Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preliminary work to the ring syntheses of porphyrins, etc. III. Several pyrrole compounds with amino groups and unsaturated side chains》. Authors are Fischer, H.; Zeile, Karl.The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Formula: C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C. A. 24, 5302. 2,4-Dimethyl-3-amino-5-carbethoxypyrrole (I) yields an Ac derivative, m. 201° (60% yield). With iso-AmNO2, I gives 90% of the diazonium chloride, decomposes at 173°; it is not completely decomposed by boiling with H2O for 1 hr.; continued boiling, especially with Cu powder, gives 2,4-dimethyl-5-carbethoxypyrrole, m. 125°. Hydrolysis of I with 10% NaOH gives 2,4-dimethyl-3-amino-5 carboxypyrrole (II), which begins to split off CO2 at 75°; Ac derivative, m. 203° (decomposition). 2,4-Dimethyl-3-aminopyrrole, m. 127°, results in about 50% yield by warming the moist II at 75°; Ac derivative, m. 205°. The bromination product of the Ac derivative of I, heated with H2O, gives nearly quant. bis(3-acetylamino-4-methyl-5-carbethoxy-2-dipyrryl)methane, m. 251°, crystallizing in different forms from EtOH, Ac2O and dilute AcOH. With HCO2H and Fe powder, this yields an amorphous 1,4,5,8-tetramethyl-2,3,6,7 tetraacetylaminoporphin. II, HCO2H and HBr, heated 2-3 min., give (2,4-di-methyl-3-aminopyrryl)-2′,4′-dimethyl-3′-aminopyrrolenyl)methene tri-HBr salt, decomps over 280°; from H2O it seps. as violet crystals, from HBr in yellow-red prisms; AcONa gives the mono-HBr salt, dark violet needles, m. 234°. 2,4-Dimethyl-3-(β-carboxy-vinyl)-5-carbethoxypyrrole (III) and NaOH with a little H2O, heated over a free flame for 2 hrs. and then dry-distilled, give dimethylpyrrole and (2,4-dimethylpyrryl)(2′,4′-dimethylpyrrolenyl)methene. MeNO2 adds to 2,4-dimethyl-3-(β-nitrovinyl)-5-carbethoxypyrrole, giving the compound C12H17O6N3, m. 180°. 2,4-Dimethyl-3-(β-dicyano-vinyl)-5-carbethoxypyrrole (IV) and Br give a perbromide, golden yellow, decomposed by H2O to a 2-bromomethyl derivative, m. 258°. IV, MeOH and Br give the 2-carbomethoxy derivative, m. 187°; saponification with 0.1 N NaOH by heating 12 hrs. at 85° gives 2.5-dicarboxy-3-formyl-4-methylpyrrole, does not m. 360°; the di-Me ester m. 180° (oxime, m. 221°; semicarbazone, m. 247°). IV and SO2Cl2 in Et2O, followed by hydrolysis with H2O, give the 2-carboxy derivative, does not m. 360°; similarly III gives the 2-carboxy derivative, m. 241°; the free acid has no m. p. The Me ester of III m. 150°. 2,4-Dimethyl-3-formyl-5-carbethoxypyrrole and SO2Cl2 give the 2-carboxy-3-chloro derivative, m. 260°. 2,4-Di-methyl-3,5-diformylpyrrole (V) and 2,4-dimethyl-3-acetylpyrrole with HBr-EtOH give (2,4-dimethyl-3-formylpyrryl)(2′,4′-dimethyl-3′-acetylpyrrolenyl)methene, m. 210°. V and cryptopyrrole give with HBr 5,5′,3,3′-tetramethyl-4-ethyl-4′-formylpyrromethene-HBr, thick prisms. 2,4-Dimethyl-5-carbethoxy-3-thioformylpyrrole, for which a method of preparation is given, gives with SO2Cl2 and H2O 4-methyl-3-formyl-2-carbethoxy-5-carboxylic acid-pyrrole, m. 169°; phenylhydrazone, yellow, m. 235°.

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Related Products of 1273-73-0. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Probing the tolerance of cucurbit[7]uril inclusion complexes to small structural changes in the guest. Author is Yi, Song; Li, Wei; Nieto, Daniel; Cuadrado, Isabel; Kaifer, Angel E..

The binding properties of the cucurbit[7]uril host with three structurally related ferrocene-containing guests, ferrocenyltrimethylammonium, ferrocenylmethyltrimethylammonium and ferrocenylethyltrimethylammonium, were studied using 1H NMR spectroscopy, mass spectrometry, voltammetry and computational methods. The exptl. and computational data indicate that the stability of the cucurbit[7]uril inclusion complexes is relatively insensitive to the number of methylenes connecting the trimethylammonium and the ferrocenyl groups, although some of their properties are affected in significant ways.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Biosynthesis of porphyrins and related macrocycles. Part 25. Synthesis of analogs of coproporphyrinogen-III and studies of their interaction with coproporphyrinogen-III oxidase from Euglena gracilis, the main research direction is coproporphyrinogen III analog preparation decarboxylation enzyme; oxidase coproporphyrinogen III Euglena substrate selectivity; protoporphyrinogen IX formation coproporphyrinogen III mechanism.Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

Coproporphyrinogen III analogs I [R = (CH2)3CO2H, R1 = (CH2)2CO2H; R = (CH2)2CO2H, R1 = (CH2)3CO2H, (CH2)2CO2Me; R = (CH2)2CO2Me, R1 = (CH2)2CO2H] (II-V, resp.) were prepared Coproporphyrinogen III oxidase from E. gracilis acted on III and IV, which have normal substituents on the A-ring, to generate a vinyl group on that ring. The enzyme has no effect on II and V, where the A-ring propionic acid group has been changed. The implications of this in the biosynthesis of protoporphyrinogen IX from coproporphyrinogen III are briefly discussed. Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1273-73-0, is researched, SMILESS is Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25, Molecular C10BrFeJournal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Efficient Two-Electron Reduction of Dioxygen to Hydrogen Peroxide with One-Electron Reductants with a Small Overpotential Catalyzed by a Cobalt Chlorin Complex, Author is Mase, Kentaro; Ohkubo, Kei; Fukuzumi, Shunichi, the main research direction is electron reduction oxygen hydrogen peroxide formation; reductant overpotential catalyzed cobalt chlorin complex.Category: thiazolidine.

A Co chlorin complex (CoII(Ch)) efficiently and selectively catalyzed two-electron reduction of dioxygen (O2) by 1-electron reductants (ferrocene derivatives) to produce H2O2 (H2O2) in the presence of HClO4 (HClO4) in benzonitrile (PhCN) at 298 K. The catalytic reactivity of CoII(Ch) was much higher than that of a Co porphyrin complex (CoII(OEP), OEP2- = octaethylporphyrin dianion), which is a typical porphyrinoid complex. The two-electron reduction of O2 by 1,1′-dibromoferrocene (Br2Fc) was catalyzed by CoII(Ch), whereas virtually no reduction of O2 occurred with CoII(OEP). CoII(Ch) is more stable than CoII(OEP), where the catalytic turnover number (TON) of the two-electron reduction of O2 catalyzed by CoII(Ch) exceeded 30000. The detailed kinetic studies revealed that the rate-determining step in the catalytic cycle is the proton-coupled electron transfer reduction of O2 with the protonated CoII(Ch) ([CoII(ChH)]+) that is produced by facile electron-transfer reduction of [CoIII(ChH)]2+ by ferrocene derivative in the presence of HClO4. The 1-electron-reduction potential of [CoIII(Ch)]+ was pos. shifted from 0.37 V (vs. SCE) to 0.48 V by the addition of HClO4 due to the protonation of [CoIII(Ch)]+. Such a pos. shift of [CoIII(Ch)]+ by protonation resulted in enhancement of the catalytic reactivity of [CoIII(ChH)]2+ for the two-electron reduction of O2 with a lower overpotential as compared with that of [CoIII(OEP)]+.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis and isomerization of 4-hydroxy-4-methyl-3-hepten-6-yn-2-yl-cyclopentadienylmanganese tricarbonyl》. Authors are Anisimov, K. N.; Kolobova, N. E.; Magomedov, G. K. I..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Formula: C10BrFe. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

cf. CA 61, 13336f. Propargyl bromide added in Et2O to Mg activated with HgCl2 gave a solution of the Grignard reagent which with 2-penten-4-on-2-ylcyclopentadienylmanganese tricarbonyl in 3 h. refluxing gave 81% I, b0.007 85-6°, n20D 1.5945, d20 1.2936; ir spectrum and uv spectrum shown. Heated with KHSO4 in vacuo to 100-20°, I gave 50% yellow 4-methyl-2,4-heptadien-6-on-2-ylcyclopentadienylmanganese tricarbonyl, b0.007 95-6°, 1.6112, 1.3030, also formed from I by heating in EtOH with HgSO4; ir spectrum shown. The ketone was unstable in air, but gave a red 2,4-dinitrophenylhydrazone, m. 156°.

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Synthetic Route of C10BrFe. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Enhanced Electron-Transfer Reactivity of Nonheme Manganese(IV)-Oxo Complexes by Binding Scandium Ions. Author is Yoon, Heejung; Lee, Yong-Min; Wu, Xiujuan; Cho, Kyung-Bin; Sarangi, Ritimukta; Nam, Wonwoo; Fukuzumi, Shunichi.

One and two scandium ions (Sc3+) are bound strongly to nonheme manganese(IV)-oxo complexes, [(N4Py)MnIV(O)]2+ (N4Py = N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine) and [(Bn-TPEN)MnIV(O)]2+ (Bn-TPEN = N-benzyl-N,N’,N’-tris(2-pyridylmethyl)-1,2-diaminoethane), to form MnIV(O)-(Sc3+)1 and MnIV(O)-(Sc3+)2 complexes, resp. The binding of Sc3+ ions to the MnIV(O) complexes was examined by spectroscopic methods as well as by DFT calculations The one-electron reduction potentials of the MnIV(O) complexes were markedly shifted to a pos. direction by binding of Sc3+ ions. Accordingly, rates of the electron transfer reactions of the MnIV(O) complexes were enhanced as much as 107-fold by binding of two Sc3+ ions. The driving force dependence of electron transfer from various electron donors to the MnIV(O) and MnIV(O)-(Sc3+)2 complexes was examined and analyzed in light of the Marcus theory of electron transfer to determine the reorganization energies of electron transfer. The smaller reorganization energies and much more pos. reduction potentials of the MnIV(O)-(Sc3+)2 complexes resulted in remarkable enhancement of the electron-transfer reactivity of the MnIV(O) complexes. Such a dramatic enhancement of the electron-transfer reactivity of the MnIV(O) complexes by binding of Sc3+ ions resulted in the change of mechanism in the sulfoxidation of thioanisoles by MnIV(O) complexes from a direct oxygen atom transfer pathway without metal ion binding to an electron-transfer pathway with binding of Sc3+ ions.

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SDS of cas: 15965-55-6. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Chloro-7-nitro-1H-benzo[d]imidazole, is researched, Molecular C7H4ClN3O2, CAS is 15965-55-6, about Benzimidazoles. II. Effect of benzene nucleus substituents on the nuclopphilic reactivity of some 2-chloro-benzimidazoles.

cf. CA 67: 64300p. An equimol. mixture of 4,2-R(H2N)C6H3NH2.2HCl, or 3,2-R(H2N)C6H3NH2.2HCl and urea, heated 20 min. at 160-80°, the reaction mixture extracted with hot 10% NaOH and the alk. solution acidified with HCl, precipitated known 5(6)-substituted- or 4(7)-substituted-2-benzimidazolones, resp., which (0.01 mole) with 0.07 mole POCl3 and a few drops of concentrated HCl, heated 3-4 hrs. at 160-70° in a sealed tube yielded the following I (R, m.p., and % yield given): 5(6)-NO2, 222-3°, -; 5(6)-Cl, 207-8°, 70; 5(6)-Me, 185-6°, 72; 5(6)-MeO, 170-1°, 40; 4(7)-NO2, 196-7°, 40; 4(7)-Cl, 187-8°, 70; 4(7)-Me, 141-2°, 50; 4(7)-MeO, 151-2°, 55. Kinetic studies on the nucleophilic reactivity of I, carried out with piperidine at 100°, indicated that the 2-Cl mobility increases when R is electron-withdrawing, and decreases when R is electron donor. A linear correlation was also found for the effect of the substituents on the reaction center with σmeta + σpara for the position 5(6) and σortho + σmeta for the 4(7)-position, resp.

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Formula: C9H13NO2. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Atropisomerism in monopyrroles. Author is Boiadjiev, Stefan E.; Lightner, David A..

As observed by NMR, iodopyrroles 1a and 1b (Et and Me 3,5-dimethyl-4-[(1′-iodo-2′,2′-dimethyl)propyl]pyrrole-2-carboxylate) and a variety of related derivatives with iodine replaced by methoxy 2, thiomethyl 3, acetic acid esters 4, propionic acid ester 5 or malonic esters 6 exhibit restricted rotation about the C(4)-C(1′) bond due to the bulky tert-Bu group and an ortho effect from the sterically crowded 3,5-dimethylpyrrole. Most of the compounds, which are members of the rare class of atropisomers due to restricted rotation about an sp3-sp2 C-C bond, undergo diastereomeric enrichment by preparative TLC and crystallization From dynamic NMR studies of the enriched diastereomers one can determine kinetic and thermodn. parameters associated with the atropisomerism, e.g., ΔG‡ ∼24 kcal/mol for 1 and 5 (313 K), ∼22 kcal/mol for 3 (273 K), and ∼25 kcal/mol for 6 (313 K) in C2D2Cl4 solvent.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole( cas:1428537-19-2 ) is researched.Related Products of 1428537-19-2.Allen, Jamie R.; Bahamonde, Ana; Furukawa, Yukino; Sigman, Matthew S. published the article 《Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction》 about this compound( cas:1428537-19-2 ) in Journal of the American Chemical Society. Keywords: indolylalkanal chemoselective enantioselective preparation; chemoselective enantioselective aza Wacker reaction allylic homoallylic alc indole; enantioselective alkylation indole allylic homoallylic alc palladium catalyst; stereochem mechanism aza Wacker reaction deuterated allylic alc indole. Let’s learn more about this compound (cas:1428537-19-2).

In the presence of Pd(MeCN)2(OTs)2 and a nonracemic pyridinyloxazoline, 3-substituted indoles such as 3-phenylindole underwent intermol., chemoselective, and enantioselective alkylation/aza-Wacker reactions with cis-allylic and cis-homoallylic alcs. such as (Z)-EtCH:CHCH2OH mediated by p-benzoquinone in 1,2-dichloroethane to yield nonracemic β- and γ-(1-indolyl)alkanals such as I; enamines generated under other conditions were not formed. The mechanism was studied using the reaction of a deuterium-labeled allylic alc.; the stereochem. of the product supported a syn amino-palladation mechanism for the reaction.

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Name: Bromoferrocene. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Electron transfer in mixed-valence 1′,6′-bis(triphenylmethyl)biferrocenium triiodide. Author is Dong, Teng Yuan; Hsu, Tsui Ling.

The 1′,6′-bis(triphenylmethyl)biferrocenium triiodide (I) was prepared The intramol. electron transfer rates in the solid state and in solution have been determined I gives a Moessbauer spectrum which reveals the presence of localized and delocalized species. An investigation of the energy and the line-shape of the intervalence transition band, permitted the calculation of the electron transfer rate in solution

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