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ʻO ka pūnaewele hōkū

ʻO ka heterocyclic compound, iʻikeʻia hoʻi heʻano o keʻano o ke kāpili,ʻo ia ka mea i loaʻa nā pahu o nā meaʻokoʻaʻelua i mau lālā o nā apo pepeiao. ʻO ka pūpū o ka hua'ōlelo hōʻemi paha ka mea nui loa a me ka helu nui loa o kaʻohana o ka mea kanu.

Ma muli o ka hana a me ka hoʻolālā, hiki ke hoʻoliloʻia i kēlā me kēia kapokapona carbocyclic i nā like anaterocyclic heterocyclic ma ka hoʻololiʻana i hoʻokahi aʻoi aʻe paha o nā kinolima kalapona me kekahi mea'ē aʻe. ʻO ka hopena, ua hāʻawi nā heterocycles i kahi papahana no ke kālepaʻana i ka noiʻi ma nā wahi likeʻole, akāʻaʻole i kau palenaʻia i ka lāʻau lapaʻau, lāʻau lapaʻau, kānakali, a me ka māmā lāʻau o nā mea heterocyclic.

ʻO nā hiʻohiʻona nui o nā pūnaele heterocyclic he mau lāʻau lapaʻau, meaʻonika nucleic, ka hapa nui o nā mea'enehu a me nā mea maoli, a me ka hapanui o ka biomass e like me cellulose a me nā mea i pili.

Maluna

ʻOiai paha he pūʻona a me nā mea pāʻona paha ka pūnaewele heterocyclic,ʻoi aku ka nui o hoʻokahi carbon. Hiki ke hoʻokaʻawaleʻia kēia mau pūnaewele e like me kā lākou papahana uila. ʻO nā pūpū heterocyclic māmā e hana like i nā mea likeʻole me nā'ākiko. ʻO ka hopena,ʻo ka tetrahydrofuran a me ka piperidine, he mau'anamela maʻamau a me nā amine me nā pūnaewele kala i hoʻololiʻia.

No laila,ʻo ka noʻonoʻoʻana i nā kemikona heterocyclic, ke kau nui nei ia i nā huahana i hoʻopihaʻoleʻia a me nā noi komo i nā lima i weheʻoleʻia a me nā'āpanaʻeono mau. ʻO kēia mau mea he furan, pyrrole, thiophene, a me pyridine. ʻO ka hui nui o heterocyclic composite e pili ana i nā apo memele, no ka furan, pyrrole, thiophene, a me pyridine he benzofuran, indole, benzothiophene, a me quinoline. Inā hoʻokomoʻiaʻelua mau mīkini palekana, nā hopena i kekahiʻohana nui o ka pūhui,ʻo ia hoʻiʻo dibenzofuran, carbazole, dibenzothiophene, a me aridine. Hiki ke hoʻohālikeʻia nā mīkini i hoʻohuiʻoleʻia ma muli o ke komoʻana o ka heteroatoma ma ka pūnaha pi, pūnaehana paʻa.

Hoʻomākaukau a me nā hoʻoikaika

Nā'āpana 3-i hoʻopaʻaʻia

ʻO nā pūpili hua'ōlelo pākolu meʻekolu mau mana i loko o ke apo iʻoi aku keʻano o ka hoʻomeameaʻana mai ke kaumaha o ke apo. Hiki ke palekana nā kūkoho o hoʻokahi heteroatom. ʻO nā mea e loaʻa ai nā heteroatomsʻelua, e like me keʻano o nā kauā.

Oxiranes, i kapaʻia he epoxides nā mea he nui loa o ka 3-membered heterocycles. Hoʻomākaukauʻia nā'Oxiranes ma ka hanaʻana i nā mea likecids me nā'āliki, me ka hilinaʻi maikaʻi. Uaʻoi aku ka lōʻihi o nā'Oxiranes ma mua o nā kahe i hoʻopihaʻoleʻia e ka mahele kiʻekiʻe kiʻekiʻe o ka rings 3-membered. ʻO ka hoʻohui houʻana i nā hanana e hanaʻia ana e ka puka nucleophilic a me ka electrophilic o ke apo heʻano hopena maʻamau.

ʻO ka hopena o kēiaʻano ke kauʻia nei i loko o ka haukapila'okōlika 'hana hana pharmacological i loaʻa i waena o nā hua'ōlelo mua loa i hōʻoleʻia i ka lāʻau hōʻailona. ʻO ka paʻiʻana o ka pūmole intramolecular e like me keʻano o ka'āpana anticancer mechlorethamine ka mea i hoʻokumu i kahi ionic aziridum. Hoʻopili ka mea hana i nā meaola olaola e hoʻonui i nā pūnaewele e like me nā pūnake kanikau ma o ka hanaʻoleʻana i kā lākou hoʻopiʻi DNA. Ua hoʻohana pūʻia nō hoʻi nā mustard Nitrogen e like me keʻano o nā anticancer agents.

ʻO ka waiwai aziridine a me ka oxirane he mau mea kanuʻoihana kūmole nui. Ma ka hana nui o oxirane, hoʻopiʻi ponoʻia ka ethylene me ka oxygen. ʻO ka hopena o ka huakini,ʻo ia ka meaʻoi loa o kēia mau mīkini 3-membered,ʻo ia hoʻi he mea hiki iā lākou ke hoʻoukaʻia e nā mea hoʻohui nucleophilic e wehe i ke apo e like me ia i hōʻikeʻia i lalo nei:

ʻO ka mea maʻamau iʻekolu mau helu Heterocyclic composite me hoʻokahi helu heteroatoma:

Hoʻopiha	Hoʻoponoʻoleʻia
ʻO Thiirane (episulfides)	ʻO Thiirene
Kūlanawai	Phosphirene
'Epoxides (oxirane, ethylene oxide)	Oxirene
'Aziridine	'Amirine
ʻO Borirane	ʻO Borirene

ʻO ka pūʻulu heterocyclic i piha iʻekolu mau helu meʻelua mau heteroatoms,ʻo ia ka Diaziridine e like me ke kīkoho maeʻa a me Diazirine me he mea i hoʻohemoʻoleʻia me Dioxirane a me Oxaziridine.

Nā HoʻohuiʻEhā

ʻO nāʻano hana hoʻomākaukau o nā heterocycles 4 i hoʻopaʻaʻia ma ke kiʻikuhi i lalo nei. ʻO ke kaʻina o ka hanaʻana i ka amine, thiol a me 3-halo me kahi waihona e mana maoli nō naʻe akā me ka hua o mediocre. ʻO ka hoʻohālike a me ka hoʻokahuliʻia he mauʻano o keʻano. Hiki i nāʻoihana'ē aʻe ke paio ma ka hopena.

I ke kumu mua, ka hoʻokūkū o ka cyclization i kekahi oxirane i ka hoʻokumuʻana o ka thietane, akā,ʻoi aku ke kiʻekiʻe o ka nucleophilicity ma kahiʻoi aku o kahi mea palupalu.

Ma ka hanaʻelua, hiki ke hoʻokumuʻia o ka azetidine a me ka aziridine, akā,ʻikeʻia ka hope. Ke hōʻike i ka helu heluʻehā, he hana maikaʻi kēia e pili ana i ke kūkuluʻana i ka azetidine ināʻaʻole he hoʻokūkū.

I keʻanoʻekolu,ʻo ka hoʻonohonoho pono o ke pāpale i makemakeʻia e hoʻokumuʻia i ka oxetane a kāohi i ka cyclization o oxirane. Ma nā hiʻohiʻona 5 a me 6, pono ka paʻi kiʻiʻana o Paterno-Buchi i ka hanaʻana i ka mea oxetane.

Nā hana o ka hoʻomākaukauʻana i nā heterocyclesʻo 4-membered

Nā kū'ē

Nā kū'ē o 4-membered Heterocyclic composite hōʻike pū i ka mana o ke kāʻei. Hōʻikeʻia kēia mau hiʻohiʻona i kekahi mau hiʻohiʻona. ʻO ka Acid-catalyysis he hiʻohiʻona maʻamau o nā hāʻina o nā hāhā hāmama i hōʻikeʻia ma nā hiʻohiʻona 1,2, a me 3a. Ma ka pane 2 o ka thietane, e hoʻomalu ke sulfur i ka chlorination electrophilic e alakaʻi i ke kūkulu o ka chlorosulfonium waena a me ke paniʻana o ka ioni hoʻokiʻekiʻe hōkū. I ka hoʻoukaʻana o 3b,ʻikeʻia nā nucleophiles ikaika e wehe i kaʻala. Hiki i nā hoʻohālikelikeʻokiʻana o Beta-lactones ke hanaʻia e ka'āpana acyl-catalyzed acyl e like me ka mea iʻikeʻia ma 4a. Hiki ke hana ia ma o alkyl-O rupture e nā nucleophiles e like me 4b.

Hōʻike ka helu helu 6 i kahi hiʻona o ka mimiʻopoʻa o ka hoʻohui houʻana o ka ester. Hōʻike ka 6 i ka cleavage Beta-lactam o ka penicillin G e ho'ākāka ana i ka hoʻonuiʻiaʻana o ka hoʻoleleʻana o ka pūnaewele kaomi.

Nā hiʻohiʻona o nā hāʻina o ka pūʻali heterocyclic 4-membered

ʻO ka mea maikaʻi loa Heterocyclic composite me nā'āpana 4-memberedʻelua lālani o nā mea'alopelo, ka cephalosporins, a me ka penicillins. ʻO nā pūʻuluʻelua he azetidinone ringi ka mea i kapaʻiaʻo Beta-lactam.
Hoʻomalokaʻia he nui o nā oxetanes e like me nā antiviral, anticancer, anti-inflammatory, and antifungal agents. ʻO ka'oxetanones, ma kekahiʻaoʻao, he mea nui loa ia i ka mahiʻai e like me bactericides, fungicides, a me nā herbicides a me ka hanaʻana o ka polymer.
Uaʻikeʻia ka makua i keʻano o kaʻaila o ka'alela ma kona mau meaʻono e hana ai he mau mea hoʻonāukiʻu no nāʻeke Pākehā, nā momona, a me nā minks. Hoʻohanaʻia ka Thietanes e like me ka momona a me nā bactericides i loko o ka pena, e like me nā mea hōʻailona hao'āpana, a ma ka hanaʻana o nā polymers.

ʻO nā pūpūʻehā me ka hoʻokahi heteroatoma

Hoʻokūʻoleʻia ka Hīpīpī

Hōʻoia	Hoʻopiha	Hoʻoponoʻoleʻia
'o Sulusa	ʻO Thietane	ʻAiwa
Oxygen	'Oxetane	Oxete
Nitrogen	ʻO ka Azetidine	ʻAiwa

ʻO nā pūmāmāʻehā meʻelua mau heteroatoms

Hōʻoia	Hoʻopiha	Hoʻoponoʻoleʻia
'o Sulusa	ʻO Dithietane	ʻO Dithiete
Oxygen	ʻO Dioxetane	ʻO Dioxete
Nitrogen	ʻO Diazetidine	Diazete

5-me nā'āpana me ka heteroatoma hoʻokahi

ʻO Thiophene, furan, a pyrrole ka pūpū momona o nā mau heterocycles 5-membered. Eia ko lākou mau hale:

ʻO nā mea i loaʻa i ka thiophene, furan, a me pyrrole, he thiophane, tetrahydrofuran, a pyrrolidine. ʻO nā pūpū bicyclic i hanaʻia e ka thiophene, furan, aiʻole pyrrole ringi i hoʻokomoʻia i ke apo benzene, ua kapaʻiaʻo benzothiophene, benzofuran, isoindole (aiʻole indole).
ʻO ka hanana heterocycle Nitrogen keʻano maʻamau i kaʻaila o ka iwi i hanaʻia e ka decomposing o nā protein ma o ka hoʻomehanaʻana. Hoʻokumuʻia nā apo o ka pyrrole i loko o nā amino waikawa e like me hydroxyproline a me proline nāʻano o nā proteins'ē aʻe e noho nei ma nā kiʻekiʻe kiʻekiʻe i nā kumu hana o nā ligaments, nā tendons, kaʻili, a me nā iwi a me nā'ōpū.
Loaʻa nā huahana Pyrrole i loko o nā alkaloids. ʻO Nicotine ka pyrrole iʻike nuiʻia i loko o nā pāloid. Hemoglobin, myoglobin, Vitamin B12, a me nā chlorophylls, ua hanaʻia ma o ka hoʻohuiʻana i nāʻehaʻehāʻehā i loko o ka pōpona nui e kapaʻia he porphyrin, e like me ka mea o ka chlorophyll B i hōʻikeʻia i lalo nei.

Hoʻomumuʻia nā pēlelele i loko o ka'āpana o ka memeka porphyrin a loaʻa i ke kaula he mau mimiko 4 pyrrole.
Hoʻomākaukauʻana i nā heterocycles o nā kaha 5-membered
ʻO ka hoʻomākaukauʻana i ka ulu o ka furan i kaʻoihanaʻoihana e like me ka mea i hōʻikeʻia ma lalo ma ke ala o aldehyd, furfural, i hanaʻia mai ka pentose i loko o nā meaʻoi e like me corncobs. Hoʻohālikeʻia nāʻano likeʻole o ka thiophene a me pyrrole i ka lālaniʻelua o nā hoohalike.
ʻO ka lālaniʻekolu o ka hoʻohālike hoʻokahi e hōʻike ana i ka hoʻomākaukau nuiʻana i nā pani, pyrroles, furan mai nā pūnaewele 1,4-dicarbonyl. Ua hoʻomakaʻia nā kumuhana he nui e alakaʻi ai i ke kūkuluʻana i nāʻano o kēiaʻano. Ua hōʻikeʻiaʻelua o kēia mau hanana i ka hāʻinaʻelua a me kaʻekolu. Ua hoʻemiʻiaʻo Furan e ka palladium-catalyzed hydrogenation i ka tetrahydrofuran. He mea nui kēia e hoʻoheheʻeʻia ai kēia kalaika cyclic e hikiʻole ke hoʻohuliʻia i nā 4-haloalkylsulfonates akāʻo ka 1,4-dihalobutanes paha e hiki ke hoʻohanaʻia e hoʻomākaukau i ka thiolane a me pyrrolidine.

ʻO nā pūhui lima lima me ka hoʻokahi heteroatom

Hōʻoia	Hoʻoponoʻoleʻia	Hoʻopiha
ʻO Antimony	Wahi	Stibolane
Hoʻokena	Palepili	ʻO Arsolane
ʻO Bismuth	Kūmole	ʻO Bismolane
Boron	ʻO Borole	ʻO Borolane
Nitrogen	ʻO Pyrrole	ʻO Pyrrolidine
Oxygen	ʻO Furan	ʻO Tetrahydrofuran

Hanaʻia ka 5 me ka 2 heteroatoms

ʻO nā pūlima mele limaʻelima i loko o ka 2 heteroatoms a ma ka liʻiliʻi o hoʻokahi o nā heteroatoma he Nitrogen, i kapaʻia he azoles. ʻO ka Isothiazoles a me nā thiazoles heʻaila a me ka sulfur aia ma ke apo. ʻO nā pūpū me nā pūnia sulfur e kapaʻiaʻo Dithiolanes.

Hōʻoia	ʻAʻole i hoʻomaʻemaʻeʻia (a me ka pauʻole i hoʻomaʻemaʻeʻia)	Hoʻopiha
Nitrogen / nitrogen	Pyrazole (Pyrazoline) Imidazole (Imidazoline)	ʻO Pyrazolidine Imidazolidine
Nitrogen / oxygen	Ixaxazole 'Oxazoline (oxazole)	Isoxazolidine kaupona
Nitrogen / sulfur	Isothiazole Thiazoline (Thiazole)	ʻO Isothiazolidine ʻO Thiazolidine
ʻO oxygen / oxygen		ʻO Dioxolane
Sulfur / sulfur		ʻO Dithiolane

Kū i kekahi pyrazoles ma keʻano. Pono nā pūpū o kēia papa ma ka hanaʻana i nā 1,3-diketones me nā hydrazines. Hoʻohanaʻia ka nui o nā pyrazole pūpaʻa i lāʻau lapaʻau a me nā meaʻono. ʻO lākou me ka analgesic america aminopyrine lālā, ka phenybutazone i hoʻohanaʻia i ka hanaʻana o ka lāʻau, ka lapa ahi a me kaʻulaʻulaʻeleʻele o ka tartrazine, aʻo ka hapa nui o nā mea inu i hoʻohanaʻia i ke kiʻiʻulaʻula e like me nā mea leʻaleʻa.

Hanaʻia ka 5 me ka 3 heteroatoms

Loaʻa i kahi hui nui o nā pūlima lima lima mau me ka 3 heteroatoms ma lalo iki. ʻO kekahi o kēiaʻano pūnaewele he dithiazoles i loko o kaʻenehana nitrogen aʻelua sulfur.

Hanaʻia ka 6 me ka 1 heteroatom

ʻO ka inoa nomenclature i hoʻohanaʻia i loko o nā pūnaewele me nā 6-membered me ka monocyclic. Hōʻikeʻia nā wahi ma ke apo no pyridine, uaʻoi aku ka maikaʻi o nā helu'Anela i nā leka Helene,ʻoiai ua hoʻohanaʻia nā pūnaeweleʻelua. ʻO nā pyridones he'āpana pāʻona i ka hāʻawiʻia o nā kōkua i ka hoʻopunipuni i nā'ōpili mai nā papa hana resonance i hōʻikeʻia no ka 4-pyridone.

ʻElua mau lekenehu nui i komo i nāʻano hana likeʻole i loko o nā pūnaewele,ʻo NAD (ʻo ia hoʻi ka coenzyme1) a me ka NADP (ʻo ia hoʻi ka coenyme II), no ka nicotinamide.
ʻO ka hapanui o nā alkaloids he'ōpili piperidine a pyridine paha, i loko o lākou me ka piperine (kahi o nā meaʻonoʻoi aku o ka pepaʻeleʻele a me keʻokeʻo) a me ka nicotine. Hōʻikeʻia ko lākou mau hale i lalo nei.

ʻO Pyridine i lawe muaʻia mai ka wahī walaʻau akā ua hoʻomākaukau kokeʻiaʻo ia mai ka amonia a me ka waihā tetrahydrofurfuryl i ka mea waena a me ka mea pale e hoʻohanaʻia no ka hanaʻana i nā hui. ʻO Vinylpyridines nā mea kanu nui o ka pilapika, a me ka piperidine piha, ua hoʻohanaʻiaʻo pyridine e like me nā meaʻenehana me ka hana hoʻoponopono.

ʻO nā pyridine waiwai maikaʻi

ʻO nā pyridine huahua me nā meaʻai e komo pūʻia me ka hydrazide acid isonicotinic (tuberculostat isoniazid),ʻo ka lāʻau anti-AIDS-virus i kapaʻia he nevirapine, nicorandil - avasodilator hoʻohanaʻia no ka hoʻomaluʻana i angina, phenazopyridine-ʻo nā analaric urinary-tract a me ka lāʻau antifapalamaila anti-inflammatory. ʻO Diflufenican, clopyralid, paraquat, a me diquat he mau mea pyridine kaulana ia i hoʻohanaʻia me he mau lāʻau lapaʻau.

Hanaʻia ka 6 me ka 2 aʻoi aku heteroatoms

ʻO ka 3 monocyclicʻeono mau helu heterocycles me ka 2 nitrogen heteroatoms (diazines) helu a heluʻia e like me ka hōʻikeʻia i lalo.

