Category: 2199-44-2

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 Dithiocarboxylic acids of pyrroles. II. Friedel-Crafts reactions with carbon disulfide. Author is Treibs, Alfred; Friess, Raimund.

Reaction of 2,4-dimethyl-5-(ethoxycarbonyl)pyrrole (I) with AlCl3 in CS2 gave 10% 3-(dithiocarboxy) derivative (II) of I. The same reactions in the presence of ClCO2Et gave the Et ester of II. 2-Methyl-3-(ethoxycarbonyl)pyrrole-5-dithiocarboxylic acid was obtained in 10% yield from 2-methyl-3-(ethoxycarbonyl)pyrrole with AlCl3 and CS2. These reactions show CS2 was not an indifferent solvent in Friedel-Crafts reactions.

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Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Structure-Activity Relationships of (4-Acylpyrrol-2-yl)alkanoic Acids as Inhibitors of the Cytosolic Phospholipase A2: Variation of the Substituents in Positions 1, 3, and 5. Author is Lehr, Matthias.

Derivatives of 3-(1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)propionic acid (1) and (1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)acetic acid (4) were prepared and evaluated for their ability to inhibit the cytosolic phospholipase A2 of intact bovine platelets. While replacement of one of the Me groups in position 1, 3, or 5 of the acetic acid 4 by a benzyl residue did not influence the inhibitory potency significantly, the introduction of a dodecyl chain led to compounds which even enhanced the enzymic activity. Stepwise elongation of the alkyl substituent in position 1 showed that the ability to inhibit the enzyme was lost when the alkyl chain exceeded a length of five carbons in case of compound 1 or six carbons in case of compound 4. Introduction of a polar functional group at the end of the 1-alkyl chain of these inactive pyrroles, however, restored or even elevated inhibitory potency. The most preferable of the polar terminal functions investigated was the carboxylic acid moiety. 6-[2-(2-Carboxyethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]hexanoic acid (65c) and 6-[2-(carboxymethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]nonanoic acid (66f) were to the synthesized inhibitors with the greatest potency. With IC50 values of 3.4 and 3.3 μM, resp., they were about 3-fold more active than the standard cPLA2 inhibitor arachidonyl trifluoromethyl ketone (IC50: 11 μM).

In some applications, this compound(2199-44-2)Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Kinetics of pyrrole substitutions. Iodination reaction》. Authors are Doak, Kenneth W.; Corwin, Alsoph H..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).Quality Control of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

The rates of iodination of 4 substituted pyrroles, measured in aqueous dioxane (28% dioxane by weight) at 26.5 ± 0.1°, follow 2nd-order equations. The substituents are methyl and carbethoxy groups. Reduction rates of 2 iodopyrroles with HI are also reported, one of which follows a 3rd order. From the data obtained it is shown that the α-position is about 25 times as reactive as the β-position. N-Methyl substitution increases the reactivity of the pyrrole ring 8 to 15% thus the effect is smaller than that of Me substitution on benzene. Similar studies of the reduction rates show the α-position to be 20 times as reactive towards reduction as the β-position. The iodination equilibrium constant K = [RI] [HSolv+] [I-]/[RH] [Solv] [I2], assuming the solvent as 48.2 M, is 24 for α-iodination and 21 for β-iodination, thus apparently little affected by structural changes.

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Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. 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 Chemistry of pyrrole pigments. III. Nitrogen-hydrogen tautomerism of substituted pyrromethenes. Proton nuclear magnetic resonance spectrometric investigations. Author is Falk, H.; Gergely, S.; Hofer, O..

The temperature-, solvent-, and concentration-dependence of the NMR of the pyrromethenes(I thru VI) was examined and the chem. shifts were assigned and the long range coupling constants were determined Intra- and intermol. proton transfer was observed; tautomeric NH exchanges at -100° were too fast to be measured by NMR.

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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: 2199-44-2, is researched, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2Journal, Justus Liebigs Annalen der Chemie called Dithiocarboxylic acids of pyrroles. II. Friedel-Crafts reactions with carbon disulfide, Author is Treibs, Alfred; Friess, Raimund, the main research direction is pyrrole dithiocarboxylic acid preparation; dithiocarboxylic acid pyrrole preparation; Friedel Crafts reaction carbon disulfide; carbon disulfide Friedel Crafts reaction.Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

Reaction of 2,4-dimethyl-5-(ethoxycarbonyl)pyrrole (I) with AlCl3 in CS2 gave 10% 3-(dithiocarboxy) derivative (II) of I. The same reactions in the presence of ClCO2Et gave the Et ester of II. 2-Methyl-3-(ethoxycarbonyl)pyrrole-5-dithiocarboxylic acid was obtained in 10% yield from 2-methyl-3-(ethoxycarbonyl)pyrrole with AlCl3 and CS2. These reactions show CS2 was not an indifferent solvent in Friedel-Crafts reactions.

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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 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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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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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A new pyrrole synthesis》. Authors are Fischer, Hans; Fink, Emmy.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).Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

Mutual reduction of isonitrosoacetoacetic ester or isonitrosobutyryl-acetic ester and AcCH2CH(OEt)2 (I) in the presence of Zn dust yielded 2-methyl-5-carbethoxypyrrole (II), m. 100°, subliming at 90° at 20 mm. On treatment with HCN and HCl in ether, II was converted to 2-methyl-5-carbethoxy-3-pyrrolecarboxaldehyde, m. 119°. I, heated with glacial AcOH for 1/2 h., yielded triacetylbenzene (III), m. 161°. In cold glacial AcOH, III was formed in only minimal amounts from I, but in considerable amounts from the Na salt of formylacetone. Acetylacetone was condensed with isonitrosoacetoacetic ester to form 2,4-dimethyl-3-acetyl-5-carbethoxypyrrole, and as a side-product, 2,4-dimethyl-5-carbethoxypyrrole, m. 123°. Glycine was condensed with AcCH2CHO, or with I, or with the Na salt of formylacetone, to yield a product, not yet isolated, giving a pos. Ehrlich reaction for pyrrole. These syntheses may be of physiol. importance in the formation of blood pigments.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis of cyanopyrroles, published in 1999-01-31, which mentions a compound: 2199-44-2, mainly applied to cyanopyrrole preparation; pyrrolenitrile preparation; oximinocyanoacetate diketone Knorr reductive condensation, Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

Regioselective synthesis of α-cyanopyrroles (vs. α-alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, HON:C(CN)CO2Me was reacted with CH2Ac2 in hot AcOH in the presence of Zn dust to give exclusively 3,5-dimethylpyrrole-2-carbonitrile when the AcOH was wet. Whereas, in glacial AcOH, only Me 3,5-dimethylpyrrole-2-carboxylate was isolated in ∼40% yield.

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