Category: 2199-44-2

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Analytical Chemistry called Automated Microflow NMR: Routine Analysis of Five-Microliter Samples, Author is Jansma, Ariane; Chuan, Tiffany; Albrecht, Robert W.; Olson, Dean L.; Peck, Timothy L.; Geierstanger, Bernhard H., which mentions a compound: 2199-44-2, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2, Computed Properties of C9H13NO2.

A microflow CapNMR probe double-tuned for 1H and 13C was installed on a 400-MHz NMR spectrometer and interfaced to an automated liquid handler. Individual samples dissolved in DMSO-d6 are submitted for NMR anal. in vials containing as little as 10 μL of sample. Sets of samples are submitted in a low-volume 384-well plate. Of the 10 μL of sample per well, as with vials, 5 μL is injected into the microflow NMR probe for anal. For quality control of chem. libraries, 1D NMR spectra are acquired under full automation from 384-well plates on as many as 130 compounds within 24 h using 128 scans per spectrum and a sample-to-sample cycle time of ∼11 min. Because of the low volume requirements and high mass sensitivity of the microflow NMR system, 30 nmol of a typical small mol. is sufficient to obtain high-quality, well-resolved, 1D proton or 2D COSY NMR spectra in ∼6 or 20 min of data acquisition time per experiment, resp. Implementation of pulse programs with automated solvent peak identification and suppression allow for reliable data collection, even for samples submitted in fully protonated DMSO. The automated microflow NMR system is controlled and monitored using web-based software.

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Product Details of 2199-44-2. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Deacylation and deformylation of pyrroles.

3-Acetyl- and 3-formyl-pyrroles are smoothly deacylated using either ethanedithiol/BF3 or (more conveniently) ethylene or neopentyl glycols in presence of p-MeC6H4SO3H. The reaction does not proceed when the acetyl or formyl group is in the 2-position, and in these cases the corresponding ketal or acetal is isolated. A mechanism for the deacylation process is proposed and is confirmed by deacylation of a pyrrole I bearing a cyclopentanone ring; under these circumstances the cleaved group is retained in the pyrrole II, and is identified.

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COA of Formula: C9H13NO2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about The reaction of β-aminoenones with α-amino derivatives. Synthesis of 2-functionalized pyrroles. Author is Alberola, Angel; Andres, Jose M.; Gonzalez, Alfonso; Pedrosa, Rafael; Vicente, Martina.

β-Aminoenones react with Et glycinate, α-aminoacetonitrile and α-aminoacetamide hydrochlorides leading to 2-functionalized pyrroles. Although the transamination is a high-yield process, the transformation of the intermediate, in both basic or thermally induced conditions, affords the corresponding pyrroles in poor to moderate yields. Thus, transamination of AcCH:CMeNH2 with EtO2CCH2N+H3 in MeOH gave 89% AcCH:CMeNHCH2CO2Et which on cyclization in EtONa/EtOH gave 33% Et 3,5-dimethyl-2-pyrrolecarboxylate.

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Formula: C9H13NO2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Pyrrole studies. XXX. A critical evaluation of the Knorr synthesis of trifluoromethylpyrroles and the reactivity of diethyl 4-trifluoromethyl-2-methylpyrrole-3,5-dicarboxylate. Author is Jones, R. Alan; Rustidge, David C.; Cushman, Susan M..

Pyrroles I (R = CO2Et, COMe) were prepared from F3CCOCH2CO2Et (II) and MeCOCH2R. II was nitrosated in HOAc, the mixture was refluxed, MeCOCH2CO2Et was added, Zn dust was introduced, and the new mixture was refluxed to give I (R = CO2Et). The nitrosation of MeCOCH2CO2Me and treatment of the product with II and Zn gave pyrrole III.

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Category: thiazolidine. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Pyrroles with isoprenoid substituents.

Pyrroles I (R1 = CO2Et, R2 = Me, CHO; R1 = I, R2 = CHO, 4,4,6-trimethyl-m-dioxan-2-yl; R1 = H, R2 = CHO) were prepared in 53-92% yield, e.g., acylation of 2,4-dimethyl-5-carbiethoxypyrrole with Me[MeCHCH2CH2CH2]3COCl gave 53% I (R1 = CO2Et, R2 = Me) (II). Treatment of II with NaBH4 gave 96% III [R1 = CH(OH)(CH2CH2CH2CHMe)3Me], which was dehydrated to give 93% III [R1 = CH:CH(CH2CH2CHMeCH2)3H]. III [R1 = CH2CH2(CH2CH2CHMeCH2)3H, CCl:CH(CH2CH2CHMeCH2)3H, CC(CH2CH2CHMeCH2)3H] were also prepared

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Some transformations of 2,4-dimethylpyrrole, published in 1923, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

From 0.9 g. 2,4-dimethylpyrrole (I) and 0.8 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 1 day is obtained 0.7 g. of the ketimine, m. 100°, sublimes 100° (HCl salt, green needles), of 2,4-dimethyl-5-acetylpyrrole (II). The ketimine is reduced by H and Pt sponge in alc. to I and when boiled with H2O to disappearance of the NH3 odor, 0.7 g. of it gives 0.3 g. II, m. 121°. 2,4-Dimethyl-5-chloroacetylpyrrole (0.9 g. from 1 g. I and 1 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 0.5 hr. in ice), m. 143°, gives in alc. with 30% NHMe2 after 0.5 hr. at 100° the 5-dimethylaminoacetyl derivative, m. 110°, while 0.5 g. boiled 0.5 min. in alc. with 40% HCHO and a few drops concentrated HCl yields 0.4 g. bis-[2,4-dimethyl-5-chloroacetylpyrryl]methane, m. 258°, which with NHMe2 in alc. gives the bis-5-dimethylaminoacetyl derivative m. 170°. I (1 g.) boiled up several times with 2 g. of 90% HCO2H and 10 drops of 20% HClO4 and allowed to stand 1 day gives 0.5 g. of the perchlorate, becomes discolored 200°, does not m. 260°, of bis-[2,4-dimethyl-pyrryl]methene, yellow, m. 117°. 2,4-Dimethyl-5-carbethoxypyrrole (III), obtained in 60-70% yield from I and EtMgBr and subsequent treatment with ClCO2Et, m. 125°, gives a positive Ehrlich aldehyde reaction in the cold, is hydrolyzed by boiling 50% KOH to the free acid, m. 136°, also obtained from the above Grignard compound with CO2. 2,4-Dimethyl-5-carbethoxypyrrole-3-aldehyde (IV). obtained in 85% yield from III and HCN in cold Et2O saturated with dry HCl and subsequent decomposition of the resulting imide chloride with hot H2O, m. 145°, gives a faint Ehrlich aldehyde reaction in the cold, more strongly on heating; 3 g. heated with 1:1 KOH until completely dissolved (about 15 min.) gives 2.2 g. of the free 5-carboxyaldehyde, m. 230°, which on distillation in vacuo yields 2,4-dimethylpyrrole-3-aldehyde, m. 126°, gives a positive aldehyde reaction even in the cold. Phenylhydrazone of IV, m. 204°. Azlactone, C19H18O4N2 (1.3 g. from 1.2 g. IV, 1.8 g. hippuric acid, 2.2 g. NaOAc and 20 cc. Ac2O heated 35 min. on the H2O bath), m. 232°. Oxime, m. 196-7°, converted by boiling NaOAc-Ac2O into the nitrile, C10H12O2N2, m. 171°. Semicarbazone, m. 285° (decomposition), converted by Na in alc. after 8 hrs. at 160-70° into 2,3,4-trimethylpyrrole. 2,4-Dimethyl-5-carbethoxy-3-chloroacetylpyrrole, from III and ClCH2CN, m. 163°, gives a faint positive Ehrlich reaction on heating, is highly sternutatory when powdered, gives in boiling alc. with aqueous KCN the 3-cyanoacetyl derivative, m. 172-3°.

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Category: thiazolidine. 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 Pyrroles with isoprenoid substituents. Author is Nizhnik, A. N.; Mironov, A. F..

Pyrroles I (R1 = CO2Et, R2 = Me, CHO; R1 = I, R2 = CHO, 4,4,6-trimethyl-m-dioxan-2-yl; R1 = H, R2 = CHO) were prepared in 53-92% yield, e.g., acylation of 2,4-dimethyl-5-carbiethoxypyrrole with Me[MeCHCH2CH2CH2]3COCl gave 53% I (R1 = CO2Et, R2 = Me) (II). Treatment of II with NaBH4 gave 96% III [R1 = CH(OH)(CH2CH2CH2CHMe)3Me], which was dehydrated to give 93% III [R1 = CH:CH(CH2CH2CHMeCH2)3H]. III [R1 = CH2CH2(CH2CH2CHMeCH2)3H, CCl:CH(CH2CH2CHMeCH2)3H, CC(CH2CH2CHMeCH2)3H] were also prepared

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Characterization, chemical optimization and anti-tumor activity of a tubulin poison identified by a p53-based phenotypic screen.Category: thiazolidine.

A robust p53 cell-based assay that exploits p53’s function as a transcription factor was used to screen a small mol. library and identify bioactive small mols. with potential antitumor activity. Unexpectedly, the majority of the highest ranking hit compounds from this screen arrest cells in mitosis and most of them impair polymerization of tubulin in cells and in vitro. One of these novel compounds, JJ78:1, was subjected to structure-activity relationship studies and optimized leading to the identification of JJ78:12. This mol. is significantly more potent than the original hit JJ78:1, as it is active in cells at two-digit nanomolar concentrations and shows clear antitumor activity in a mouse xenograft model as a single agent. The effects of nocodazole, a well established tubulin poison, and JJ78:12 on p53 levels are remarkably similar, supporting that tubulin depolymerization is the main mechanism by which JJ78:12 treatment leads to p53 activation in cells. In summary, these results identify JJ78:12 as a potential cancer therapeutic, demonstrate that screening for activators of p53 in a cell-based assay is an effective way to identify inhibitors of mitosis progression and highlights p53’s sensitivity to alterations during mitosis.

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Recommanded Product: 2199-44-2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis of cyanopyrroles. Author is Cheng, Ling Jiang; Lightner, David A..

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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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of pyrrolecarboxaldehydes》. Authors are Ghigi, Elisa; Drusiani, Annamaria.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).Computed Properties of C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

HCO-NMe2 (I) (23.89 g.) and 58.25 g. POCl3 warmed after 10 min. to 60°, treated dropwise in 1.5 hrs. with 18 g. 2,4-dimethylpyrrole in an equal volume of I, the mixture stirred 1 hr. at 60°, poured into 333 g. ice and 245 g. fused NaOAc, the mixture boiled, cooled, extracted with Et2O, the extract evaporated free from Et2O and made alk. with powd. Na2CO3, filtered, and the residual product (II) dried. Further extraction of the filtrate with Et2O gave another 0.69 g. II. II boiled in petr. ether, the solution purified with C, filtered and cooled gave 0.6 g. (crude) 2,4-dimethyl-3,5-pyrroledicarboxaldehyde, m. 165-6° (from H2O), and 9.6 g. (crude) 2,4-dimethyl-5-pyrrolecarboxaldehyde, m. 89-90° (from H2O). Similarly, I and POCl3 at 60°, treated dropwise with stirring with 2,4-dimethyl-8-ethylpyrrole gave 2,4-dimethyl-3-ethyl-5-pyrrolecarboxaldehyde, m. 105-6°. In the same way, 1.79 g. I and 4.37 g. POCl3 treated with 1.35 g. 2,3,4-trimethylpyrrole gave 0.3 g. 2,3,4-trimethyl-5-pyrrolecarboxaldehyde, m. 147°; 2.6 g. I and 6.32 g. POCl3 with 3 g. Et 2,4-dimethyl-3-pyrrolecarboxylate in I yielded Et 2,4-dimethyl-5-formyl-3-pyrrolecarboxylate, m. 165°; 8.6 g. I and 21 g. POCl3 with 10 g. Et 2,4-dimethyl-5-pyrrolecarboxylate and 10 g. I produced 11.2 g. Et 2,4-dimethyl-3-formyl-5-pyrrolecarboxylate, m. 145°. Heating 20 g. 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylate at 200° with 200 g. quinoline and 2 g. finely divided pure Cu to cessation of CO2 evolution, cooling, filtering, acidifying the filtrate with 50% HCl, filtering, washing the precipitate with H2O, and drying gave 11.2 g. Et 2,4-dimethyl-5-pyrrolecarboxylic acid, m. 122°.

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