ʻO ka hapanui o nā huahopili kūpono i ka Honua
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;