ʻO Maleic hydrazide he mea paʻi pyridazine i hoʻohanaʻia me he herbicide. ʻO kekahi mau pyrazines e like me ka wai aspergillic e hana maoliʻia. Eia nā hale o ka mea i hōʻike muaʻia:

ʻO ka pahu Pyrazine kahi mea o nāʻano polycyclic polyvalent o kaʻoihana ahupuaʻa a me keʻano ola. ʻO nā lālā nui o kaʻohana pyrazine he phenazine, alloxazines, a me nā pteridine. ʻO ka pharmacologically a biologically,ʻo nā diazines nui loa he pyrimidines. ʻO Cytosine, thymine, a me uracil ka 3 o nā bases nucleotide 5 e lilo ana i ke genetic code i RNA a me DNA. Ma lalo iho ko lākou mau hale:

ʻO ka lāʻau Vitamin thiamin he kōpana pyrimidine a ma waho aʻe o nā barbiturates synthetic e pili pūʻia me ka amobarbital e hoʻohanaʻia i nā lāʻau lapaʻau. Hoʻopukaʻia ka Morpholine (tetrahydro-1,4-oxazine) ma ka laulā maʻamau no ka hoʻohanaʻana i he fungicide, he mea hoʻopunipuniʻino, a he mea pale. Hoʻokomo pūʻia ke apo Morpholine i loko o ka medetozine maʻamau a me kekahi mau momona e like me fenpropimorph a me shidemorph. Eia ke kumu hoʻohālikelike no ka morpholine:

Nā'āpana 7-i hoʻopaʻaʻia

I ka hoʻonuiʻana o ke apo, hiki ka nui o nā pūnaewele e hiki ke loaʻa ma o ka hoʻololiʻana i kahi, kahi, a me ka heluna o nā heteroatoms e piʻi nui. Eia nō naʻe, ke emiʻole ka māmā o nā heterocycles me nā memeu 7-membered aʻoi aʻe paha ma mua o ka pūnaewele heterocyclic a me ka 6 a me ka 5-membered ring.
ʻO nā'ōmaʻa o Oxepine a me Azepine nā mea koʻikoʻi o nāʻano likeʻole o ka hua iʻa o nā meaola moana a me nā alkaloids. ʻO ka'āpana azepine i kapaʻiaʻo caprolactam, kahi huahana kūʻaiʻia i loko o ka pūpū no ka hanaʻana i ka nylon-6 ma keʻano waena a me ka hanaʻana i nāʻiliʻili, nā'enehu, a me nā kiʻiʻoniʻoni.
Nā'āpana heterocyclic 7-membered meʻelua mau'enelamene ma loko o ko lākou apo he mau papahana o ka hoʻohanaʻana i nā kumuhana o Prazepine (tricyclic antidepressant) a me ka diazepam maikaʻi eʻikeʻia he valium.

Nā'āpana 8-i hoʻopaʻaʻia

ʻO nāʻano heterocyclic composite i loko o kēia papa,ʻo ia hoʻi nā azocana, oxocane, a me ka thiocane me ka Nitrogen, oxygen, a me ka sulfur,ʻo ia nā heteroatoms. ʻO kā lākou mau mea i hoʻohuiʻia i ka mea i hoʻopihaʻoleʻia he azocine, oxocine, a thiocine.

Nā'āpana 9-i hoʻopaʻaʻia

ʻO nāʻano heterocyclic composite i loko o kēia papa,ʻo ia nō ka azonane, ka oxonane, a me kaʻekolu a me ka Nitrogen, oxygen, a me ka sulfurʻo ia he heteroatoms. ʻO kā lākou mau mea i hoʻohuiʻia i ka hoʻohuiʻia he azonine, oxonine, a thionine.

Nā hoʻohana o ka pūpū heterocyclic

Hiki ke hoʻohanaʻia nā hua'ōlelo i nāʻano o kaʻike a me kaʻenehana. E like me kā mākou iʻike ai i loko o kā mākou kūkāʻana, he nui nā lāʻau lapaʻau heterocyclic.

E hoʻomaopopo '

ʻO'IUPAC Gold Book, heterocyclic composite. Link:

WH Powell: Ka nānā houʻana i ka pūnaewele Hantzsch-Widman i hoʻonuiʻia no ka Nomenclature no nā Heteromonocycles, ma: Pure Appl. ʻO Chem.1983, 55, 409-416;

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

O. Widman: Ka inoa o ka inoaʻo Verbindungen, ke kākoʻoʻo Stickstoffkerne enthalten, ma: J. Prakt. ʻO Chem. 1888, 38, 185-201;