: Npaj Cov Khoom Siv A
1. React Xinfulin hydrochloride nrog tus neeg sawv cev sib khi los ua Xinfulin khi ntsev.
2. Ntxiv BOC-OSU condensation tus neeg sawv cev (xws li N, N '- dipropylcarbodiimide) kom hnov mob nrog benzoate los tsim cov tshuaj tiv thaiv A.
Tshuaj tiv thaiv formula:
Xinfulin hydrochloride ntxiv rau acid binding tus neeg sawv cev → Xinfulin acid khi ntsev
Xinfu Linbing ntsev ntxiv rau BOC-OSU Condensing Agent → Compound A
Kauj Ruam 2: Kev Npaj Cov Khoom Siv B
1. Oxidize compound A nrog 2-iodoylbenzoic acid los tsim cov kua qaub sib xws.
2. Siv cov tshuaj txo qis xws li sodium hydrosulfite (Na2S2O4) kom txo cov kua qaub thiab tau txais cov tshuaj B.
Tshuaj tiv thaiv formula:
Compound A ntxiv rau 2-iodoylbenzoic acid → acid
Acid ntxiv rau sodium hydrosulfite → compound B
Kauj Ruam 3: Npaj DL adrenaline
1. Siv hydrochloric acid kom tshem tawm BOC tiv thaiv cov tshuaj tiv thaiv los ntawm compound B thiab rov ua kom lub ntuj hydroxyl pawg ntawm adrenaline.
2. Tom qab kev kho mob tom qab tsim nyog thiab crystallization purification, DL adrenaline zoo li hmoov dawb tau txais.
Cov tshuaj tiv thaiv kab mob (BOC tiv thaiv tshem tawm):
Cov tshuaj B ntxiv rau hydrochloric acid → DL adrenaline
(Faj seeb: Txoj kev tshwj xeeb ntawm kev tiv thaiv yuav txawv nyob ntawm qhov kev sim)