Tag: 100-200

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition was written by Yu, Xiaolong;Zhao, Haonan;Li, Ping;Koh, Ming Joo. And the article was included in Journal of the American Chemical Society in 2020.Related Products of 85838-94-4 This article mentions the following:

The catalytic isomerization of C-C double bonds is an indispensable chem. transformation used to deliver higher-value analogs and has important utility in the chem. industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C=C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/灏?hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biol. active entities can be obtained. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Related Products of 85838-94-4).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). Pyridine derivatives are also useful as small-molecule 浼?helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Related Products of 85838-94-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthesis of 3,4-diaminothiophenes was written by Tominaga, Yoshinori;Fujito, Hiroshi;Matsuda, Yoshiro;Kobayashi, Goro. And the article was included in Heterocycles in 1977.SDS of cas: 17281-59-3 This article mentions the following:

Thiophenediamines I (R = CN, CONH₂, CO₂Et, Bz) were prepared by treating R¹CH₂CNCl^– (R¹ = pyridinio) with CS₂-NaOH, treating R¹C(CN):C(SNa)S^– with R²CH₂R (R² = Cl, Br), cyclizing R¹C(CN):C(S^–)SCH₂R with NEt₃, methylating ylides II (R³ = S^–), treating II (R³ = SMe) with MeNH₂-HCl and neutralizing. I condensed with R⁴COCOR⁴ (R⁴ = H, Me, Ph) to give the thienopyrazines III. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3SDS of cas: 17281-59-3).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the 锜?bonds. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C閳ユ弻 in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.SDS of cas: 17281-59-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Understanding the Effects of Preorganization, Rigidity, and Steric Interactions in Synthetic Barbiturate Receptors was written by McGrath, Jacqueline M.;Pluth, Michael D.. And the article was included in Journal of Organic Chemistry in 2014.Name: N-(6-Aminopyridin-2-yl)acetamide This article mentions the following:

Synthetic barbiturate receptors have been utilized for many applications due to their high binding affinities for complementary guests. Although interest in this class of receptors spans from supramol. to materials chem., the effects of receptor steric bulk and preorganization on guest binding affinity has not been studied systematically. To investigate the roles that steric bulk and preorganization play in guest binding, we prepared a series of 12 deconstructed Hamilton receptors with varying degrees of steric bulk and preorganization. Both diethylbarbital and 3-methyl-7-propylxanthine were investigated as guests for the synthetic receptors. The stoichiometry of guest binding was investigated using Job plots for each host-guest pair, and ¹H NMR titrations were performed to measure the guest binding affinities. To complement the solution-state studies, DFT calculations at the B3LYP/6-31+G-(d,p) level of theory employing the IEF-PCM CHCl₃ solvation model were also performed. Calculated guest binding energies correlated well with the exptl. findings and provided addnl. insight into the factors influencing guest binding. Taken together, the results presented highlight the interplay between preorganization and steric interactions in establishing favorable interactions for self-assembled hydrogen-bonded systems. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3Name: N-(6-Aminopyridin-2-yl)acetamide).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Name: N-(6-Aminopyridin-2-yl)acetamide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analysis of Hydrogen Bonding Network in the Systems Containing Chloride-Based Ionic Liquids with Cellulose/Cellobiose by Fourier-Transform Infrared Spectroscopy was written by Kashirskii, D. A.;Sashina, E. S.;Artamonova, T. V.;Myznikov, L. V.. And the article was included in Russian Journal of General Chemistry in 2018.Application of 125652-55-3 This article mentions the following:

Hydrogen bonds formed upon dissolution of cellulose and cellobiose in ionic liquids, 1-butyl-3-methylpyridinium and 1-butyl-3-methylimidazolium chlorides, were analyzed and characterized by means of Fourier-transform IR spectroscopy and quantum-chem. calculation The obtained data were used for assignment of absorption bands of individual OH groups and determination of hydrogen bonds energy in the solutions In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Application of 125652-55-3).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of 閳?8.7 鑴?10閳? cm3璺痬ol閳?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ璺痬ol閳? in the liquid phase and 140.4 kJ璺痬ol閳? in the gas phase. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Application of 125652-55-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of 2-pyridinamines and their alkyl derivatives from 2-cyanopyridines was written by Dai, Liyan;Fang, Jun;Wang, Xiaozhong;Chen, Yingqi. And the article was included in Huagong Xuebao (Chinese Edition) in 2007.Recommanded Product: 3,6-Dimethyl-2-pyridinamine This article mentions the following:

The preparation of a series of 2-pyridinamines and their alkyl derivatives is described. The target compounds are synthesized starting from corresponding 2-cyanopyridines, via incomplete hydrolysis in the presence of hydrogen peroxide in the dilute alk. mixture of acetone-2% sodium hydroxide solution, and Hoffmann degradation reaction with freshly made NaBrO. This route is of industrial value because of cheap and readily available materials, moderate reaction conditions and convenient operations. In the experiment, the researchers used many compounds, for example, 3,6-Dimethyl-2-pyridinamine (cas: 823-61-0Recommanded Product: 3,6-Dimethyl-2-pyridinamine).

3,6-Dimethyl-2-pyridinamine (cas: 823-61-0) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: 3,6-Dimethyl-2-pyridinamine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalized side chains and anions of ionic liquids on acetylcholinesterase was written by Arning, Juergen;Stolte, Stefan;Boeschen, Andrea;Stock, Frauke;Pitner, William-Robert;Welz-Biermann, Urs;Jastorff, Bernd;Ranke, Johannes. And the article was included in Green Chemistry in 2008.Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride This article mentions the following:

To contribute to a deeper insight into the hazard potential of ionic liquids to humans and the environment, an acetylcholinesterase (AchE) inhibition screening assay was used to identify toxicophore substructures and interaction potentials mediating enzyme inhibition. The pos. charged nitrogen atom, a widely delocalized aromatic system, and the lipophilicity of the side chains connected to the cationic head groups can be identified as the key structural elements in binding to the enzymes active site. With respect to this, the dimethylaminopyridinium, the quinolinium and the pyridinium head groups exhibit a very strong inhibitory potential to the enzyme with IC₅₀ values around 10 娓璏. In contrast, the polar and non-aromatic morpholinium head group is found to be only weakly inhibiting to the enzyme activity, with IC₅₀ values > 500 娓璏. The introduction of polar hydroxy, ether or nitrile functions into the alkyl side chain is shown to be a potent structural alteration to shift the corresponding ionic liquids to a lower inhibitory potential. Supporting this fact, for a series of imidazolium cations, a QSAR correlation was set up by the linear regression of the log IC₅₀ vs. the logarithm of the HPLC-derived lipophilicity parameter k₀. Addnl., a broad set of anion species (inorganic, organic and complex borate anions), commonly used as ionic liquid counterions, was tested and the vast majority exhibited no effect on AchE. Only the fluoride and fluoride containing anion species which readily undergo hydrolytic cleavage can be identified to act as AchE inhibitors. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Application In Synthesis of 1-Butyl-3-methylpyridinium Chloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rhodium-Catalyzed Regioselective Synthesis of Isoindolium Salts from 2-Arylpyridines and Alkenes in Aqueous Medium under Oxygen was written by Upadhyay, Nitinkumar Satyadev;Jayakumar, Jayachandran;Cheng, Chien-Hong. And the article was included in Advanced Synthesis & Catalysis in 2016.Recommanded Product: 2-(m-Tolyl)pyridine This article mentions the following:

A highly regioselective synthesis of pyrido[2,1-a]isoindolium salts, e.g., I (X-rays single crystal structure shown), from 2-arylpyridines and two equivalent of electron-deficient alkenes catalyzed by rhodium is demonstrated. The reaction was carried out in aqueous medium at 110 鎺矯 using inexpensive oxygen as oxidant. Reverse aza-Michael addition of the isoindolium salt occurs when the salt was treated with base to give a 灏?disubstituted alkene product. A reaction mechanism involving an ortho C-H olefination of 2-arylpyridine by alkene, intramol. aza-Michael addition, deprotonation at the 灏?carbon of the alkene fragment followed by another Michael addition to give the final product is proposed. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Recommanded Product: 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the 锜?bonds. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C閳ユ弻 in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Recommanded Product: 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Utilizing Selective Chlorination to Synthesize New Triangulenium Dyes was written by Jensen, Jesper Dahl;Bisballe, Niels;Kacenauskaite, Laura;Thomsen, Maria Storm;Chen, Junsheng;Hammerich, Ole;Laursen, Bo W.. And the article was included in Journal of Organic Chemistry in 2021.Quality Control of Pyridinehydrochloride This article mentions the following:

Functionalization of new sites on the triangulenium structure has been achieved by early stage chlorination with N-chlorosuccinimide (NCS), giving rise to two new triangulenium dyes (1 and 3). By introducing the chlorine functionalities in the acridinium precursor, positions complementary to those previously accessed by electrophilic aromatic substitution on the final dyes are accessed. The chlorination is selective, giving only one regioisomer for both mono- and dichlorination products. For the monochlorinated acridinium compound a highly selective ring-closing reaction was discovered, generating a single regioisomer of the cationic [4]helicene product. Further investigations into the mechanism of [4]helicene formation lead to the first isolation of the previously proposed intermediate of the two-step S_NAr reaction, key to all aza-bridged triangulenium and helicenium systems. Late-stage functionalization of DAOTA⁺ with NCS gave rise to a different dichlorinated compound (2). The fully ring closed chlorinated triangulenium dyes 1, 2 and 3 show red shift in absorption and emission, while maintaining relatively high fluorescence quantum yields of 36%, 26%, and 41%, and long fluorescence lifetimes of 15 ns, 12.5 and 16 ns, resp. Cyclic voltammetry shows that chlorination of the triangulenium dyes significantly lowers reduction potentials and thus allows for efficient tuning of redox and photoredox properties. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Quality Control of Pyridinehydrochloride).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Quality Control of Pyridinehydrochloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Preparation of new nitrogen-bridged heterocycles. 42. Synthesis and the reaction of pyridinium N-ylides using bifunctional ethyl thiocyanatoacetates was written by Kakehi, Akikazu;Ito, Suketaka;Hashimoto, Yasunobu. And the article was included in Bulletin of the Chemical Society of Japan in 1996.Formula: C7H7ClN2 This article mentions the following:

Various pyridinium (monosubstituted methylide)s I (R², R³, R⁴ = H, Me; R⁵ = cyano, CO₂Et, COMe, COPh) were smoothly attached to the cyano group in Et thiocyanatoacetate or Et 2-thiocyanatopropionate to afford the corresponding pyridinium (substituted cyanomethylide)s II in low-to-moderate yields, while pyridinium (unsubstituted amidate)s III (R¹, R², R³ = H, Me) reacted with the ester carbonyl group in the same reagents to give pyridinium (thiocyanatoacetato)- or (2-thiocyanatopropiono)amidates IV in considerable yields. The 1,3-dipolar cycloadditions of some pyridinium (unsym. substituted cyanomethylide)s with di-Me acetylenedicarboxylate (DMAD) in various solvents afforded only di-Me 3-cyanoindolizine-1,2-dicarboxylate, except for a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium tert-butoxide, gave new bicyclic mesoionic compounds, N-[2-(1,3,4-thiadiazolo[3,2-a]pyridinio)]acetamidate derivatives V, in moderate yields. The intermediacy of N-[1-(2-thiocyanatopyridinio)]acetamidates in the formation reactions of the latter compounds was also proven by independent syntheses. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Formula: C7H7ClN2).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the 锜?bonds. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Formula: C7H7ClN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem