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Otutu ihe omimi nke di n'uwa

Otutu ihe omimi nke di n'uwa

Heterocyclic ogige

Ngwurugwu heterocyclic, nke a makwaara dị ka mgbidi mgbanaka bụ isi nke nwere mkpụrụ nke abụọ dị iche iche dịka ndị òtù ya / mgbanaka. O nwere ike ịbụ na oghere ndị dị na Heterocyclic bụ ọtụtụ dịgasị iche iche na ọnụ ọgụgụ dị mkpa nke ezinụlọ nke ogige ogige.

N'agbanyeghị ọrụ na usoro, ihe ọ bụla carbocyclic compound nwere ike gbanwere dịka analogs hétérocyclic dị iche iche site na dochie otu ma ọ bụ karịa mkpụrụ ndụ mgbanaka carbon na ihe dị iche iche. N'ihi ya, heterocycles enyewo ikpo okwu maka mgbanwe nke nchọpụta na mpaghara dịgasị iche iche gụnyere ma ọ bụghị nanị na ọgwụ, ọgwụ, nyocha, na kemịkal organic nke heterocyclic ogige.

Ihe omuma atu nke heterocyclic ogige bu ihe otutu ogwu, oria acids, ihe ka ukwuu n'ime ihe eji emeputa ihe na ihe ndi ozo, na otutu ihe ndi ozo dika cellulose na ihe ndi ozo.

nhazi ọkwa

Ọ bụ ezie na ogige heterocyclic nwere ike ịbụ ogige ma ọ bụ ogige na-edozi ahụ, ọtụtụ nwere ọ dịkarịa ala otu carbon. A pụrụ ịkọwa ogige ndị a dị ka usoro ha dị na kọmputa. Ogige heterocyclic zuru oke na-akpa àgwà n'otu ụzọ ahụ dị ka ihe mgbaru ọsọ acyclic. N'ihi ya, tetrahydrofuran na piperidine bụ ndị ethers na amine ndị nwere profaịlụ na-agbanwe agbanwe.

Ya mere, nnyocha nke kemịterocyclic kemistry, ya mere, na-elekwasị anya karịsịa na ihe ndị a na-ejighị edozi na ngwa ngwa gụnyere ihe ndị a na-emeghị ka ọ bụrụ nke a na-emeghị ka ọ ghara ịdị na ya. Nke a gụnyere furan, pyrrole, thiophene, na pyridine. A na-ejikọta akụkụ ndị ọzọ nke heterocyclic ogige na benzene yiri mgbaaka, nke maka furan, pyrrole, thiophene, na pyridine bụ benzofuran, indole, benzothiophene, na quinoline, n'otu n'otu. Ọ bụrụ na ejiri abụọ benzene yiri mgbaaka, ihe a na-arụpụta na nnukwu ezinụlọ nke ogige, nke bụ dibenzofuran, carbazole, dibenzothiophene, na aridine. Enwere ike ịwa akwa yiri mgbaaka na-etinye aka na heteroatom na usoro pi, usoro a na-ejikọta.

Nkwadebe na mmeghachi omume

Ngwunye 3 dị na ya

Oghere Heterocyclic nwere atọ atọ dị na mgbanaka bụ ụzọ ntanye nzaghachi nke mgbanaka mgbanaka. A na-ejikarị ụbụrụ nke nwere otu heteroatom. Ndị nwere ọgwụgwọ abụọ na-eme, n'ozuzu ha dị ka ndị na-anọchite anya ha.

Oxiranes, nke a makwaara dị ka epoxides bụ ndị na-ejikarị 3-membered heterocycles. Oxiranes dị njikere site na-emeghachi omume peracids na alkenes, na ezi stereospecificity. Oxiranes bụ ndị na-arụ ọrụ karịa ndị na-emeghị ihe ọ bụla a na-ejighị aka ha na-eme nke ọma nke eriri elu nke 3-membered. Mmeghachi omume ndị ọzọ na-amalite site na ntinye nke nucleophilic na electrophilic bụ mgbanaka mmeghachi omume n'ozuzu.

Ihe mmeghachi omume dị otú a na-agụnye ihe ndị na-emepụta ọgwụ nitrogen bụ ihe ndị na-emepụta ọgwụ na nke mbụ bụ anticancer ọgwụ ọjọọ. Mgbachi mgbanaka dị ka nke anticancer na-emepụta mechlorethamine na-etolite ion aziridium n'etiti. Ndị na-emepụta mkpụrụ ndụ na-emepụta mkpụrụ ndụ nke na-emepụta mkpụrụ ndụ gụnyere mkpụrụ ndụ cancer site na mgbochi nke ntinye DNA ha. A na-ejikwa ọgwụ nitrogen mee ihe dị ka anticancer mmadụ.

Azụ aziridine na oxirane dị oké mkpa kemịkal ụlọ ọrụ mmepụta ihe. N'ihe dị ukwuu na-emepụta oxirane, a na-emezi ethylene na oxygen. Mmeghachi omume ahụ, bụ nke kachasị mma nke mgbaaka 3 ndị a, bụ na ha nwere ike ibuso ndị nnocleophilic ọgụ iji mepee mgbanaka ahụ dị ka egosipụtara n'okpuru:

Ndị kachasị ọnụ atọ heterocyclic ogige otu heteroatom gụnyere:

Eju Unsaturated
Thiirane (episulfides) Thiirene
Phosphirane Phosphirene
Epoxides (oxirane, ethylene oxide) Oxirene
Aziridine Azirine
Borirane Borirene

Ngwurugwu heterocyclic kachasị atọ na-ejikọta ya na heteroatoms abụọ na-agụnye Diaziridine dị ka mmịpụta zuru oke na Diazirine dị ka ihe na-enweghị ihe ọkpụkpụ nakwa dị ka Dioxirane na Oxaziridine.

Mgbaaka anọ

E gosipụtara ụzọ dị iche iche nke nkwadebe nke heterocycles nke 4 ka ejiri mee ihe na eserese dị n'okpuru. Usoro nke imeghachi ihe amine, thiol ma ọ bụ 3-halo na isi ya bụ ihe dị irè kama ọ na-emepụta mediocre. Mgbanwe na mkpochapu bụ ihe mmeghachi omume. Ọrụ ndị ọzọ nwekwara ike ịsọ mpi na mmeghachi omume.

N'ihe atụ nke mbụ, ịmegharị cyclization na oxirane na-esọrịta mpi mgbe niile, mana elu nucleophilicity dị elu karịsịa ma ọ bụrụ na mmadụ na-eji isi ike.

N'ihe nke abụọ, e guzobere ma azetidine na aziridine ga-ekwe omume, ma ọ bụ naanị nke ikpeazụ ahụ ka a hụrụ. Ihe nyochaa nke anọ na-egosi na ụzọ a maka usoro azetidine ga-arụ ọrụ nke ọma ma ọ bụrụ na enweghị asọmpi.

N'ihe atụ nke atọ, nhazi nhazi nke mkpụrụ na-egosi nhazi nke oxetane ma gbochie cyclization nke oxirane. N'ihe atụ 5 na 6, ihe nchọgharị Paterno-Buchi na-adabara ka e guzobere oxetane.

Ụzọ nke na-akwadebe XTUMX-membered yiri mgbaaka heterocycles

Mmeghachi omume

Mmeghachi omume nke 4-membered heterocyclic ogige na-egosiputa mmetụta nbibi nke mgbanaka. Ihe osise a na-egosi ụfọdụ ihe atụ. Acid-catalysis bụ ihe dị iche iche nke mmeghachi omume mmeghe dị iche iche nke egosipụtara na ihe atụ 1,2, na 3a. N'ihe mmeghachi omume 2 nke okpuru, sulfur na - enweta chlorination electrophilic nke na - eduga na nhazi chlorosulfonium n'etiti na ngbanwe nke ion chloride na - emeghe. Na mmeghachi omume 3b, a na-ahụkwa ike nucleophiles ka emeghe ether ahụ. Mmeghachi omume nke Beta-lactones nwere ike ime ma ọ bụ site na acid-catalyzed acyl mgbanwe dị ka a hụrụ na 4a. O nwekwara ike ime site na nryl-O rupture site nucleophiles dị ka 4b.

N'ihe nyocha 6 na-egosi ihe na-adọrọ mmasị nke ntinye nke ọbara nke ortho-ester. 6 na-emeghachi omume na-egosi Beta-lactam cleavage nke penicillin G nke na-akọwa mmeghachi omume acylation nke ọma nke usoro mgbagwoju anya.

Ihe atụ nke mmeghachi omume nke ogige heterocyclic 4-membered

Ihe kacha baa uru heterocyclic ogige ndị yiri mgbaaka 4 bụ usoro ọgwụ nje abụọ, cephalosporins, na penicillins. Usoro abụọ ahụ nwere mgbanaka azetidinone nke a makwaara dịka bọtịnụ Beta-lactam.
A na-enyocha ọtụtụ oxetanes dị ka antiviral, anticancer, ndị na-egbochi ndị na-egbu egbu, na ndị na-eme ihe nkwenye. N'aka nke ọzọ, oxetanones na-ejikarị arụ ọrụ ugbo dị ka nje bacteria, na-egbu egbu, na ihe ọkụkụ nakwa na ịmepụta polymer.
A na - achọta nne na nna na mmanụ aṅụ mgbe ihe ndị na - esi ísì ụtọ na - arụ ọrụ dị ka ihe na - esi ísì ụtọ maka ogige ndị Europe, ferrets, na minks. A na-eji ọgwụ dị iche iche eme ihe dị ka ndị na-egbu egbu ma na-arụ ọrụ na teepu, dị ka ndị na-emechi mmebi ígwè, na n'ichepụta ndị polymer.

Ngwakọta anọ nwere mgbaaka anọ nwere otu heteroatom

Heteroatom zuru oke

Heteroatom Eju Unsaturated
Sulfur Naanị Azete
Ogwu Oxetane Oxete
nitrogen Azetidine Azete

Ngwakọta anọ nwere mgbaaka anọ nwere ọgwụ abụọ

Heteroatom Eju Unsaturated
Sulfur Dithietane Dithiete
Ogwu Dioxetane Dioxete
nitrogen Diazetidine Diazete

Ejiri 5 mee ihe na otu heteroatom

Thiophene, furan, na pyrrole bụ ndị nne na nna na-emepụta ihe ndị dị na 5-membered rings heterocycles. Nke a bụ akụkụ ha:

Ihe ndị e mepụtara nke thiophene, furan, na pyrrole bụ thiophane, tetrahydrofuran, na pyrrolidine. A na-eme ka ogige bicyclic nke ụyọkọ thiophene, furan, ma ọ bụ pyrrole tinye na ụda benzene dịka benzothiophene, benzofuran, isoindole (ma ọ bụ indole).
Nitrogen heterocycle pyrrole na-emekarị na mmanụ osote nke a na-akpụ site na decomposition nke ndị na-edozi site na ikpo ọkụ siri ike. A na-achọta mgbaaka pyrrole na amino acid dịka hydroxyproline na proline nke bụ ihe dị iche iche nke protein dị iche iche na-anọ n'ọtụtụ dị elu na protein nke njikọ, tendon, akpụkpọ, na ọkpụkpụ na collagen.
A na-ahụ ihe ndị na-emepụta pyrrole na alkaloids. Nicotine bụ pyrrole nke a maara nke ọma na nke nwere alkaloid. Hemoglobin, myoglobin, Vitamin B12, na chlorophylls, ha nile na-esonye n'inwe anọ pyrrole na nnukwu mgbanaka nke a na-akpọ porphyrin, dị ka nke chlorophyll B gosipụtara n'okpuru.

A na-emepụta bọta pigment site na nkwonkwo nke mgbanaka porphyrine ma nwee agbụ ígwè 4 pyrrole.
Ịkwadebe ihe mgbanaka ntinye na 5-membered
Nkwado mmepụta nke furan nwetara dịka egosiri n'okpuru site n'ụzọ aldehyd, furfural, nke sitere na pentose nke nwere ihe ndị dị ka ọkacobs. E gosipụtara ihe yiri nke thiophene na pyrrole na nke abụọ nke usoro.
Ahịrị nke atọ nke nhazi otu na - egosiputa nkwadebe n'ozuzu nke thiophenes, pyrroles, furans si n'ọnọdụ 1,4-dicarbonyl. A malitela ọtụtụ mmeghachi omume ndị ọzọ na-eduga ná nhazi nke heterocycles a gbanwere n'ọnọdụ a. E gosipụtara ụzọ abụọ n'ime usoro ndị a na nke abụọ na nke atọ. Furan na-ebelata palladium-catalyzed hydrogenation ka tetrahydrofuran. Nke a na-emepụta cyclic ether bụ ihe dị oké ọnụ ahịa nke a na-apụghị ịtụgharị na 4-haloalkylsulfonates kamakwa 1,4-dihalobutanes nke a pụrụ iji kwadebe olulu na pyrrolidine.

Ngwakọta oghere ise ejiri otu heteroatom

Heteroatom Unsaturated Eju
Antimony Stibole Stibolane
arsenic Njikwa Arsolane
Bismuth Bismole Bismolane
boron Borole Borolane
nitrogen Pyrrole Pyrrolidine
Ogwu oghe Tetrahydrofuran

Ejiri 5 na-ejikọta na 2 heteroatoms

Ogige mgbanaka ise nke nwere 2 heteroatoms na ọ dịkarịa ala otu n'ime heteroatoms bụ Nitrogen, nke a maara dị ka azoles. Isothiazoles na thiazoles nwere nitrogen na sọlfọ atom na mgbanaka ahụ. A na-akpọ ogidi na etiti sulfur abụọ dị ka Dithiolanes.

Heteroatom Unsaturated (na nke ụfọdụ unsaturated) Eju
nitrogen

/ nitrogen

Pyrazole (Pyrazoline)

Imidazole (Imidazoline)

Pyrazolidine

Imidazolidine

Nitrogen / oxygen Isoxazole

Oxazoline (oxazole)

Isoxazolidine

oxazolidine

Nitrogen / sọlfọ Isothiazole

Thiazoline (Thiazole)

Isothiazolidine

Thiazolidine

Oxygen / oxygen Dioxolane
Sulfur / sọlfọ Dithiolane

Ụfọdụ pyrazoles na-eme n'ụzọ nkịtị. A na-akwado ogige nke klas a site na ịza 1,3-diketones na hydrazines. A na-eji ọtụtụ pyrazole synthetic synthetic dị ka ọgwụ na ejiji. Ha na-agụnye mmụba analgesic aminopyrine, phenybutazone jiri ọgwụgwọ ọrịa ogbu na nkwonkwo, eriri eriri na odo odo tartrazine, na ọtụtụ ihe ejiji na-eji agba foto dị ka ndị na-ahụ maka ndị mmadụ.

Ejiri 5 na-ejikọta na 3 heteroatoms

E nwekwara nnukwu ìgwè nke ogige mgbanaka ise nwere ma ọ dịkarịa ala 3 heteroatoms. Otu ihe atụ nke ogige dị otú ahụ bụ dithiazoles nke nwere nitrogen atom na sulfur abụọ.

Ejiri 6 mejupụtara ya na 1 heteroatom

Nomenclature eji mee ihe na monocyclic nitrogen-nwere 6-membered mgbanaka oghere dị n'okpuru ebe a. E gosipụtara ọnọdụ n'elu mgbanaka maka pyridine, mkpụrụ ọgụgụ Arabic ka mma akwụkwọ ozi Grik, ọ bụ ezie na a na-eji usoro abụọ ahụ eme ihe. Pyridones bụ ogige aromatic site n'ikike nke onyinye iji mee ka ndị na-emepụta ihe dị iche iche dị ka egosipụtara maka 4-pyridone.

Uzo abuo abuo ndi nwere ike ime ihe di iche iche na-eme ihe n 'okpuru, NAD (nke a na-akpọ coenzyme1) na NADP (nke a na-akpọ coenyme II), sitere na nicotinamide.
Ihe ka ọtụtụ n'ime alkaloids nwere ngwugwu piperidine ma ọ bụ pyridine, n'etiti ha piperine (bụ otu n'ime ihe nchịcha na-acha ọcha na ose) na nicotine. E gosipụtara ha ebe ha.

Pyridine bụ nke e si na coal tar ma ọ bụ ugbu a na - edozi ya site na amonia na tetrahydrofurfuryl mmanya bụ ihe dị oké mkpa na ihe mgbaze ji emepụta ihe ndị ọzọ. Vinylpyridines bụ nnukwu ihe eji emepụta plastik, na piperidine zuru ezu, pyridine dị ka chemical raw material na roba nhazi.

Pyridine bara uru

Anu pyridine nke ọgwụ na-agụnye ọrịa hydrazide isonicotinic (tuberculostat isoniazid), ọgwụ nje nje HIV-a maara dịka nevirapine, nicorandil - avasodilator eji ejiji angina, phenazopyridine-ureary-tract analgesic as well as anti-inflammatory sulfa drug. Diflufenican, clopyralid, paraquat, na diquat bụ ihe oriri pyridine ndị a na-eji eme ihe bụ ndị a na-eji agwọ ọrịa.

Ejiri 6 mee ihe na 2 ma ọ bụ karịa heteroatoms

Ejiri nọmba 3 monocyclic na-ejikọta ya na 2 nitrogen heteroatoms (diazines) na aha dị ka egosiri n'okpuru ebe a.

Maleic hydrazide bụ ihe ndị e ji pyridazine mee ihe dị ka osisi herbicide. Ụfọdụ pyrazines dị ka aspergillic acid na-eme n'ụzọ nkịtị. Nke a bụ akụkụ nke ogige ndị ahụ e kwuru n'elu:

Ngwongwo Pyrazine bụ akụkụ dị iche iche nke polycyclic ogige nke ụlọ ọrụ mmepụta ihe na nke dị mkpa. Ndị dị mkpa nke ezinụlọ pyrazine bụ phenazines, alloxazines, na pteridines. N'iji ọgwụ na ahụike, diazine kachasị mkpa bụ pyrimidines. Cytosine, thymine, na uracil bụ 3 nke bases 5 nucleotide nke bụ mkpụrụ ndụ mkpụrụ ndụ na RNA na DNA. N'okpuru ebe a bụ akụkụ ha:

Vitamin thiamin nwere mgbidi pyrimidine na mgbakwunye na ụlọ ọgwụ ndị na-emepụta sịntịtị gụnyere ịka nwa na-ejikarị ọgwụ ọjọọ eme ihe. Morpholine (tetrahydro nne na nna-1,4-oxazine) na-emepụta n'ọtụtụ buru ibu iji mee ihe dị ka fungicide, mmechi mmebi, na ihe mgbaze. A na-ahụkwa mgbanaka Morpholine na ọgwụ ndị na-agwọ ọrịa ọgwụ na-egbu egbu na ọgwụ ụfọdụ dị ka fenpropimorph na steroid. Nke a bụ usoro nhazi maka morpholine:

Ngwunye 7 dị na ya

Dị ka ụda olu na-amụba, ọtụtụ ogige ndị nwere ike nweta site na mgbanwe nke ọnọdụ, ụdị, na ọnụ ọgụgụ nke heteroatoms na-abawanye ụba. Otú ọ dị, kemịl nke heterocycles na ejiri 7 mechie ma ọ bụ karịa ka enweghi ihe mepụtara karịa nke 6 na 5-membered ring heterocyclic compound.
Oxepine na Azepine yiri mgbaaka bụ ihe dị mkpa nke dị iche iche na-emepụta ngwaahịa metabolic nke ụmụ mmiri na alkaloids. Akpụpụtara azepine mara dị ka caprolactam bụ nke a na-emepụta n'ụdị ahịa maka iji mepụta nylon-6 dịka etiti na mmepụta akpụkpọ anụ, ihe mkpuchi, na ihe nkiri.
Ogige heterocyclic 7 na abụọ ma ọ bụ otu nitrogen aturu na mgbanaka ha bụ mpaghara nke usoro a na-eji psychopharmaceuticals Prazepine (tricyclic antidepressant) na tranquilizer diazepam makwaara dị ka valium.

Ngwunye 8 dị na ya

Ihe atụ nke oghere heterocyclic na klas a na-agụnye azocane, oxocane, na thiocane na Nitrogen, oxygen, na sọlfọ bụ ndị heteroatoms dị iche iche. Ngwá ọrụ ha ndị na-adịghị edozi ahụ bụ azocine, oxocine, na thiocine n'otu n'otu.

Ngwunye 9 dị na ya

Ihe atụ nke oghere heterocyclic na klas a gụnyere azonane, oxonane, na thionane na Nitrogen, oxygen, na sọlfọ bụ ndị heteroatoms dị iche iche. Ihe ndị ha na-emeghị ka ha bụrụ ndị na-adịghị edozi ahụ bụ azonine, oxonine, na thionine.

Ojiji nke heterocyclic ogige

A na-eji usoro ọgwụgwọ eme ihe n'ọtụtụ ebe nke sayensị na nkà na ụzụ. Dị ka anyị hụlarị na mkparịta ụka anyị, ọtụtụ ọgwụ ọjọọ bụ ogige hétérocyclic.

References

Akwụkwọ IUPAC Gold, heterocyclic ogige. Njikọ:

WH Powell: Ntụle nke usoro Hantzsch-Widman toro ogologo nke Nomenclature maka Heteromonocycles, na: Appl App. Chem.1983, 55, 409-416;

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

O. Widman: Zur Nomenclatur der Verbindungen, welche Stickstoffkerne enthalten, na: J. Prakt. Chem. 1888, 38, 185-201;