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Tse ngata tsa Heterocycles tse Amehang Lefatšeng

Tse ngata tsa Heterocycles tse Amehang Lefatšeng

Lik'hamphani tsa Heterocyclic

Karolo ea heterocyclic, eo hape e tsejoang e le mohaho oa lesale ke motsoako o nang le liathomo tsa likarolo tse peli tse sa tšoaneng e le litho tsa moriri oa eona. Lik'hemik'hale tsa Heterocyclic e ka 'na ea e-ba tse ngata ka ho fetisisa le tse ngata ka ho fetisisa tsa lelapa la metsoako ea limela.

Ho sa tsotellehe tshebetso le ts'ebetso, sehlopha se seng le se seng sa carbocyclic se ka fetoha litšoantšo tse fapa-fapaneng tsa heterocyclic ka ho nkela liathomo tse le 'ngoe kapa tse ngata tsa carbon tse nang le karolo e fapaneng. Ka lebaka leo, li-heterocycle li fane ka sethaleng bakeng sa ho fapanyetsana lipatlisiso likarolong tse sa tšoaneng empa ho sa lekanyetsoe ho meriana, moriana, litlhahlobo le mekhoa ea tlhaho ea metsoako ea heterocyclic.

Mehlala e meholo ea metsoako ea heterocyclic ke lithethefatsi tse ngata, li-nucleic acid, boholo ba limela tsa tlhaho le tsa tlhaho, le bongata ba limela tse kang cellulose le thepa e amanang le eona.

tlhophiso

Le hoja lik'hemik'hale tsa heterocyclic e ka 'na ea e-ba li-organic kapa metsoako e mengata, boholo ba tsona li na le carbon e le' ngoe. Lihlopha tsena li ka aroloa ho latela mekhoa ea tsona ea elektronike. Lihlahisoa tsa heterocyclic tse khotsofatsang li phela ka tsela e tšoanang le lihlahisoa tsa acyclic. Ka lebaka leo, tetrahydrofuran le piperidine ke li-ethers tse tloaelehileng le li-amine tse nang le litlaleho tsa steric tse fetotsoeng.

Ka hona, ho ithuta ka k'hemistri ea heterocyclic, ho lebisitsoe haholo ka lihlahisoa tse sa sisinyeheng le lik'hamphani tse kenyelletsang li-rings tse hlano le lihlopha tse tšeletseng. Sena se kenyelletsa furan, pyrrole, thiophene, le pyridine. Sehlopha se latelang se seholo sa lik'hemik'hale tsa heterocyclic se kopanngoa le meketeng ea benzene, e leng bakeng sa furan, pyrrole, thiophene le pyridine ke benzofuran, indole, benzothiophene le quinoline ka ho latellana. Haeba lipalesa tse peli tsa benzene li kenngoa, sena se fella ka lelapa le leng le leholo la metsoako, e leng dibenzofuran, carbazole, dibenzothiophene, le aridine. Lihele tsa unsaturated li ka aroloa ka lebaka la karolo ea heteroatom ho tsamaiso ea pi, tsamaiso ea conjugated.

Litokisetso le liketso

Lihele tsa li-3

Heterocyclic e entsoeng ka liathomo tse tharo ka har'a lesale ke mokhoa o ts'oanelang ho itšehla thajana ka lebaka la khatello ea lesela. Heterocycles e nang le heteroatom e le 'ngoe e tsitsitse. Tse nang le heteroatom tse peli li etsahala, ka kakaretso e le li-intermediate tse itekanetseng.

Li-oxiranes, tse tsejoang hape e le lipoxide ke li-heterocycle tse nang le lihlopha tse ngata tsa 3. Li-oxirane li itokiselitsoe ka ho sebetsana le li-peracids tse nang le li-alkenes, tse nang le mekhoa e metle. Li-oxirane li sebetsa haholo ho feta li-ethers tse sa tsitsitseng tse nang le mekhabiso e phahameng ea sekhahla sa 3. Likarolo tsa ho eketsa tse tsamaisoang ke li-coreucleic le li-electrophilic tse bulehileng tsa lesale ke sehlopha se tloaelehileng se arabelang.

Mofuthu oa mofuta ona o kenngoa mofuteng oa lik'hemik'hale tsa moriana oa nitrogen o neng o le har'a lithethefatsi tsa pele tse hlahisang likokoanyana. Ho koala lesela la intramolecular joaloka mochine oa antichristine mechlorethamine o theha ion e ikhethang ea ioni. Sebopeho se sebetsang sa biologically se sebetsang se hlasela lisele tse ngata tse kenyang lisele tse nang le kankere ka ho thibela ho pheta-pheta ha tsona DNA. Li-nitrogen mosetareta li 'nile tsa sebelisoa e le mahlahana a anticancer.

Khoebo ea aziridine le oxirane ke lik'hemik'hale tse ngata tsa indasteri. Ka tlhahiso e kholo ea oxirane, ethylene e sebetsana ka ho toba le oksijene. Mokhoa oa lik'hemik'hale, e leng oona o khethollang ka ho fetisisa meketeng ena ea 3, ke hore li ka hlaseloa ke li-reagents tsa nucleophilic ho bula lesale joalokaha ho bontšitsoe ka tlaase:

Tse ling tse tharo ka ho fetisisa metsoako ea heterocyclic ka heteroatom e le 'ngoe e kenyeletsa:

E khotsofetse Unsaturated
Thiirane (episulfides) Thiirene
Phosphirane Phosphirene
Likokoana-hloko (oxirane, ethylene oxide) Oxirene
Aziridine Azione
Borirane Borirene

Mefuta e mengata ka ho fetisisa ea li-heterocyclic tse nang le lihlopha tse tharo tse nang le li-heteroatom tse peli li kenyelletsa Diaziridine e le ntho e nkiloeng ka matla le Diazirine e le motsoako o sa tsitsitsoeng hammoho le Dioxirane le Oxaziridine.

Lipina tse 'nè tse nang le litho

Mekhoa e fapaneng ea ho lokisa li-heterocycle tsa li-4 tse nang le lihlopha li bontšoa setšoantšong se ka tlaase. Mokhoa oa ho sebetsana le li-amine, lesholu kapa 3-halo e nang le motheo o atisa ho atleha empa ka lihlahisoa tse sa tloaelehang. Ho fokotsa matla le ho felisoa ke mokhoa o tloaelehileng oa liketso. Mesebetsi e meng e ka 'na ea boela ea hlōlisana ha e arabela.

Mohlala oa pele, cyclization ho oxirane e atisa ho phelisana le sebopeho sa thietane, empa li-nucleophilic e phahameng li laola haholo-holo haeba motho a sebelisa setsi se fokolang.

Mohlala oa bobeli, ho thehoa habeli azetidine le aziridine hoa khoneha, empa ho bonahala feela ho qetela. Mohlala palo ea bone e bontša hore mokhoa ona oa ho thehoa ha azetidine o sebetsa hantle haeba ho se na tlhōlisano.

Mohlala oa boraro, boits'oaro bo thata ba substrate bo rata ho thehoa ha oxetane 'me bo thibela cyclization ea oxirane. Mehlala ea 5 le 6, photocyclizations ea Paterno-Buchi e tšoanela haholo ho thehoa ha oxetane.

Mekhoa ea ho lokisetsa li-heterocycle tsa li-4 tsa lihlopha

Liketso

Liketso tsa litho tsa 4 metsoako ea heterocyclic e boetse e bonahatsa tšusumetso ea khatello ea kete. Setšoantšo se latelang se bontša mehlala e meng. Acid-catalysis ke ntho e tloaelehileng ea likarolo tse fapaneng tsa likarabo tse bontšitsoeng mehlaleng ea 1,2, le 3a. Ha e le hantle 2 ea thietane, sebabole e na le li-electrophilic chlorination tse lebisang tlhophisong ea chlorosulfonium lipakeng le ho kenngoa ha chloride ion. Ha li arabela 3b, li-nucleophiles tse matla li boetse li bonoa ho bula eher e thata. Liphetoho tsa cleavage tsa Beta-lactones li ka 'na tsa e-ba teng ka phapanyetsano ea acid-catalyzed acyl joalokaha e bone ho 4a. E ka boela ea etsoa ke al-O ho arohana ke li-nucleophile tse kang 4b.

Mohlala palo 6 e bonts'a ts'ebetso e thahasellisang ea ho tsosolosoa ha lipalesa tsa ortho-ester. Sepheo sa 6 se bontsa Beta-lactam cleavage ea penicillin G e hlalosang tsela e matlafatsang ea ho etsa li-acylation ea mokotlana oa lesakana.

Mehlala ea liketso tsa metsoako ea heterocyclic ea 4

E bohlokoa haholo metsoako ea heterocyclic le li-ring tsa 4 ke lihlopha tse peli tsa lithibela-mafu, cephalosporins le penicillin. Lihlooho tsena tse peli li na le reng ea azetidinone e tsejoang hape e le reng ea Beta-lactam.
Li-oxetane tse ngata li hlahlojoa e le likokoana-hloko, likokoana-hloko, li-anti-inflammatory, le mahlahana a maiketsetso. Li-oxetanone, ka lehlakoreng le leng, li sebelisoa haholo temo e le libtericides, fungicides, le likokoana-hloko le ha ho etsoa polymer.
Motsoali thietane o ile a fumanoa ka oli ea shale ha lihlahisoa tsa eona tsa odoriferous li sebetsa joaloka monko o monate oa li-polecats tsa Europe, ferrets le minks. Thietanes e sebelisoa e le li-fungicides le bactericides penteng, e le tšepe ea corrosion inhibitors le ho etsa lipolisi.

Lihele tse 'nè li entsoe ka heteroatom e le' ngoe

Heteroatom e Khotsofatswe le Unsaturated

Heteroatom E khotsofetse Unsaturated
Sebabole Thietane Azete
Oxyjene Oxetane Khofu
Nitrojene Azetidine Azete

Lihele tse 'nè li entsoe ka heteroatom tse peli

Heteroatom E khotsofetse Unsaturated
Sebabole Dithietane Dithiete
Oxyjene Dioxetane Dioxete
Nitrojene Diazetidine Diazete

Lihele tsa 5 tse nang le heteroatom e le 'ngoe

Thiophene, furan, le pyrrole ke motsoako oa motsoako o nkhang hamonate oa li-heterocycle tsa li-5. Mona ke mehaho ea bona:

Lihlahisoa tse phethehileng tsa thiophene, furan, le pyrrole ke thiophane, tetrahydrofuran, le pyrrolidine ka ho latellana. Lihlahisoa tsa bicyclic tse entsoeng ka lesale la thiophene, furan, kapa pyrrole tse kenngoeng ka keteng ea benzene li tsejoa e le benzothiophene, benzofuran, isoindole (kapa indole) ka ho latellana.
Manyolo a li-nitrogen heterocycle pyrrole a atisa ho hlaha ka oli ea bone e entsoeng ka ho qhibiliha ha liprotheine ka ho futhumala ho matla. Likhoele tsa pyrrole li fumanoa ka li-amino acid tse kang hydroxyproline le proline tse nang le likaroloana tsa liprotheine tse fapa-fapaneng tse nang le li-protein tse nang le li-ligamine, tendon, letlalo le masapo le collagen.
Lihlahisoa tse nang le li-pyrrole li fumanoa li-alkaloids. Nicotine ke pyrrole e tloaelehileng ka ho fetisisa e nang le alkaloid. Hemoglobin, myoglobin, Vithamine B12, le li-chlorophyll, kaofela ha tsona li thehoa ka ho kopanya li-unit tsa pyrrole tse ka hare ho lenaneo le leholo le bitsoang porphyrin, joaloka la chlorophyll B le bontšitsoeng ka tlaase.

Li-pigment tse hlahang li thehoa ka ho senyeha ha lesale la porphyrine 'me li na le ketane ea mehele ea 4 pyrrole.
Ho itokisetsa li-heterocycle tsa li-ring tsa 5
Ho etsoa lihlahisoa tsa li-furan ho ea ka tlaase mona ka tsela ea aldehyd, furfural, e hlahisitsoeng ke pentose e nang le lisebelisoa tse tala tse kang li-corncobs. Litokisetso tse tšoanang tsa thiophene le pyrrole li bonts'oa ka moleng oa bobeli oa equations.
Mokha oa boraro oa equation o bonts'a tlhahiso e tloaelehileng ea thiophenes, pyrroles, furans ho tloha 1,4-dicarbonyl metsoako. Liketsahalo tse ling tse ngata tse lebisang tlhophisong ea li-heterocycle tsa mofuta ona li qalile. Mekhoa e 'meli ea tsena e' nile ea bontšoa karolong ea bobeli le ea boraro. Furan e fokotsoe ke palladium-e nkiloeng ke hydrogenation ho tetrahydrofuran. E-ether ena ea li-cyclic is a solvent ea bohlokoa e ke keng ea fetoleloa feela ho 4-haloalkylsulfonate empa hape le 1,4-dihalobutanes e ka sebelisetsoang ho lokisa thiolane le pyrrolidine.

Lihele tse hlano li na le heteroatom e le 'ngoe

Heteroatom Unsaturated E khotsofetse
Antimony Tšoaea Stibolane
Arsenic Arsole Arsolane
Bismuth Bismole Bismolane
Boron Borole Borolane
Nitrojene Pyrrole Pyrrolidine
Oxyjene Furan Tetrahydrofuran

Li-ring tsa 5 tse nang le X -UMX heteroatom

Li-ring tse nang le lihlopha tse hlano tse nang le heteroatom tsa 2 le bonyane ho heteroatom e le 'ngoe ke metrogen, e tsejoang e le azoles. Li-isothiazoles le thiazoles li na le athomo ea naetrojene le sebabole kahare. Li entsoe ka liathomo tse peli tsa sulfur tse tsejoang e le Dithiolanes.

Heteroatom Unsaturated (le karolo e sa tsitsang) E khotsofetse
Nitrojene

/ naetrojene

Pyrazole (Pyrazoline)

Imidazole (Imidazoline)

Pyrazolidine

Imidazolidine

Nitrojene / oksijene Isoxazole

Oxazoline (oxazole)

Isoxazolidine

oxazolidine

Nitrojene / sebabole Isothiazole

Thiazoline (Thiazole)

Isothiazolidine

Thiazolidine

Oxyjene / oksijene Dioxolane
Sebabole / sebabole Dithiolane

Li-pyrazoles tse ling li hlaha ka tlhaho. Lik'hemik'hale tsa sehlopha sena li lokisetsoa ka ho itšoara ka 1,3-diketone ka hydrazines. Mefuta e mengata ea li-pyrazole e sebelisoa e le meriana le limela. Li akarelletsa ho fokotsa feberu ea aminopyrine ea feberu ea feberu, phenybutazone e sebelisoang kalafo ea ramatiki, dae ea fiber le 'mala oa mosehla oa tartrazine, le boholo ba li-color tse sebelisoang ka mebala ea lifoto e le mahlaseli a matlafatsang.

Li-ring tsa 5 tse nang le X -UMX heteroatom

Ho boetse ho e-na le sehlopha se seholo sa litho tsa lihlopha tse hlano tse nang le bonyane le 3 heteroatom. Mohlala o mong oa metsoako e joalo ke dithiazoles tse nang le atho ea naetrojene le libabole tse peli.

Li-ring tsa 6 tse nang le XHUMATHE hematatomane

Lebitso la nomenclature le sebelisitsoeng ka lik'hemik'hale tse nang le li-ring tsa 6 tse nang le li-nitrogen li ka tlase mona. Likarolo tse ka holimo tsa pyridine li bontšoa, lipalo tsa Searabia li khethoa haholo ho mangolo a Segerike, le hoja lisebelisoa tse peli li sebelisoa. Pyridones ke metsoako e nkhang hamonate e nang le menehelo ea ho hlahisa mefuta e sa tsoaneng le mefuta ea li-resonance e lefshoang joalokaha e bontšitsoe bakeng sa 4-pyridone.

Tse peli tse kholo tsa coenzymes tse kenang likarolong tse sa tšoaneng tsa ts'ebetso ea lik'hemik'hale ka lisele, NAD (e tsejoang hape e le coenzyme1) le NADP (e tsejoang hape e le coenyme II), e tsoa ho nicotinamide.
Boholo ba li-alkaloids bo na le mohaho oa piperidine kapa pyridine ring, har'a bona piperine (e hlahisa e 'ngoe ea lintho tse hlabosang ka ho fetisisa tsa pepere e ntšo le e tšoeu) le nicotine. Mehaho ea bona e bontšoa ka tlase.

Pyridine e kileng ea ntšoa ka 'mala oa mashala empa joale e lokiselitsoe catalytically ho tsoa ho ammonia le tetrahydrofurfuryl joala ke karolo ea bohlokoa le e sebelisetsoang ho hlahisa lik'hemik'hale tse ling. Vinylpyridines ke li-plastiki tse nang le monomoro oa bohlokoa, 'me piperidine e tletseng ka botlalo, pyridine e sebelisoa e le lik'hemik'hale le lisebelisoa tsa rabara.

Meriana e sebelisoang ka meriana

Meriana e sebelisoang ka meriana e akarelletsa isonicotinic acid hydrazide (tuberculostat isoniazid), lithethefatsi tse khahlanong le AIDS tse tsejoang e le nevirapine, nicorandil - avasodilator e sebelisetsoang ho laola angina, phenazopyridine-moriana oa metsoako ea urinary hammoho le lithethefatsi tsa sulfa tse khahlanong le ho ruruha. Diflufenican, clopyralid, paraquat, le diquat ke lintho tse tummeng tsa pyridine tse sebelisoang e le li-herbicides.

Lihele tsa 6 tse nang le 2 kapa heteroatom tse ling

Li-heterocycle tsa 3 tse nang le lihlopha tse tšeletseng tsa li-heterocycle tse nang le 2 nitrogen heteroatoms (diazines) li baloa ebile li bitsoa ka tlaase mona.

Maleic hydrazide ke motsoako oa pyridazine o sebelisoang e le herbicide. Li-pyrazines tse ling tse kang aspergillic acid li hlaha ka tlhaho. Mona ke mehaho ea lik'hemik'hale tse boletsoeng ka holimo:

Moriri oa Pyrazine ke karolo ea mefuta e sa tšoaneng ea polycyclic metsoako ea indasteri le ea bohlokoa. Litho tsa bohlokoa tsa lelapa la pyrazine ke phenazines, alloxazines, le pteridines. Pharmacologically le biologically, tse bohlokoa ka ho fetisisa diazines ke pyrimidines. Cytosine, thymine, le rracil ke 3 ea metheo ea 5 ea nucleotide e etsang liphatsa tsa lefutso ka RNA le DNA. Ka tlase mehaho ea bona:

Vithamine thiamin e na le lesale la pyrimidine 'me ho phaella ho li-barbiturate tse kenyelletsang li-amobarbital hangata li sebelisoa lithethefatsi. Morpholine (motsoali tetrahydro-1,4-oxazine) e hlahisoa ka bongata ho sebelisoa e le fungicide, corrosion inhibitor le solvent. Moriri oa morpholine o boetse o fumanoa ho trimetozine ea sedative-hypnotic and hypongitis e kang fenicpimorph le tridemorph. Mona ke moralo o hlophisitsoeng oa morpholine:

Lihele tsa li-7

Ha matla a reng ea reng e ntse e eketseha, mefuta e fapa-fapaneng ea metsoako e ka fumanoang ka ho fetola sebaka, mofuta le palo ea heteroatom e eketseha haholo. Leha ho le joalo, likhemik'hale tsa li-heterocycle tse nang le mehele ea 7 kapa tse ling ha li fokotsehe ho feta tsa 6 le 5-ring ring heterocyclic compounds.
Li-rings tsa Axpine le li-Azepine ke likarolo tsa bohlokoa tsa lihlahisoa tsa mefuta-futa ea tlhaho ea lik'hemik'hale tsa marine le li-alkaloids. Motsoako oa azepine o tsejoang e le caprolactam o hlahisoa ka bongata ka bongata bo sebelisoang ha ho etsoa nylon-6 e le bohareng le tlhahiso ea letlalo, liaparo le lifilimi.
Lik'hemik'hale tsa heterocyclic tse nang le 7 tse nang le athomo e 'meli kapa e le' ngoe ea nitrojene meleng ea tsona ke lihlopha tsa mekhoa ea psychopharmaceuticals Prazepine (tricyclic e thibelang ho imeloa kelellong) le tranquilizer diazepam e tsejoang hape e le valium.

Lihele tsa li-8

Mehlala ea metsoako ea heterocyclic sehlopheng sena e kenyelletsa azocane, oxocane, le thiocane le Nitrojene, oksijene le sulfure ke heteroatom e fapaneng. Lihlahisoa tsa tsona tse sa tsitsitsoeng li na le azocine, oxocine le thiocine ka ho latellana.

Lihele tsa li-9

Mehlala ea metsoako ea heterocyclic sehlopheng sena e kenyelletsa azonane, oxonane, le thionane e nang le naetrojene, oksijene le sulfure ke heteroatom e fapaneng. Li-derivatives tsa tsona tse sa tsitsitseng li na le azonine, oxonine le thionine ka ho latellana.

Mokhoa oa lik'hemik'hale tsa heterocyclic

Li-Heterocycle li thusa libakeng tse 'maloa tsa saense tsa bophelo le thekenoloji. Joalokaha re se re bone lipuisanong tsa rona, lithethefatsi tse ngata ke metsoako ea heterocyclic.

References

IUPAC Gold Book, metsoako ea heterocyclic. Khokahanyo:

WH Powell: Phetolelo ea Lenane la Nomenclature e fetisitsoeng ea Hantzsch-Widman bakeng sa Heteromonocycles, Ho: Appl e hloekileng. Chem.1983, 55, 409-416;

A. Hantzsch, JH Weber: Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe), Ho: Ber. Dtsch. Chem. Ges. 1887, 20, 3118-3132

O. Widman: Zur Nomenclatur der Verbindungen, käännös ja selenhoeken enthalten, Ho: J. Prakt. Chem. 1888, 38, 185-201;