Tag: M.W=100-200

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: 1195-58-0, is researched, SMILESS is N#CC1=CC(C#N)=CN=C1, Molecular C7H3N3Journal, Journal of Heterocyclic Chemistry called Correlation of 2-, 3-, 4- and disubstituted pyridine gas-phase proton affinities with ab initio calculated energies at the STO-3G basis set level, Author is Caronna, Tullio; Vittimberga, Bruno M., the main research direction is proton affinity pyridine derivative energy calculation; ab initio protonation pyridine energy.Recommanded Product: Pyridine-3,5-dicarbonitrile.

Total energies of 2-, 3-, 4- and disubstituted pyridines were calculated for the salt and the free base using ab initio MO calculations at the STO-3G basis set level. In each set, the difference in energy, ΔEH, between the salt and the free base was calculated and plotted against exptl. derived gas-phase proton affinities. The correlation was very good for each of the substituent categories listed. All of the energies and proton affinities were then plotted together on the same graph. The result was an excellent correlation with r = 0.97. The linear equation for gas phase proton affinity, PAB = 28.51 + 435.45ΔEH kcal/mol, was derived from this plot and was used to calculate proton affinities for all 31 compounds used in this study as well as for a series of dicyanopyridines for which values of proton affinity are not available at this time.

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Name: 1-(4-Chlorophenyl)pyrrolidin-2-one. 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: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Late-stage oxidative C(sp3)-H methylation. Author is Feng, Kaibo; Quevedo, Raundi E.; Kohrt, Jeffrey T.; Oderinde, Martins S.; Reilly, Usa; White, M. Christina.

Frequently referred to as the ‘magic Me effect’, the installation of Me groups-especially adjacent (α) to heteroatoms-has been shown to dramatically increase the potency of biol. active mols.1-3. However, existing methylation methods show limited scope and have not been demonstrated in complex settings1. Here, we report a regioselective and chemoselective oxidative C(sp3)-H methylation method that is compatible with late-stage functionalization of drug scaffolds and natural products. This combines a highly site-selective and chemoselective C-H hydroxylation with a mild, functional-group-tolerant methylation. Using a small-mol. manganese catalyst, Mn(CF3PDP), at low loading (at a substrate/catalyst ratio of 200) affords targeted C-H hydroxylation on heterocyclic cores, while preserving electron-neutral and electron-rich aryls. Fluorine- or Lewis-acid-assisted formation of reactive iminium or oxonium intermediates enables the use of a mildly nucleophilic organoaluminum methylating reagent that preserves other electrophilic functionalities on the substrate. We show this late-stage C(sp3)-H methylation on 41 substrates housing 16 different medicinally important cores that include electron-rich aryls, heterocycles, carbonyls and amines. Eighteen pharmacol. relevant mols. with competing sites, including drugs (for example, tedizolid) and natural products, are methylated site-selectively at the most electron rich, least sterically hindered position. We demonstrate the syntheses of two magic Me substrates, an inverse agonist for the nuclear receptor RORc and an antagonist of the sphingosine-1-phosphate receptor-1, via late-stage methylation from the drug or its advanced precursor. We also show a remote methylation of the B-ring carbocycle of an abiraterone analog. The ability to methylate such complex mols. at late stages will reduce synthetic effort and thereby expedite broader exploration of the magic Me effect in pursuit of new small-mol. therapeutics and chem. probes.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《On cyclic intermediates in substitution reactions. VII. The alkaline solvolysis of some N-aryl-4-bromobutanamides》. Authors are Heine, Harold W.; Love, Peter; Bove, John L..The article about the compound:1-(4-Chlorophenyl)pyrrolidin-2-onecas:7661-33-8,SMILESS:O=C1N(C2=CC=C(Cl)C=C2)CCC1).Category: alcohols-buliding-blocks. Through the article, more information about this compound (cas:7661-33-8) is conveyed.

cf. C.A. 49, 1556b. The rates of the solvolysis of 3 N-aryl-4-bromobutanamides have been studied in MeOH. The rates of the reaction as determined by the measurement of the release of bromide ion are 1st order with respect to MeO-. The reaction products are the corresponding pyrrolidones. These results are discussed in terms of a mechanism involving the formation and conversion of a bromoamido ion to a pyrrolidone. SOCl2 (20 cc.) added dropwise to 37.1 g. Br(CH2)3CO2H, the mixture held 2 days at room temperature, the excess SOCl2 removed in vacuo, and the residue distilled gave a distillate, b31 88-90°, nD201.4899; a 37.1-g. sample of the distillate added dropwise with stirring to 37.2 g. PhNH2 in 500 cc. CHCl3, the mixture stirred 15 min., the precipitate filtered and washed with CHCl3, the combined filtrate and washing concentrated in vacuo, and the crude residue dissolved in ligroine, b. 65-110°, cooled, and then chilled to -78° gave 38% Br(CH2)3CONHPH (I), m. 75-6°. In the same manner except with a reaction time of 4 hrs. was prepared the p-Me derivative (II) of I, m. 90-1° (from petr. ether), in 63.2% yield. The p-Cl derivative (III) of I, m. 100-1° (from petr. ether), was prepared with a reaction time of 2 hrs. in 69.2% yield. A solution (100 cc.) 0.05M in NaOMe and 0.05M in III kept at 22.9° until all bromide ion had been released, the MeOH evaporated in vacuo, the residue washed with H2O, and the residue dried at 50° and recrystallized from petr. ether (b. 30-60°) gave 0.940 g. 1-(p-chlorophenyl)pyrrolidone (IV), m. 95-7°. The average rate constants of the alk. solvolyses determined at 22.90° were: III 5.65, I 1.80, and II 1.03 × 10 l./min./mole.

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Safety of 1-(4-Chlorophenyl)pyrrolidin-2-one. 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: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Selective cleavage and reconstruction of C-N/C-C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines. Author is He, Yan; Yang, Jintao; Zhang, Xinying; Fan, Xuesen.

Selective cleavage and functionalization of C-N/C-C bonds in saturated cyclic amines under the promotion of oxoammonium salt and tert-Bu hydroperoxide in the presence of different additives was developed. To be specific, cascade cleavage and reconstruction of C-N and C-C bonds took place under acidic conditions to provide pyrrolidin-2-ones. Under basic conditions, on the other hand, selective cleavage and functionalization of C-C bonds occurred to afford multi-functionalized acyclic N-formal amines. In addition, studies for revealing the intriguing reaction mechanisms was also been performed.

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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: 1195-58-0, is researched, SMILESS is N#CC1=CC(C#N)=CN=C1, Molecular C7H3N3Journal, Article, ACS Omega called Thermodynamic Parameters of Elementary Steps for 3,5-Disubstituted 1,4-Dihydropyridines To Release Hydride Anions in Acetonitrile, Author is Zhao, Hui; Li, Yang; Zhu, Xiao-Qing, the main research direction is dihydropyridine hydride ion source thermodn.Computed Properties of C7H3N3.

A series of 3,5-disubstituted 1,4-dihydropyridine derivatives including the derivative with two chiral centers, 6H (R2 = CH3, CH2Ph), as a new type of organic hydride source were synthesized and characterized. The thermodn. driving forces (defined as enthalpy changes or standard redox potentials) of the 6 elementary steps for the organic hydrides to release hydride ions in acetonitrile were measured by isothermal titration calorimeter and electrochem. methods. The impacts of the substituents and functional groups bearing the N1 and C3/C5 positions on the thermodn. driving forces of the 6 elementary steps were examined and analyzed. Moreover, the results showed that the reaction mechanism between the chiral organic hydride and activated ketone (Et benzoylformate) was identified as the concerted hydride transfer pathway based on the thermodn. anal. platform. These valuable and crucial thermodn. parameters will provide a broadly beneficial impact on the applications of 3,5-disubstituted 1,4-dihydropyridine derivatives in organic synthesis and pharmaceutical chem.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction of Grignard reagent with 3,5-dicyanopyridines》. Authors are Lukes, R.; Kuthan, J..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Application of 1195-58-0. Through the article, more information about this compound (cas:1195-58-0) is conveyed.

Et2O solutions of 3,5-dicyanopyridines reacted at 20-40° with MeMgI (Ia) or EtMgBr (Ib) in 4-6-fold excess to form NH.CR1:C(CN).CR2:C(CN).CHR3 or NH.CR1:C(CN).CHR2.C(CN):CR3. The following were prepared: R1 = R2 = R3 = H (I); R1 = R2 = H, R3 = Me (II); R1 = R3 = H, R2 = Et (III); R1 = Me, R2 = R3 = H (IV); R1 = R3 = Me, R3 = H (V); R1 = R3 = Me, R2 = H (VI); R1 = H, R2 = R3 = Me (VII); R1 = H, R2 = Me, R3 = Et (VIII); R1 = H, R2 = Et, R3 = Me (IX); R1 = R3 = Me, R2 = H (X); R1 = R2 = R3 = Me (XI); R1 = R2 = H, R3 = Me (XII); R1 = R3 = H, R2 = Et (XIII); R1 = R2 = Me, R3 = H (XIV); R1 = R2 = R3 = Me (XV). I with Ia gave 76% XII, I with Ib 65% XIII, II with Ia 66% VII, II with Ib 48% VIII, III with Ia 89% IX, IV with Ia about 43% X and XIV, V with Ia 82% XI, VI with Ia 35% XV.

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Volke, J.; Skala, V. published an article about the compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1 ).Category: alcohols-buliding-blocks. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1195-58-0) through the article.

Electrochem. reduction of mono- and dicyanopyridines at a Hg electrode proceded via intermediates containing a cyclic π-electron septet formed after uptake of the 1st electron; these intermediates underwent either protonation, dimerization, or further 1-electron reduction, depending on the position of the cyano group(s), the acidity of the medium, and the electrode potential. This mechanism was substantiated by LCAO-MO and SCF calculations; the exptl. half-wave potentials were correlated to the energy of the lowest free MO of the substrate.

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Safety of Pyridine-3,5-dicarbonitrile. 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: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Dihydropyridines. XVII. π-Electronic structure and reactivity of alkyl 3,5-dicyanopyridines.

The π-electronic structure of alkyl 3,5-dicyanopyridines was studied by the Hueckel M.O. L.C.A.O. method. The heteroatom model was used in the calculations The exptl. course of nucleophilic reactions was in agreement with the calculated superdelocalizabilities. Some of the exptl. excitation energies depended linearly on the calculated transition energies. Correlation was found between the values of proton shifts in the N.M.R. spectra of dicyanopyridines and the corresponding electron densities.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides, the main research direction is aryl oxazolidinone preparation arylamide copper catalyst; oxazolidinone amide heteroaryl iodide arylation.HPLC of Formula: 7661-33-8.

N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature Excellent chemoselectivity reached between aryl iodides and aryl bromides, and a wide range of functional groups tolerated the reaction conditions, which led to the formation of greatly diverse N-arylation products.

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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.Donnier-Marechal, Marion; Carato, Pascal; Larchanche, Paul-Emmanuel; Ravez, Severine; Boulahjar, Rajaa; Barczyk, Amelie; Oxombre, Benedicte; Vermersch, Patrick; Melnyk, Patricia researched the compound: 1-(4-Chlorophenyl)pyrrolidin-2-one( cas:7661-33-8 ).Synthetic Route of C10H10ClNO.They published the article 《Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands》 about this compound( cas:7661-33-8 ) in European Journal of Medicinal Chemistry. Keywords: aminoalkyl benzamide preparation sigma protein cytotoxicity human docking SAR; benzyl methyl propanamine preparation sigma protein safety human SAR; Benzamide; CNS; Sigma protein. We’ll tell you more about this compound (cas:7661-33-8).

A series of novel N-(aminoalkyl)benzamide derivatives such as I [m = 2, 3; R1 = Me; R2 = Bn, (CH2)2C6H4; R1R2 = (CH2)4, (CH2)2O(CH2)2, (CH2)2NMe(CH2)2, etc.; R3 = H, 4-n-Bu, 4-Cl, etc.] and N-benzyl-N-methyl-propan-1-amine derivatives II [X = CH2NH, SO2NH, NHC(O)] was designed, synthesized and pharmacol. evaluated. In vitro competition binding assays against sigma proteins (sigma-1 S1R and sigma-2 S2R) revealed that most of them conferred S2R/S1R selectivity toward without cytotoxic effects on SY5Y cells, especially with compounds I [m = 2, 3; R1 = Me; R2 = Bn]. Some selected compounds were also evaluated for their agonist and antagonist activities on a panel of 40 receptors and results showed the importance of the nature and the position with halogeno atom on the benzamide scaffold, the length chain and also the contribution of the hydrophobic part on the amine group. Among them, compounds I [m = 2, 3; R1 = Me; R2 = Bn; R3 = 4-Cl, 4-CN, 4-NO2] showed excellent affinity for S1R (Ki = 1.2-3.6 nM), selectivity for S2R (Ki up to 1400 nM) and high selectivity index (IC50(SY5Y)/Ki(S1R) ratio from 28/000 to 83/000). Furthermore, these compounds I and II presented an excellent safety profile over 40 other receptors.

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