5-IODOINDOLEyog ib qho organic compound, uas yog ib qho isomer uas muaj iodine atom ntawm cov tub ntxhais Indian, thiab muaj ntau yam kev siv, xws li kev lag luam tshuaj, kev tshawb fawb biochemical thiab lwm yam kev lag luam. Cov hauv qab no yog qee qhov kev sib xyaw ua ke ntawm 5-IODOINDOLE:
1. Cov tshuaj tiv thaiv Sandmeyer:
Cov tshuaj tiv thaiv Sandmeyer yog ib qho ntawm ntau tshaj 5-iodoindole synthesis txoj kev. Cov tshuaj tiv thaiv no feem ntau pib nrog 5-nitroindole, uas yog tsim los ntawm tshuaj txo qis rau 5-aminoindole, thiab tom qab ntawd 5-iodoindole tau txais los ntawm kev kho 5-aminoindole nrog ntau tshaj iodine thiab hypochlorite. Txoj kev no yuav tsum tau siv cov kev sim ua tau zoo los xyuas kom meej qhov purity thiab tawm los ntawm cov synthesized 5-iodoindole.
5-IODOINDOLE yog cov khoom siv hluav taws xob feem ntau siv organic, thiab ib qho ntawm nws txoj kev npaj yog los ntawm Sandmeyer cov tshuaj tiv thaiv txoj kev. Txoj kev siv 5-IODOINDOLE raws li cov khoom siv raw thiab dhau los ua cov tshuaj tiv thaiv kab mob thaum kawg tau txais cov khoom lag luam.
Cov kauj ruam ntawm txoj kev tshuaj tiv thaiv Sandmeyer yog raws li hauv qab no:
(1.) Npaj reactants. Npaj reactants xws li 5-IODOINDOLE, tooj liab chloride, sodium chloride, nitrophenol thiab sulfuric acid.
(2.) Sib tov 5-IODOINDOLE nrog cov tshuaj. Ntxiv 5-IODOINDOLE rau cov tshuaj nrog sodium chloride thiab nitrophenol thiab do zoo kom sib tov.
(3.) Ntxiv tooj liab chloride. Ntxiv tooj liab chloride rau cov tshuaj tiv thaiv maj mam, thiab do zoo los txhawb cov tshuaj tiv thaiv.
(4.) Ntxiv sulfuric acid. Ntxiv sulfuric acid rau cov tshuaj tiv thaiv maj mam, thiab do zoo kom ceev cov tshuaj tiv thaiv.
(5.) Ntxiv sodium nitrite dropwise. Sodium nitrite tau maj mam ntxiv dropwise rau hauv cov tshuaj tiv thaiv thaum nplawm tas li kom txog thaum cov tshuaj tiv thaiv tiav.
(6.) Hloov cov tshuaj tiv thaiv. Cov tshuaj tiv thaiv tau hloov mus rau cov kua dej nag, thiab cov khoom tau los nag.
(7.) Lim. Cov khoom raug lim, ntxuav thiab qhuav kom thaum kawg tau lub hom phiaj khoom 5-nitro INDOLE.
Cov saum toj no yog Sandmeyer cov tshuaj tiv thaiv ntawm 5-IODOINDOLE thiab nws cov kauj ruam ntxaws.
2. Rau cyclization cov tshuaj tiv thaiv:
Siv txoj kev no, 5-iodoindol-2-yl-acetate tuaj yeem hloov mus rau 5-iodoindole los ntawm cua sov cov tshuaj tiv thaiv hauv carbon trichloride. Cov tshuaj tiv thaiv no yuav tsum muaj cov txheej txheem ntev ntev thiab xav tau cov tshuaj tshwj xeeb, uas yog cov kev txwv ntawm txoj kev no.
Cov kauj ruam tshwj xeeb yog raws li hauv qab no:
(1.) Ua ntej ntxiv ferric chloride thiab LiBr rau hauv acetonitrile qhuav thiab do. Tom qab ntawd 5-bromoindine thiab catalyst Pd(OAc)2 tau ntxiv thiab cov khoom sib tov tau rhaub rau 80 degree.
(2.) Los ntawm tsis tu ncua ntxiv N-methylbenzenesulfonamide thiab ua kom cov tshuaj tiv thaiv sib tov nyob rau hauv qhov kub ntawm 80 degree - 90 degree .
(3.) Tom qab ntawd cov tshuaj tiv thaiv sib tov tau txias rau hauv chav tsev kub thiab lim kom tau txais cov khoom lag luam phiaj xwm -5-IODOINDOLE.
(4.) Cov khoom tuaj yeem ua kom huv los ntawm kev ua kom huv huv xws li kev ua haujlwm siab ua kua chromatography (HPLC) lossis kem chromatography.
Nws yuav tsum tau muab sau tseg tias thaum lub sij hawm txheej txheem synthesis, nws yog ib qho tsim nyog yuav tsum tau ua tib zoo saib xyuas cov kev ua haujlwm ntawm kev nyab xeeb ntawm lub chaw soj nstuam thiab ua raws li cov cai tswj kev nyab xeeb hauv kev ua haujlwm hauv phau ntawv ua haujlwm kom ntseeg tau tias muaj kev nyab xeeb thiab raug ntawm kev sim tshuaj lom neeg.
3. Stille cov tshuaj tiv thaiv:
Cov tshuaj tiv thaiv Stille yog ib txoj hauv kev raws li cov tshuaj tiv thaiv nucleophilic aromatic hloov pauv, uas siv 5-bromoindole thiab tin yog ib txoj hauv kev rau kev npaj ntawm 5-iodoindole. Cov tshuaj tiv thaiv no qeeb qeeb, yuav tsum tau siv sijhawm ntev dua, thiab xav tau kev ntsuas ntxiv los xyuas kom meej tias cov tshuaj tiv thaiv ua haujlwm zoo.
Cov kauj ruam yog raws li nram no:
(1.) Synthesis ntawm phenyltin tebchaw: nyob rau hauv kev tiv thaiv ntawm nitrogen, react stearic acid nrog Sn (SnCl4) los tsim Sn (stearic acid) 4. Sn (stearate) 4 ces reacted nrog phenylmagnesium halide los tsim phenylphenyltinoxytin (Ph2Sn(O. Ph).
(2.) Synthesis of 5-IODOINDOLE: Hauv acetonitrile hnyav, react Indole nrog ethyl iodide los tsim 5-IODOINDOLE.
(3.) Cov kev mob tshwm sim: Raws li kev tiv thaiv ntawm nitrogen, react phenylphenyltin oxide, palladium catalyst thiab 5-IODOINDOLE, thiab anneal los tsim cov khoom lag luam.
(4.) Kev tsom xam cov qauv: siv cov tswv yim xws li nuclear magnetic resonance (NMR) thiab high-performance kua chromatography (HPLC) los ua cov qauv kev soj ntsuam thiab kuaj purity ntawm cov tshuaj tiv thaiv cov khoom.
(5.) Cov txiaj ntsig thiab kev sib tham: Cov khoom lag luam tau npaj los ntawm Stille cov tshuaj tiv thaiv ntawm 5-IODOINDOLE, thiab cov tshuaj tiv thaiv thiab cov qauv khoom raug tshuaj xyuas thiab sib tham, uas tau tsim lub hauv paus rau kev sib txuas ntawm cov txiaj ntsig zoo.
Hauv cov ntsiab lus, Stille cov tshuaj tiv thaiv ntawm 5-IODOINDOLE yog ib txoj kev siv tshuaj lom neeg zoo uas tuaj yeem siv los npaj ntau yam tseem ceeb ntawm cov organic tebchaw.
4. Sib xyaw Sandmeyer cov tshuaj tiv thaiv thiab Hiyama cov tshuaj tiv thaiv:
Cov tshuaj tiv thaiv Sandmeyer thiab cov tshuaj tiv thaiv Hiyama tau muab tso ua ke kom hnov mob 5-chloroindole nrog organotin reagent kom tau txais 5-iodoindole nyob rau hauv catalysis ntawm txhuas trichloride. Txoj hauv kev no yuav tsum muaj kev paub txog chemistry yooj yim los xyuas kom meej cov tshuaj tiv thaiv zoo thaum muab cov khoom lag luam ntshiab.
5-IODOINDOLE Sandmeyer Reaction thiab Hiyama Reaction Combined Method
Cov tshuaj tiv thaiv Sandmeyer yog ib qho tseem ceeb tshuaj tsw qab tshuaj, uas feem ntau yog siv los ua synthesize aryl nitrogen tebchaw los ntawm cov amino tebchaw, thiab HIyama cov tshuaj tiv thaiv yog cov tshuaj tiv thaiv rau cov synthesis ntawm carbon-silicon bonds los ntawm silicon-raws li reagents. Kev sib xyaw ua ke ntawm ob qhov kev cuam tshuam no tuaj yeem qhia cov neeg hloov pauv thiab cov pab pawg ua haujlwm silicon hauv aryl compounds. Cov kauj ruam ua kom muaj zog:
(1.) Kev npaj ntawm Diazonium ntsev: Ntxiv 5-IODOINDOLE rau cov tov tov ntawm tooj liab oxide thiab sodium chloride, ntxiv concentrated nitric acid dropwise, do ntawm kev kub ceev rau 10 feeb, ces maj mam ntxiv boric acid, do rau 5 feeb. Thaum kawg, cov tshuaj tau hloov mus rau pH 5.5 nrog 5 feem pua NaOH. Hauv qhov no, lub precipitate yog Diazonium ntsev.
(2.) Kev hloov pauv: ntxiv cov tshuaj tooj liab nitrate, thiab tom qab ntawd ntxiv cov tshuaj potassium chloride lossis ferrous chloride los hloov Diazonium ntsev rau hauv cov amino compound.
(3.) Hiyama cov tshuaj tiv thaiv nyob rau hauv alkaline tej yam kev mob: ntxiv TMS stannous chloride, ethanol, boric acid, tooj liab catalyst thiab TBAF los tsim loj molecular silicon-hloov tebchaw. Cov tshuaj tiv thaiv tau txais los ntawm kev rho tawm hauv kev sib xyaw ntawm chloroform thiab dej.
Tag nrho cov txheej txheem tshuaj tiv thaiv:
C8H6IN plus CuCl plus NaNO2plus HCl → 5-iodo-1H-indazole plus N2ntxiv H2O
C8H6IN plus CuCl plus NaNO2ntxiv H2O → 5-Iodo-1H-azoles
C8H6IN plus CuCl plus NaNO2ntxiv H3BO3→ 5-Aminoindazole
C7H7N3plus CuCl2ntxiv rau KCl → 5-chloroindazoles
5-chloroindazoles plus EtOH plus B2O3ntxiv CuCl → 5-alkoxyindazoles
5-alkoxyindazoles plus TMS-Cl plus Et3N → 5-alkoxyindazoles-SiMe3
Hauv cov ntsiab lus, 5-iodoindole tuaj yeem ua ke los ntawm ntau txoj hauv kev. Txoj kev xaiv twg yuav tsum tau txiav txim siab raws li kev kuaj mob, qib kev paub txog tshuaj lom neeg thiab cov kev xav tau ntawm cov tshuaj tiv thaiv.