Day: April 8, 2022

Musil, Zbynek; Zimcik, Petr; Miletin, Miroslav; Kopecky, Kamil; Lenco, Juraj published the article 《Synthesis, separation and UV/Vis spectroscopy of pyrazino-quinoxalinoporphyrazine macrocycles》. Keywords: zinc pyrazino quinoxalino porphyrazine macrocycle complex preparation.They researched the compound: 5,6-Dichloropyrazine-2,3-dicarbonitrile( cas:56413-95-7 ).COA of Formula: C6Cl2N4. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:56413-95-7) here.

Unsym. metal-free and zinc complexes of pyrazino/quinoxalino-porphyrazines (PQP) bearing eight diethylamino groups were synthesized by statistical tetramerization of 2,3-bis(diethylamino)quinoxaline-6,7-dicarbonitrile and 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile in lithium butanolate. For this purpose, a new heteroatom-substituted quinoxaline precursor, 2,3-dichloroquinoxaline-6,7-dicarbonitrile, was prepared and characterized. It is a flexible starting material for new building blocks of quinoxaline-6,7-dicarbonitrile derivatives All the PQPs (including adjacent and opposite isomers) from the statistical mixture were detected and separated by column chromatog. on silica and characterized by MALDI-TOF mass spectrometry, IR, UV/visible and NMR spectroscopy. The effect of the insertion of benzene rings into the tetrapyrazinoporphyrazine (TPP) system is discussed. Each benzene ring insertion into the TPP system causes a bathochromic shift of 22 nm; the dependence is linear. The final tetra[6,7]quinoxalinoporphyrazines were red shifted to 744 and 763 nm for the zinc and metal-free derivative, resp. Splitting of the Q-band was observed for PQPs with lower symmetry.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Hodges, L. Mark; Gonzalez, Javier; Koontz, Jason I.; Myers, William H.; Harman, W. Dean published the article 《β-Electrophilic Additions of Pentaammineosmium(II) η2-Pyrrole Complexes》. Keywords: pyrrole osmium electrophilic addition; alkylation pyrrole osmium complex electrophile; acylation pyrrole osmium complex electrophile; cycloaddition dipolar pyrrole osmium complex; Michael addition dipolar pyrrole osmium complex; ring cleavage azanorbornene osmium complex.They researched the compound: 3-Methyl-1H-pyrrole( cas:616-43-3 ).Recommanded Product: 616-43-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:616-43-3) here.

The reactivity of pyrrole complexes [Os(NH3)5(4,5-η2-L)]2+(OTf)2 (L = pyrrole and alkylated pyrroles, e.g., I, R = H, Me) is surveyed with various electrophiles. The pyrrole ligand undergoes alkylation or acylation with a wide variety of electrophiles (e.g., acids, alkyl triflates, anhydrides, aldehydes, ketones, and Michael acceptors) predominately at the β-position. Depending on reaction conditions, the resulting products are either β-substituted 1H-pyrrole or 3H-pyrrolium complexes, the latter of which resist rearomatization due to the electron-donating properties of the metal. In all cases observed, the initial addition of the electrophile occurs on the ring face anti to Os coordination. The Os(II)-4,5-η2-pyrrole complexes are each in dynamic equilibrium with a minor isomer where the metal binds across C(3) and C(4). In this form, the uncoordinated portion of the pyrrole ring resembles an azomethine ylide, which can undergo a 1,3-dipolar cycloaddition reaction with certain electrophiles. The resulting 7-azanorbornene complexes may be ring-opened with Lewis acids to generate α-substituted 2H-pyrrolium complexes. As with the 3H-pyrrolium species, the 2H-pyrrolium complexes are stabilized by metal coordination and thereby resist rearomatization. The selectivity between Michael addition and dipolar cycloaddition depends on the pyrrole, electrophile, solvent, temperature, the presence of Lewis acids, and in some cases, concentration The iminium C of both 2H- and 3H-pyrrolium tautomers is considerably less electrophilic than its organic analogs, but readily undergoes borohydride reduction to form complexes of 3- and 2-pyrrolines, resp. When pyrrole complexes are combined with alkyne Michael acceptors, the intermediate enolate can be trapped by the iminium C of the 3H-pyrrolium species in DMSO to form a metalated cyclobutene derivative, e.g., II (R1 = COMe, R2 = H; R1 = CO2Me). Decomplexation of most pyrrole and 3-pyrroline derivatives can be accomplished in good yield either by heating or by oxidation of the metal (CeIV or DDQ). Complexes of 2-pyrrolines are considerably more difficult to remove from the metal; however, quaternization or acylation of the nitrogen facilitates their decomplexation.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Shifts in wave number of electronic transitions due to substitution-for furan, pyrrole, and thiophene》. Authors are Santhamma, V..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Synthetic Route of C5H7N. Through the article, more information about this compound (cas:616-43-3) is conveyed.

The transitions, Φ3 → Φ4 and Φ3 → Φ5, were calculated for Me and F substitution on furan, pyrrole, and thiophene. The method used to calculate the shifts is outlined. An effective comparison of the calculated shifts with observed values is not possible due to paucity of exptl. data.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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: 3685-23-2, is researched, SMILESS is N[C@H]1CC[C@H](CC1)C(O)=O, Molecular C7H13NO2Journal, Pharmaceutical Chemistry Journal (Translation of Khimiko-Farmatsevticheskii Zhurnal) called Synthesis and antitumor activity of nonsymmetric phosphoric acid triamides, Author is Kosykhova, L.; Palaima, A.; Stumbryavichyute, Z., the main research direction is phosphoric acid triamide nonsym preparation acute toxicity antitumor activity; amide phosphoric acid nonsym preparation acute toxicity antitumor activity.Reference of cis-4-Aminocyclohexane carboxylic acid.

R1R2P(O)NHR3 (R1, R2 independently = aziridino, N(CH2CH2Cl)2, NMe2, morpholino or NHCH2CH2OH; R3 = 4-R-substituted cyclohexyl (R = H, cis- and trans-CO2H, cis- and trans-CO2Et)) were prepared and tested for acute toxicity and antitumor activity. All the 12 tested compounds possess a lower antitumor activity as compared to that of the reference drug thiophosphamide. The antitumor activity of nonsym. phosphoric acid triamides is determined for the most part by the nature of amide residues attached at the P atom. The antitumor effect can be varied within a broad range by changing this residue, the maximum antitumor activity being inherent in nonsym. triamides containing the ethylenimine residue.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Pyrrole Syntheses from Amino Ketones with Ketones and Ketone Esters》. Authors are Piloty, O.; Hirsch, P..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Computed Properties of C5H7N. Through the article, more information about this compound (cas:616-43-3) is conveyed.

The following pyrrole derivatives have been prepared by treating aqueous solutions of the HCl salts of amino ketones containing an excess of alk. with a ketone or ketone ester and allowing to stand a long time at a slightly elevated temperature in closed vessels. α-β’-Dimethylpyrrole, from Ac2NH2.HCl and AcMe; yield, 30%. α-Phenyl-β’-methylpyrrole, from 10 g. AcCH2NH2.HCl and 5 g. AcPh, m. 152°; yield, 1 g. α,β,β’-Trimethylpyrrole, from AcEt; yield, 28%. α-Ethyl-β,β’-dimethylpyrrole, b10 77-8° (yield, 0.4 g. from 14 g. AcCH3NH2.HCl and 10 g. Et2CO); picrjate, bright yellow, striated prisms, m. 122.5°. α,β,α’-Trimethylpyrrole, from AcCHMeNH2 and AcMe; yield, 50%. Some tetramethylpyrazine is formed in this reaction. AcCHMeNH2 and AcEt react only slowly and incompletely; the chief product is the pyrazine, but a little α,β,α’,β’-tetramethylpyrrole picrate (cf. Fischer and Bartholomäus, C. A., 7, 780) was isolated. Et α,β’-dimethylpyrrole-β-carboxylate, from AcCH2NH2 and AcCH2CO2Et. Monoethyl β-methylpyrrole-α’,β’-dicarboxylate, from 19 g. HO2CCOCH2CO2Et and 11 g. AcCH2NH2.HCl, monoclinic prisms, m. 196° (yield, 2-3 g.), converted by 20 hrs. b. with excess of 20% KOH into β-methylpyrrole-β’ (or α’)-carboxylic acid, flocks, m. 149°, losing CO2 and forming β-methylpyrrole, b11 45°. Monoethyl α,β-dimethylpyrrole-α’,β’-dicarboxylate, from AcCHMeNH2 and HO2CCOCH2CO2Et, prisms, m. 201° (loss of CO2). α,β-Dimethylpyrrole-β’ (or α’)-carboxylic acid, m. 188°. α,β-Dimethylpyrrole, b11 62°; picrate, bright yellow, felted needles, m. 146-5°; contrary to all other pyrrole derivatives, it has the comp. C18H21O7N5, i. e., 2 mols. pyrrole: 1 mol. picric acid.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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.Lee, Bum Hoon; Jaung, Jae Yun; Jeong, Sung Hoon researched the compound: 5,6-Dichloropyrazine-2,3-dicarbonitrile( cas:56413-95-7 ).Category: chiral-oxygen-ligands.They published the article 《Synthesis and dyeing properties of dicyanopyrazine dyes》 about this compound( cas:56413-95-7 ) in Journal of the Korean Fiber Society. Keywords: cyanopyrazine dye preparation use polyamide polyester. We’ll tell you more about this compound (cas:56413-95-7).

Reaction of 2,3-dichloro-5,6-dicyanopyrazine with various Fischer’s base type enamines gave the corresponding 2-chloro-5,6-dicyanopyrazine derivatives The reactive-disperse dyes showed large differences in λmax from solution to solid state resulting from strong intermol. π-π interactions. These dyes have rather small mol. size but have a strong intramol. charge-transfer chromophoric system. The absorption maxima of these compounds were observed at 463∼560 nm. The electronic character of the substituents in the dyes strongly affects their absorption spectra, producing bathochromic shifts depending on both the basicity of the heterocyclic moiety and the enlargement of the π-conjugated system. The dyeability of 2 of the dyes toward polyester and nylon fiber were generally good. Wash, perspiration, and rubbing fastness were excellent, while light fastness was poor, probably due to the oxidation of the enamine moiety.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereochemical investigations of 1,4-substituted cyclohexane derivatives. 4-Hydroxy- and 4-aminocyclohexane-1-carboxylic acid and their esters; and 4-hydroxy-1-hydroxymethylcyclohexane》. Authors are Schneider, Woldemar; Huettermann, A..The article about the compound:cis-4-Aminocyclohexane carboxylic acidcas:3685-23-2,SMILESS:N[C@H]1CC[C@H](CC1)C(O)=O).Electric Literature of C7H13NO2. Through the article, more information about this compound (cas:3685-23-2) is conveyed.

Malonic ester synthesis with ethyl β-chloropropionate, followed by ring closure of the product obtained gave 4-hydroxy-1-cyclohexanone (I). Hydrogenation of I (Raney-Ni, atm. pressure, room temperature) in alk. medium gave cis-4-hydroxycyclohexane-1-carboxylic acid (cis-II), m. 152°; Et ester, (cis-III) b12 130°. Hydrogenation of ethyl 4-hydroxybenzoic acid (Raney-Ni, 150 atm., 150°) gave trans-III, b13 139-140°, saponification of which gave the trans-II, m. 119.5°. Reduction of trans-III with Na-EtOH or LiAlH4, gave a cis-trans mixture of 4-hydroxy-1-hydroxymethylcyclohexane (IV), from which the trans isomer (V) was separated, m. 104°; the cis isomer (VI) was recovered by distillation from the residue. Hydrogenation of ethyl 4-aminobenzoic acid (Ru-C, 110 atm., 80°) gave a cis-trans mixture of 4-amino-1-carbethoxycyclohexane (VII), which was separated by distillation, giving cis-VII and trans-VII. The exptl. determined dipole moments (μ in Debye units) of these compounds are: cis-II 2.10 ± 0.1, trans-II 246 ± 0.002, cis-III 2.86 ± 0.03, trans-III 2.56 ± 0.04, VI 2.29 ± 0.02, V 2.60 ± 0.1, cis-VII 2.60 ± 0.01, and trans-VII 2.44 ± 0.02.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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: 3-Methyl-1H-pyrrole, is researched, Molecular C5H7N, CAS is 616-43-3, about TD-GC-MS investigation of the VOCs released from blood plasma of dogs with cancer.Quality Control of 3-Methyl-1H-pyrrole.

An anal. TD-GC-MS method was developed and used for the assessment of volatile organic compounds (VOCs) released from the blood plasma of dogs with/without cancer. VOCs released from 40 samples of diseased blood and 10 control samples were compared in order to examine the difference between both sample groups that were showing qual. similar results independent from the disease’s presence. However, mild disturbances in the spectra of dogs with cancer in comparison with the control group were observed, and six peaks (tentatively identified by comparison with mass spectral library as hexanal, octanal, toluene, 2-butanone, 1-octen-3-ol and pyrrole) revealed statistically significant differences between both sample groups, thereby suggesting that these compounds are potential biomarkers that can be used for cancer diagnosis based on the blood plasma TD-GC-MS anal. Statistical comparison with the application of principal component anal. (PCA) provided accurate discrimination between the cancer and control groups, thus demonstrating stronger biochem. perturbations in blood plasma when cancer is present.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A suitable solvent for molecular-weight determinations according to Rast》. Authors are Wendt, Gerhard.The article about the compound:cis-4-Aminocyclohexane carboxylic acidcas:3685-23-2,SMILESS:N[C@H]1CC[C@H](CC1)C(O)=O).Recommanded Product: 3685-23-2. Through the article, more information about this compound (cas:3685-23-2) is conveyed.

The lactam (I) of cis-hexahydro-p-aminobenzoic acid (II), m. 196°, results in 3.3-g. yield from 5 g. of the mixture of cis- and trans-II. For the separation of the 2 isomers of II, the hydrogenation product from 4 g. of p-H2NC6H4CO2H in 20 cc. H2O is treated with 180 cc. absolute EtOH to precipitate 1.9 g. crude cis-II, 2 crystallizations of which from dilute EtOH give the pure acid, m. 304-5°, sublimes 210-20°/6 × 10-4 mm.; contrary to the observation of Orthner and Hein (C. A. 27, 4776) the acid melts before sublimation; their transformation of the cis to the trans acid could not be verified. Addition of 400 cc. ether to the filtrate from the cis acid gives (standing 24 hrs.) 1.9 g. crude trans acid; this is purified by solution in 10 cc. H2O and precipitation with 125 cc. absolute EtOH; it m. 186-8° (decomposition), sublimes 210-20°/3 × 10-4 mm. I is a suitable substitute for camphor in the mol.-weight determination according to Rast. The m.-p. lowering constant is 40 (the same as camphor); the molar heat of melting is 1.37 kg.-cal. (for camphor 1.55 kg.-cal.). Because of the solubility in I, it is specially suitable for the determination of the mol. weights of di- and tripeptides (e. g., Me p-aminobenzoyl-p-aminobenzoate, Me p-nitrobenzoyl-p-aminobenzoyl-p-aminobenzoate, leucylglycine, glycylleucine), disaccharides (e. g., saccharose and cellobiose) and nucleosides (e. g., uridine and adenosine), most of which are insoluble in camphor. However, certain compounds (uric acid, creatine, glycylglycine) are insoluble in I.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Product Details of 616-43-3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3-Methyl-1H-pyrrole, is researched, Molecular C5H7N, CAS is 616-43-3, about Improved preparation of 3-methylpyrrole. Laboratory note. Author is Elguero, Jose; Jacquier, Robert; Shimizu, Bernard.

An improved synthesis of 3-methylpyrrole (I) and the N.M.R. spectra of the intermediates and product are given. Thus, 20 g. 3-carbethoxy-4-methyl-2-pyrrolecarboxylic acid is refluxed 1 hr. with 300 ml. 40% KOH, cooled, acidified with dilute HCl, filtered, washed with water, and dried to give 70% 4-methylpyrrole-2,3-dicarboxylic acid (II), m. 225°. II (12 g.) is added to 1 g. powd. Cu and heated under 50 mm. to dist. 87% I.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate