Category: iodides-buliding-blocks

Characterization of a Structural Leoligin Analog as Farnesoid X Receptor Agonist and Modulator of Cholesterol Transport was written by Ladurner, Angela;Linder, Thomas;Wang, Limei;Hiebl, Verena;Schuster, Daniela;Schnuerch, Michael;Mihovilovic, Marko D.;Atanasov, Atanas G.;Dirsch, Verena M.. And the article was included in Planta Medica in 2020.Application of 5460-32-2 This article mentions the following:

The ligand-activated farnesoid X receptor is an emerging therapeutic target for the development of drugs against metabolic syndrome-related diseases. In this context, selective bile acid receptor modulators represent a novel concept for drug development. Selective bile acid receptor modulators act in a target gene- or tissue-specific way and are therefore considered less likely to elicit unwanted side effects. Based on leoligin, a lignan-type secondary plant metabolite from the alpine plant Leontopodium nivalessp. alpinum, 168 synthesized structural analogs were screened in a farnesoid X receptor in silicopharmacophore-model. Fifty-six virtual hits were generated. These hits were tested in a cell-based farnesoid X receptor transactivation assay and yielded 7 farnesoid X receptor-activating compounds The most active one being LT-141A, with an EC ₅₀of 6μM and an E _maxof 4.1-fold. This analog did not activate the G protein-coupled bile acid receptor, TGR5, and the metabolic nuclear receptors retinoid X receptor α, liver X receptors α/ β, and peroxisome proliferator-activated receptors β/ γ. Investigation of different farnesoid X receptor target genes characterized LT-141A as selective bile acid receptor modulators. Functional studies revealed that LT-141A increased cholesterol efflux from THP-1-derived macrophages viaenhanced ATP-binding cassette transporter 1 expression. Moreover, cholesterol uptake in differentiated Caco-2 cells was significantly decreased upon LT-141A treatment. In conclusion, the leoligin analog LT-141A selectively activates the nuclear receptor farnesoid X receptor and has an influence on cholesterol transport in 2 model systems. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Application of 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Application of 5460-32-2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Intramolecular Pd-Catalyzed Arylation of 1-Amidosugars: A New Route to N-Glycosyl Quinolin-2-ones was written by Luong, Thi Thanh Huyen;Brion, Jean-Daniel;Lescop, Ewen;Alami, Mouad;Messaoudi, Samir. And the article was included in Organic Letters in 2016.Related Products of 877264-43-2 This article mentions the following:

The synthesis of N-glycosylated quinolin-2-ones via an intramol. N-arylation of glycosylamides is reported. The coupling involves the use of only Pd(OAc)₂ as the catalyst and nBu₄NOAc as the base in 1,4-dioxane. This versatile approach allows the synthesis of various N-glycosylated quinolin-2-ones with exclusive α or β selectivity. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Related Products of 877264-43-2).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Related Products of 877264-43-2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate was written by Sandmann, Nikolas;Defayay, Denise;Hepp, Alexander;Mueller, Jens. And the article was included in Journal of Inorganic Biochemistry in 2019.SDS of cas: 15813-09-9 This article mentions the following:

The use of imidazole-4-carboxylate (X) as an artificial nucleobase in metal-mediated base pairing is reported. Towards this end, the corresponding deoxyribonucleoside was synthesized and structurally characterized as its sodium salt (sodium 1,2-dideoxy-1-(4-carboxyimidazol-1-yl)-D-ribofuranose). The deoxyribonucleoside was incorporated into different DNA duplexes (parallel-stranded and antiparallel-stranded), and their Cu(II)- and Ag(I)-binding behavior was investigated. It was shown that both X-Cu(II)-X and X-Ag(I)-X base pairs can be formed, with the former being more stabilizing than the latter. The formation of an X-Cu(II)-X base pair is accompanied by an increase in the duplex melting temperature of approx. 20 °C for antiparallel-stranded duplexes and of 12 °C for the parallel-stranded duplex under investigation. Imidazole-4-carboxylate represents the first imidazole-based nucleoside for Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X-Cu(II)-X and X-Ag(I)-X base pairs are proposed, too, based on mol. structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9SDS of cas: 15813-09-9).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.SDS of cas: 15813-09-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Copper-Catalyzed Azide-Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles was written by Liu, Xin;Wang, Ze-Shu;Zhai, Tong-Yi;Luo, Chen;Zhang, Yi-Ping;Chen, Yang-Bo;Deng, Chao;Liu, Rai-Shung;Ye, Long-Wu. And the article was included in Angewandte Chemie, International Edition in 2020.Category: iodides-buliding-blocks This article mentions the following:

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles, e.g., I, in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asym. azide-ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asym. azide-alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theor. calculations In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Category: iodides-buliding-blocks).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical was written by Artaryan, Alexander;Mardyukov, Artur;Kulbitski, Kseniya;Avigdori, Idan;Nisnevich, Gennady A.;Schreiner, Peter R.;Gandelman, Mark. And the article was included in Journal of Organic Chemistry in 2017.Application of 10297-05-9 This article mentions the following:

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Application of 10297-05-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Migratory Hydrogenation of Terminal Alkynes by Base/Cobalt Relay Catalysis was written by Liu, Xufang;Liu, Bingxue;Liu, Qiang. And the article was included in Angewandte Chemie, International Edition in 2020.HPLC of Formula: 85356-68-9 This article mentions the following:

Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9HPLC of Formula: 85356-68-9).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.HPLC of Formula: 85356-68-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Phenylpropiolic acids. VIII. Self-condensation of 3-halo-4-methoxyphenylpropiolic acids was written by Baddar, Fawzi G.;Moussa, G. E. M.;Omar, M. T.. And the article was included in Journal of the Chemical Society [Section] C: Organic in 1968.COA of Formula: C8H7IO2 This article mentions the following:

3-Halo-4-methoxyphenylpropiolic acids are converted by Ac2O into a mixture of 6- and 8-halo-7-methoxy-1-(3-halo-4-methoxyphenyl)naphthalene-2,3-dicarboxylic anhydrides. The structure of 6-bromo-7-methoxy-1-(3-bromo-4 – methoxyphenyl)naphthalene-2,3-dicarboxylic anhydride was established by its conversion into the corresponding 6,7-dimethoxy derivative The structure of the remaining anhydrides were established by ir and uv spectroscopy. The anhydrides are isomerized by AlCl3 to the corresponding 7H-benzo[c]fluoren-7-one. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6COA of Formula: C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.COA of Formula: C8H7IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Modular C-H Functionalization Cascade of Aryl Iodides was written by Shi, Hang;Babinski, David J.;Ritter, Tobias. And the article was included in Journal of the American Chemical Society in 2015.HPLC of Formula: 133232-56-1 This article mentions the following:

We report the first example of ipso-borylation for the modular 1,2-bisfunctionalization of aryl iodides via C-H functionalization. The carbon-boron bond is used as a lynch pin to access ipso carbon-carbon, carbon-nitrogen, carbon-oxygen, and carbon-halogen (Cl, Br, I) bonds. The utility of our methodol. is illustrated through quick, modular syntheses of the pharmaceuticals Abilify and Flunixin. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1HPLC of Formula: 133232-56-1).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.HPLC of Formula: 133232-56-1

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electrophilic aromatic substitution. 26. Regioselective halo- and carbodesilylation of (trimethylsilyl)-1-methylpyrazoles was written by Effenberger, Franz;Krebs, Andreas. And the article was included in Journal of Organic Chemistry in 1984.SDS of cas: 34091-51-5 This article mentions the following:

The isomeric 3-, 4-, and 5-(trimethylsilyl)- (I) as well as the 3,4- (II), 3,5- (III), and 4,5-bis(trimethylsilyl)-1-methylpyrazoles (IV) are obtained by methylation of the corresponding (trimethylsilyl)-1H-pyrazoles or by silylation of Grignard or lithio derivatives of appropriate 1-methylpyrazoles with ClSiMe₃. II and IV are halodesilylated regioselectively in the 4-position by Br or ICl, yielding V (R = SiMe₃, R¹ = H; R = H, R¹ = SiMe₃). With addnl. Br, these monobromo compounds suffer exclusively bromodesilylation to give 3,4- and 4,5-dibromo-1-methylpyrazole. These findings are in accord with the electrophilic substitution reactivity indexes for 1-methylpyrazole and with the ipso-directing influence of the Me₃Si group. The reaction of II with I₂, unexpectedly, occurs preferentially at the 3-position. Regioselective carbodesilylation in the 5-position is observed in the fluoride-catalyzed reactions of I, III, and IV with electrophiles. The high regiospecificity of this reaction is rationalized in terms of carbanion stabilization at the individual pyrazole positions. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5SDS of cas: 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.SDS of cas: 34091-51-5

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Selective C(sp³)-H and C(sp²)-H Fluorination of Alcohols Using Practical Auxiliaries was written by Mao, Yang-Jie;Lou, Shao-Jie;Hao, Hong-Yan;Xu, Dan-Qian. And the article was included in Angewandte Chemie, International Edition in 2018.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene This article mentions the following:

Selective introduction of fluorine into mols. by the cleavage of inert C-H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcs. in organic chem. as the most ubiquitous building blocks, a versatile and selective C(sp³)-H and C(sp²)-H fluorination of simple alcs., enabled by novel designed exo-directing groups, is described. C(sp²)-H bond fluorination was achieved by using a simple acetone oxime as auxiliary, whereas a new, modular and easily accessible bidentate auxiliary was developed for the efficient and site-selective fluorination of various primary Me, methylene, and benzylic C(sp³)-H bonds. Fluorinated alcs. can readily be accessed by the removal of auxiliaries, and significantly expands the synthetic prospect of the present procedure. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com