Category: chiral-nitrogen-ligands

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: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Synthesis, spectral and structural studies on NiS2PN and NiS2P2 chromophores and use of Ni(II) dithiocarbamate to synthesize nickel sulfide and nickel oxide for photodegradation of dyes.Application In Synthesis of 1,2-Bis(diphenylphosphino)ethane.

The substitution of one of the dithiocarbamate ligands in homoleptic [Ni(dtc)2] (1) complex (dtc = N,N-di(4-methoxybenzyl)dithiocarbamate) with phosphine ligands gave heteroleptic [Ni(dtc)(PPh3)(NCS)] (2), [Ni(dtc)(PPh3)2] ClO4 (3) and [(dtc)(dppe)] ClO4 (4) complexes. The complexes 2-4 were characterized by elemental anal., spectroscopy and single crystal x-ray diffraction anal. Single crystal x-ray diffraction studies revealed that 2-4 adopt distorted square planar geometry. Noncovalent interactions in 2-4 were quantified using Hirshfeld surface anal. The study of single crystal x-ray diffraction of 2-4 shows that various interactions such as C-H···π (chelate), C-H···π, C-H···O and C-H···S among mols. of complexes 2-4, participate in cooperative way to stabilize the supramol. interactions. DFT calculations were used to determine the electronic structure and properties of 2. The HOMO-LUMO energy difference (2.7445 eV) is small which shows the low kinetic stability of 2. Nanoparticles of Ni sulfide and Ni oxide were successfully synthesized by solvothermal and thermal decomposition of 1, resp. and characterized by powder x-ray diffraction (PXRD), High Resolution SEM (HRSEM), Energy Dispersive Spectroscopy (EDS) and UV Diffuse Reflectance Spectroscopy (UV-DRS). The photocatalytic activity of both nanoparticles was studied for degradation of methylene blue and rhodamine 6G under UV irradiation The Ni oxide has higher photocatalytic activity than Ni sulfide.

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Reference of 1,5-Dibromopentane. 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: 1,5-Dibromopentane, is researched, Molecular C5H10Br2, CAS is 111-24-0, about Design, synthesis and biological evaluation of rasagiline-clorgyline hybrids as novel dual inhibitors of monoamine oxidase-B and amyloid-β aggregation against Alzheimer’s disease. Author is Xie, Sai-Sai; Liu, Jing; Tang, Chunli; Pang, Chengyun; Li, Qing; Qin, Yuelian; Nong, Xiaojie; Zhang, Zhipeng; Guo, Jie; Cheng, Maojun; Tang, Weizhong; Liang, Ningsheng; Jiang, Neng.

A series of rasagiline-clorgyline hybrids was designed, synthesized and investigated in vitro for their inhibition of monoamine oxidase and amyloid-β aggregation. Most of compounds were found to be selective and highly potent hMAO-B inhibitors showing IC50 values in the nanomolar, and exhibited a moderate inhibition of amyloid-β aggregation. 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one (6j) was the most interesting compound identified in this research, endowed with higher hMAO-B potency (IC50 = 4 nM) and selectivity (SI > 25000) compared to the reference selective inhibitor rasagiline (IC50 = 141 nM, SI > 355), and exhibited good inhibitory activity against Aβ1-42 aggregation (40.78%, 25μM). Kinetic and mol. modeling studies revealed that 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one was a competitive reversible inhibitor for hMAO-B. Moreover, compound 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one displayed low toxicity and good neuroprotective effects in SH-SY5Y cell assay, and could penetrate the blood-brain barrier according to the parallel artificial membrane permeability assay. Pharmacokinetics assay revealed that 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one possessed good pharmacokinetic profiles after i.v. and oral administrations. Overall, these results highlighted that 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one was an effective and promising multitarget agent against Alzheimer’s disease.

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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.Chermahini, Alireza Najafi; Teimouri, Abbas; Momenbeik, Fariborz; Zarei, Amin; Dalirnasab, Zeinab; Ghaedi, Aseyeh; Roosta, Mostafa researched the compound: 5-(4-Pyridyl)-1H-tetrazole( cas:14389-12-9 ).COA of Formula: C6H5N5.They published the article 《Clay-catalyzed synthesis of 5-substituent 1-H-tetrazoles》 about this compound( cas:14389-12-9 ) in Journal of Heterocyclic Chemistry. Keywords: aryl substituted tetrazole preparation; arylnitrile sodium azide cycloaddition clay. We’ll tell you more about this compound (cas:14389-12-9).

In this study, the possibility of 5-substituted 1-H-tetrazoles synthesis using clays as catalyst was investigated. The reaction of a series of aromatic nitriles with sodium azide was catalyzed by montmorillonite K-10 or kaolin clays in water or DMF as solvent. Conventional heating or ultrasonic irradiation was used to promote reaction. The amount of nitrile to sodium azide mole ratio, amount of catalyst, reaction time, and solvent type were optimized. The versatility of this method was checked by using various nitriles, which showed reasonable yields of tetrazole formation. It was found that using nitriles with electron-withdrawing groups result in both higher yields and lower reaction times. The catalysts could be reused several times without significant loss of their catalytic activity. Compared to conventional heating, ultrasonic irradiation reduced reaction times and increased catalyst activity. The present procedure is green and offers advantages, such as shorter reaction time, simple workup, and recovery and reusability of catalyst. J. Heterocyclic Chem., (2010).

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of triarylphosphines and triarylphosphine oxides through the use of organolithium compounds》. Authors are Mikhailov, B. M.; Kucherova, N. F..The article about the compound:Tri(naphthalen-1-yl)phosphinecas:3411-48-1,SMILESS:C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2).SDS of cas: 3411-48-1. Through the article, more information about this compound (cas:3411-48-1) is conveyed.

All operations with RLi were run in a N atm. To a solution of PhLi (from 5 g. PhBr, 0.44 g. Li, and 30 ml. absolute Et2O) was added with cooling over 15-20 min. 1.3 g. PCl3 in 20 ml. Et2O, the mixture was decompose with H2O after subsidence of reaction, and the organic layer washed with 10% NaOH to give 1.9 g. (61.3%) Ph3P, m. 77-8° (from EtOH). Similarly ArLi from 4 g. 1-C10H7Br, 0.27 g. Li, and 55 ml. Et2O, treated with 0.9 g. PCl3 in 50 ml. Et2O, water added, the mixture made alk. with NaOH, and the organic layer evaporated, gave 26.9% (1-C10H7)3P, m. 276-8°; crystallized from CHCl3 it forms a CHCl3 adduct, m. 260-2°, losing the solvent at 110°; the pure product m. 278-80°. 9-Bromophenanthrene, (5 g.) added to a BuLi solution from 3 g. BuCl, 0.5 g. Li, and 30 ml. Et2O, precipitated the Li derivative; the solution decanted and the washed precipitate suspended in fresh Et2O and treated with 0.9 g. PCl3 in Et2O, gave a red color which vanished as the addition continued; the usual treatment gave 72% tri-9-phenanthrylphosphine, m. 374-6° (from MePh). Similarly, 9-bromoanthracene gave 20% tri-9-anthrylphosphine, m. 270-3° (from C6H6), and some 18% anthracene. To 0.017 mole PhLi in 32 ml. Et2O was added 5 g. 9,10-dibromoanthracene and, after 20 min., 0.67 g. PCl3 in 15 ml. Et2O, yielding a red solution and precipitate; after 10 min. the usual treatment gave 3.1 g. crude product, which, extracted with hot MePh, gave 1.2 g. tris(9-bromo-10-anthryl)phosphine, orange-yellow, m. 206-8°. To BuLi from 1.1 g. BuCl, 0.2 g. Li, and 20 ml. Et2O was added 2 g. 7-bromobenz[a]anthracene, then 0.35 g. PCl3 in Et2O; the usual treatment gave 53% tris(1,2-benz[a]anthracen-7-yl)phosphine, m. 192-4° (after treatment with hot C6H6). PhLi solution with POCl3 gave 65% Ph3PO, m. 155-7° (from Et2O); 1-C10H7Li gave after 0.5 hr., 38.5% tri-1-naphthylphosphine oxide, m. 335-6.5° (from much CHCl3); 9-phenanthryllithium gave after 10 min. 49% tri-9-phenanthrylphosphine oxide, m. 354-6° (from MePh); while 10-bromo-1,2-benzanthracene yielded tris(benz[a]-anthracen-7-yl)phosphine oxide, m. 191-3° (from C6H6-Et2O). The reaction with POCl3 is vigorous and is best run with ice cooling.

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Application of 1663-45-2. 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: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Heterobimetallic μ2-carbido complexes of platinum and tungsten. Author is Burt, Liam K.; Hill, Anthony F..

The W-Pt μ-carbido complex [WPt(μ-C)Br(CO)2(PPh3)2(Tp*)] (Tp* = hydrotris(dimethylpyrazol-1-yl)borate) undergoes facile substitution of both bromide and phosphine ligands to afford a diverse library of μ-carbido complexes that includes [WPt(μ-C)Br(CO)2(dppe)(Tp*)], [WPt(μ-C)(NCMe)(CO)2(PPh3)2(Tp*)]OTf, [WPt(μ-C)(S2CNEt2)(CO)2(PPh3)(Tp*)], [WPt(μ-C)(bipy)(CO)2(PPh3)(Tp*)]PF6, [WPt(μ-C)(phen)(CO)2(PPh3)(Tp*)]PF6, [WPt(μ-C)(terpy)(CO)2(Tp*)]PF6, [WPt(μ-C)(CO)2(PPh3)(Bp*)(Tp*)], [WPt(μ-C)(CO)2(PPh3)(Tp*)2] and [WPt(μ-C)(bipy)(CO)2(PPh3)(Bm)(Tp*)], most of which were structurally characterized.

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Recommanded Product: 5-(4-Pyridyl)-1H-tetrazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about A Dual-Functional Luminescent MOF Sensor for Phenylmethanol Molecule and Tb3+ Cation. Author is Yi, Fei-Yan; Gu, Minli; Wang, Shi-Cheng; Zheng, Jia-Qi; Pan, Luqing; Han, Lei.

A highly luminescent porous metal-organic framework Cd3(L)2.5(4-PTZ)(DMF)3, labeled as NBU-9, has been designedly synthesized based on Cd(NO3)2·4H2O and mixed ligands of 4-(1H-tetrazol-5-yl)pyridine (4-HPTZ) with N-coordinated sites and thiophene-2,5-dicarboxylic acid (H2L) with heteroat. (S) ring and carboxylate groups in N,N-dimethylformamide (DMF) at 100 °C for 3 days. The interesting result is that this compound NBU-9 can be also obtained via the mixed raw materials of Cd(NO3)2·4H2O, 4-cyanopyridine, NaN3, and H2L under solvothermal condition at a higher temperature of 140 °C for 3 days, involving in situ ligand synthesis of 4-HPTZ. Its structure was identified by single-crystal X-ray study, powder X-ray diffraction, element anal., and TGA results. Structural anal. shows that the three-dimensional framework of NBU-9 contains cubic channels of 9.59 × 10.26 Å2 covered by a large number of open S- and O-coordinated sites and can be simplified into a 8-connected uninodal eca net with high potential solvent accessible volumes of 34.1%. Its luminescent properties demonstrate that NBU-9 as a multifunctional sensory material realizes the selective detection for the phenylmethanol mol. on the basis of fluorescence quenching mechanism and effectively sensitizing the visible emitting of the Tb3+ cation based on luminescence enhancement.

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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Tang, Cen; Ku, Kang Hee; Lennon Luo, Shao-Xiong; Concellon, Alberto; Wu, You-Chi Mason; Lu, Ru-Qiang; Swager, Timothy M. published an article about the compound: 1,2-Bis(diphenylphosphino)ethane( cas:1663-45-2,SMILESS:P(CCP(C1=CC=CC=C1)C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4 ).COA of Formula: C26H24P2. 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:1663-45-2) through the article.

The capping reagent plays an essential role in the functional properties of gold nanoparticles (AuNPs). Multiple stimuli-responsive materials are generated via diverse surface modification. The ability of the organic ligand shell on a gold surface to create a porous shell capable of binding small mols. is demonstrated as an approach to detect mols., such as methane, that would be otherwise difficult to sense. Thiols are the most studied capping ligands of AuNPs used in chemiresistors. Phosphine capping groups are usually seen as stabilizers in synthesis and catalysis. However, by virtue of the pyramidal shape of triarylphosphines, they are natural candidates to create intrinsic voids within the ligand shell of AuNPs. In this work, surface-functionalized (capped) AuNPs with chelating phosphine ligands are synthesized via two synthetic routes, enabling chemiresistive methane gas detection at sub-100 ppm levels. These AuNPs are compared to thiol-capped AuNPs, and studies were undertaken to evaluate structure-property relationships for their performance in the detection of hydrocarbons. Polymer overcoatings applied to the conductive networks of the functionalized AuNP arrays were shown to reduce resistivity by promoting the formation of conduction pathways with decreased core-core distance between nanoparticles. Observations made in the context of developing methane sensors provide insight relevant to applications of phosphine or phosphine-containing surface groups in functional AuNP materials.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Application of 3411-48-1. 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: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about Pd-catalyzed addition of boronic acids to vinylogous imines: a convenient approach to 3-sec-alkyl substituted indoles.

A convenient approach to 3-sec-alkyl substituted indoles was developed via palladium-catalyzed addition of arylboronic acids to vinylogous imines generated in situ from sulfonylindoles under mild conditions. E.g, in presence of Pd(OAc)2/tri-1-naphthylphosphine/K2CO3, reaction of sulfonylindole (I) with PhB(OH)2 gave 90% 3-sec-alkyl substituted indole (II).

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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, ChemPlusChem called Two Six-Connected MOFs with Distinct Architecture: Synthesis, Structure, Adsorption, and Magnetic Properties, Author is Ren, Guo-Jian; Han, Song-De; Liu, Yan-Qing; Hu, Tong-Liang; Bu, Xian-He, which mentions a compound: 14389-12-9, SMILESS is C1(C2=NN=NN2)=CC=NC=C1, Molecular C6H5N5, Computed Properties of C6H5N5.

By assembling CoII ions and a combination of 5-(4-pyridyl)tetrazole (4-ptz) and formate ions, two distinct metal-organic frameworks, [Co3(4-ptz)5(HCOO)(H2O)2] and [Co3(4-ptz)4(DMF)2(HCOO)2] (DMF=N,N’-dimethylformamide), were synthesized. They were both characterized by single-crystal x-ray diffraction, IR spectroscopy, TGA, and powder X-ray diffraction. Structural analyses revealed that by slightly modulating the coordination environment of the trinuclear cobalt cluster, two complexes were formed featuring unusual six-connected nets reminiscent of a pyrazole-type linear trinuclear cobalt cluster as compared with the classic eight-connected bcu topol. In addition, [Co3(4-ptz)5(HCOO)(H2O)2] interacted strongly with CO2, with an adsorption enthalpy of 29.2 kJ mol-1, and in a selectivity study, the uptake ratios of CO2/N2 (from a 15:85 mixture) and CO2/CH4 (50:50 mixture) were 77.6 and 37.7, resp. Magnetic studies on both complexes revealed weak antiferromagnetic coupling between the CoII ions.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Tetrazole analogs of pyridinecarboxylic acids》. Authors are McManus, J. M.; Herbst, Robert M..The article about the compound:5-(4-Pyridyl)-1H-tetrazolecas:14389-12-9,SMILESS:C1(C2=NN=NN2)=CC=NC=C1).Name: 5-(4-Pyridyl)-1H-tetrazole. Through the article, more information about this compound (cas:14389-12-9) is conveyed.

The isomeric 5-tetrazolylpyridines were prepared as analogs of the pyridinecarboxylic acids by interaction of the cyanopyridines with NH3 (I). Interaction of 2,6-dicyanopyridine (II) and I gave the tetrazole analog (III) of dipicolinic acid. Hydrogenation of the tetrazolylpyridines gave the corresponding 5-tetrazolylpiperidines, the analogs of the several isomeric piperidinecarboxylic acids. 2-Cyanopyridine (26 g.), 20 g. AcOH, and 22 g. NaN3 refluxed 4 days in 100 ml. BuOH, heated 2 days with a further 5 g. NaN3 and 10 g. AcOH (in other experiments 3- and 4-day heating periods gave approx. the same yields), the mixture diluted with 300 ml. H2O, the BuOH removed, the solution acidified, and the product separated gave 33.4 g. 5-(2-pyridyl)tetrazole (IV), m. 211-11.5° (decomposition) (H2O). Similarly, 3-cyanopyridine and I gave 91% 5-(3-pyridyl)tetrazole (V), m. 234-5° (decomposition) (H2O). Likewise, 4-cyanopyridine and I gave 93% 5-(4-pyridyl)tetrazole (VI), m. 253-4° (decomposition). II (27.5 g.) in 100 ml. BuOH refluxed 2 days with 38.2 g. NaN3 and 38 ml. AcOH then 2 days with 10 g. NaN3 and 20 ml. AcOH gave 45.6 g. III, m. 290° (decomposition)(H2O). IV (11 g.) in 150 ml. AcOH shaken 24 hrs. at 50 lb./sq. in. with 250 mg. PtO2 and H gave 10.5 g. 5-(2-piperidyl)tetrazole, m. 287° (decomposition); acetyl derivative m. 135.5-6.5° (H2O). For preparative purposes it was advantageous to form the acetyl derivative directly by hydrogenation of IV and after removal of the catalyst it was treated with Ac2O to give an over-all yield of 84%. V similarly hydrogenated gave an almost quant. yield of 5-(3-piperidyl)tetrazole, m. 296-7°(H2O); acetyl derivative m. 170-1° (iso-PrOH). VI also gave 86% 5-(4-piperidyl)tetrazole, prisms, not decomposing below 370°; acetyl derivative m. 156.5-7.5° (iso-PrOH).

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis