Category: 31181-89-2

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 31181-89-2, is researched, Molecular C6H4ClNO, about Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes, the main research direction is secondary alc preparation chemoselective hydroxylation deuteration heterobenzylic methylenes.Application In Synthesis of 5-Chloropicolinaldehyde.

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcs. avoiding overoxidn. to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcs. (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Category: chiral-phosphine-ligands. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Chloropicolinaldehyde, is researched, Molecular C6H4ClNO, CAS is 31181-89-2, about Synthesis and SAR of 1,2,3,4-Tetrahydroisoquinoline-Based CXCR4 Antagonists. Author is Wilson, Robert J.; Jecs, Edgars; Miller, Eric J.; Nguyen, Huy H.; Tahirovic, Yesim A.; Truax, Valarie M.; Kim, Michelle B.; Kuo, Katie M.; Wang, Tao; Sum, Chi Shing; Cvijic, Mary E.; Paiva, Anthony A.; Schroeder, Gretchen M.; Wilson, Lawrence J.; Liotta, Dennis C..

CXCR4 is the most common chemokine receptor expressed on the surface of many cancer cell types. In comparison to normal cells, cancer cells overexpress CXCR4, which correlates with cancer cell metastasis, angiogenesis, and tumor growth. CXCR4 antagonists can potentially diminish the viability of cancer cells by interfering with CXCL12-mediated pro-survival signaling and by inhibiting chemotaxis. Herein, a series of CXCR4 antagonists, i.e. I, are described that are derived from (S)-5,6,7,8-tetrahydroquinolin-8-amine that has prevailed in the literature. This series removes the rigidity and chirality of the tetrahydroquinoline providing 2-(aminomethyl)pyridine analogs, which are more readily accessible and exhibit improved liver microsomal stability. The medicinal chem. strategy and biol. properties are described.

Here is just a brief introduction to this compound(31181-89-2)Category: chiral-phosphine-ligands, more information about the compound(5-Chloropicolinaldehyde) is in the article, you can click the link below.

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Recommanded Product: 5-Chloropicolinaldehyde. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Chloropicolinaldehyde, is researched, Molecular C6H4ClNO, CAS is 31181-89-2, about Palladium-Catalyzed Hydrocarbonylative Cyclization Enabled by Formal Insertion of Aromatic C=N Bonds into Pd-Acyl Bonds. Author is Zhou, Xibing; Chen, Anrong; Du, Wei; Wang, Yawen; Peng, Yu; Huang, Hanmin.

An efficient new formal insertion strategy via combination of reductive elimination and oxidative addition sequence was reported, in which the transient N-acyliminium ions formed via hydrocarbonylation function as key intermediates. This strategy has enabled a novel palladium-catalyzed hydrocarbonylative cyclization of azaarene-tethered alkenes or dienes via sequential insertion of a C=C bond, CO, and a C=N bond into palladium-hydride bonds. This method provides a new and highly efficient synthetic approach to quinolizinones and its derivatives with extended π-conjugated systems, possessing tunable emission wavelengths and good photoluminescence capabilities.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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, Research Support, Non-U.S. Gov’t, Bioconjugate Chemistry called Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis, Author is Li, Jian-Yuan; Miklossy, Gabriella; Modukuri, Ram K.; Bohren, Kurt M.; Yu, Zhifeng; Palaniappan, Murugesan; Faver, John C.; Riehle, Kevin; Matzuk, Martin M.; Simmons, Nicholas, which mentions a compound: 31181-89-2, SMILESS is O=CC1=NC=C(Cl)C=C1, Molecular C6H4ClNO, SDS of cas: 31181-89-2.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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: 5-Chloropicolinaldehyde, is researched, Molecular C6H4ClNO, CAS is 31181-89-2, about Design, synthesis and biological activity evaluation of a new class of 2,4-thiazolidinedione compounds as insulin enhancers.Synthetic Route of C6H4ClNO.

Diabetes mellitus (DM) is a global disease with a high incidence of type 2 diabetes. Current studies have shown that insulin enhancers play an important role in the treatment of type 2 diabetes and have great importance in the improvement of type 2 diabetes. In this research, Rosiglitazone was taken as the lead compound, and the structure was modified by using the bioisostere principle, and a new class of 2,4-thiazolanedione compound was designed and synthesized. The novel series of compounds were studied for their biol. activities in vitro and in vivo. In vitro tests, the biol. activities showed that the target compounds have good selective activation of peroxisome-proliferator-activated receptor γ (PPARγ), such as the compounds , , , and , especially the compound to PPARγ was EC50 = 0.03 ± 0.01 μmol/L in vitro. Then, in vivo biol. activities’ test results showed that the tendency of increasing in blood sugar had an obvious inhibiting effect, and had a significant insulin hypoglycemic effect of enhancing and extending the exogenous. In addition, the results of cytotoxicity tests and acute toxicity tests (LD50) showed that these compounds belong to the low toxicity compounds

From this literature《Design, synthesis and biological activity evaluation of a new class of 2,4-thiazolidinedione compounds as insulin enhancers》,we know some information about this compound(31181-89-2)Synthetic Route of C6H4ClNO, but this is not all information, there are many literatures related to this compound(31181-89-2).

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Chloropicolinaldehyde(SMILESS: O=CC1=NC=C(Cl)C=C1,cas:31181-89-2) is researched.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane. The article 《Construction of Protoberberine Alkaloid Core through Palladium Carbene Bridging C-H Bond Functionalization and Pyridine Dearomatization》 in relation to this compound, is published in ACS Catalysis. Let’s take a look at the latest research on this compound (cas:31181-89-2).

Compounds, e.g. I with a pyridoisoquinolinone core often appear as members of the protoberberine alkaloid family. Traditional methods to construct this framework normally rely on manipulation of sophisticated reactants. Herein, a palladium-catalyzed reaction of readily available pyridotriazoles and o-bromo/pseudohalo benzaldehydes is described, which provides a modular approach to pyridoisoquinolinone derivatives This methodol. provides a concise synthetic route to prepare protoberberine-type alkaloids. The role of pyridotriazole is 2-fold, acting as a relay reagent to promote C-H bond functionalization and undergoing pyridine dearomatization to construct the polycyclic system.

From this literature《Construction of Protoberberine Alkaloid Core through Palladium Carbene Bridging C-H Bond Functionalization and Pyridine Dearomatization》,we know some information about this compound(31181-89-2)Reference of 5-Chloropicolinaldehyde, but this is not all information, there are many literatures related to this compound(31181-89-2).

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Al-Khawaldeh, Islam; Al Yasiri, Mohammed J.; Aldred, Gregory G.; Basmadjian, Christine; Bordoni, Cinzia; Harnor, Suzannah J.; Heptinstall, Amy B.; Hobson, Stephen J.; Jennings, Claire E.; Khalifa, Shaimaa; Lebraud, Honorine; Martin, Mathew P.; Miller, Duncan C.; Shrives, Harry J.; de Souza, Joao V.; Stewart, Hannah L.; Temple, Max; Thomas, Huw D.; Totobenazara, Jane; Tucker, Julie A.; Tudhope, Susan J.; Wang, Lan Z.; Bronowska, Agnieszka K.; Cano, Celine; Endicott, Jane A.; Golding, Bernard T.; Hardcastle, Ian R.; Hickson, Ian; Wedge, Stephen R.; Willmore, Elaine; Noble, Martin E. M.; Waring, Michael J. published the article 《An Alkynylpyrimidine-Based Covalent Inhibitor That Targets a Unique Cysteine in NF-κB-Inducing Kinase》. Keywords: cancer NIK covalent inhibitor SAR cysteine traps alkynyl heterocycles.They researched the compound: 5-Chloropicolinaldehyde( cas:31181-89-2 ).Product Details of 31181-89-2. 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:31181-89-2) here.

NF-κB-inducing kinase (NIK) is a key enzyme in the noncanonical NF-κB pathway, of interest in the treatment of a variety of diseases including cancer. Validation of NIK as a drug target requires potent and selective inhibitors. The protein contains a cysteine residue at position 444 in the back pocket of the active site, unique within the kinome. Anal. of existing inhibitor scaffolds and early structure-activity relationships (SARs) led to the design of C444-targeting covalent inhibitors based on alkynyl heterocycle warheads. Mass spectrometry provided proof of the covalent mechanism, and the SAR was rationalized by computational modeling. Profiling of more potent analogs in tumor cell lines with constitutively activated NIK signaling induced a weak antiproliferative effect, suggesting that kinase inhibition may have limited impact on cancer cell growth. This study shows that alkynyl heterocycles are potential cysteine traps, which may be employed where common Michael acceptors, such as acrylamides, are not tolerated.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Chan, Yuk-Cheung; Sak, Marcus H.; Frank, Scott A.; Miller, Scott J. published the article 《Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes》. Keywords: heterocyclic tetrahydro carboline preparation enantioselective; benzylindolyl ethanamine carboxaldehyde Pictet Spengler squaramide carboxylic acid catalyst; Pictet-Spengler; cooperative catalysis; heterocycles; hydrogen bond donors; peptides.They researched the compound: 5-Chloropicolinaldehyde( cas:31181-89-2 ).Application In Synthesis of 5-Chloropicolinaldehyde. 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:31181-89-2) here.

Herein an organocatalytic enantioselective functionalization of heterocyclic carboxaldehydes RCHO (R = Ph, pyridin-3-yl, 1H-imidazol-2-yl, etc.) via the Pictet-Spengler reaction was reported. Through careful pairing of novel squaramide and Bronsted acid catalysts, this method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated β-(tetrahydro)carbolines I (R1 = Bn, 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, etc.) in good yield and enantioselectivity. Careful selection of carboxylic acid co-catalyst is essential for toleration of a variety of regioisomeric heterocycles I. Utility is demonstrated via the three-step stereoselective preparation of pyridine-containing analogs I (R = 5-chloropyridin-2-yl; R1 = 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, 2-carboxyethyl, carboxymethyl) of potent selective estrogen receptor downregulator and U.S. FDA approved drug Tadalafil.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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, Angewandte Chemie, International Edition called Complementing Pyridine-2,6-bis(oxazoline) with Cyclometalated N-Heterocyclic Carbene for Asymmetric Ruthenium Catalysis, Author is Li, Long; Han, Feng; Nie, Xin; Hong, Yubiao; Ivlev, Sergei; Meggers, Eric, which mentions a compound: 31181-89-2, SMILESS is O=CC1=NC=C(Cl)C=C1, Molecular C6H4ClNO, Application of 31181-89-2.

A strategy for expanding the utility of chiral pyridine-2,6-bis(oxazoline) (pybox) ligands for asym. transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asym. induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N-heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chem., including ring contraction to chiral 2H-azirines (up to 97% ee with 2000 TON) and enantioselective C(sp3)-H aminations (up to 97% ee with 50 TON).

In some applications, this compound(31181-89-2)Application of 31181-89-2 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Total Synthesis of (-)-Maximiscin, Author is McClymont, Kyle S.; Wang, Feng-Yuan; Minakar, Amin; Baran, Phil S., which mentions a compound: 31181-89-2, SMILESS is O=CC1=NC=C(Cl)C=C1, Molecular C6H4ClNO, Category: chiral-phosphine-ligands.

A short, enantioselective synthesis of (-)-maximiscin (I), a structurally intriguing metabolite of mixed biosynthetic origin, is reported. A retrosynthetic anal. predicated on maximizing ideality and efficiency led to several unusual disconnections and tactics. Formation of the central highly oxidized pyridone ring through a convergent coupling at the end of the synthesis simplified the route considerably. The requisite building blocks could be prepared from feedstock materials (derived from shikimate and mesitylene). Strategies rooted in hidden symmetry recognition, C-H functionalization, and radical retrosynthesis played key roles in developing this concise route.

In some applications, this compound(31181-89-2)Category: chiral-phosphine-ligands is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate