Month: February 2023

Pd-Catalyzed Regio- and Stereoselective sp³ C-H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications was written by Ha, Hyeonbin;Choi, Ho Jeong;Park, Hahyoun;Gwon, Yunyeong;Lee, Jiin;Kwak, Jaesung;Kim, Min;Jung, Byunghyuck. And the article was included in European Journal of Organic Chemistry in 2021.Name: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

The Pd-catalyzed γ-position sp³-C-H arylation of primary amines bearing an aliphatic chain or cycloalkyl substituent and related mechanistic studies are disclosed. 3-Bromo-2-hydroxybenzaldehyde plays a key role in γ-position sp³-C-H arylation as a transient directing group (TDG) to assist the regio- and stereoselective C-H activation of a Pd catalyst, and the development of a tandem reaction to transform 1°-amines into γ-aryl-substituted ketones demonstrates synthetic utility. D. functional theory (DFT)-based calculations revealed the detailed reaction mechanism and the origins of the high selectivity (γ-position and cis-only). The X-ray crystal structure of the isolated endo-palladacycle intermediate supported the DFT results, and a kinetic isotope experiment confirmed the results of DFT calculations indicating that the C-H activation step via simultaneous palladation and deprotonation is rate-determining In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Name: 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Name: 4-Iodo-1,2-dimethoxybenzene

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

A general synthetic route towards bastadins. Part 1: synthesis of the eastern part of bastadins 4-16 was written by Couladouros, Elias A.;Moutsos, Vassilios I.. And the article was included in Tetrahedron Letters in 1999.Formula: C8H7IO2 This article mentions the following:

A general synthetic route for the construction of the eastern part of the macrocyclic bastadins 4-16 is presented. The brominated biaryl ethers are synthesized using the iodonium salt method. The synthesis is accomplished within 18 steps in 15.5% overall yield. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Formula: C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Formula: C8H7IO2

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

New polyhydroxylated flavon-3-ols and 3-hydroxy-2-styrylchromones: synthesis and ROS/RNS scavenging activities was written by Sousa, Joana L. C.;Proenca, Carina;Freitas, Marisa;Fernandes, Eduarda;Silva, Artur M. S.. And the article was included in European Journal of Medicinal Chemistry in 2016.COA of Formula: C8H9IO2 This article mentions the following:

New polyhydroxylated flavon-3-ols I (R = OH, OMe; R¹ = OH, OMe) and 3-hydroxy-2-styrylchromones II were prepared and assessed as reactive oxygen species (ROS) and reactive nitrogen species (RNS) scavengers. The synthetic strategy involved the preparation of 2′-hydroxychalcones (E)-XC(O)CH:CHY [X = 2-HO-3,4-(C₆H₅CH₂O)₂C₆H₂, 2-HO-3,4-(H₃CO)₂C₆H₂; Y = 3,4-(C₆H₅CH₂O)₂C₆H₃, 3,4-(H₃CO)₂C₆H₃] and 2′-hydroxycinnamylidenoacetophenones (E),(E)-XC(O)CH:CHCH:CHY from base-catalyzed aldol reaction of appropriate 2′-hydroxyacetophenones such as 3′,4′-bis(benzyloxy)-2′-hydroxyacetophenone, 2′-hydroxy-3′,4′-dimethoxyacetophenone and benzaldehydes such as 3,4-dimethoxybenzaldehyde, 3,4-bis(benzyloxy)benzaldehyde/cinnamaldehydes such as (E)-3,4-dimethoxycinnamaldehyde, (E)-3,4-bis(benzyloxy)cinnamaldehyde, followed by an Algar-Flynn-Oyamada (AFO) reaction to give the polyalkoxy(flavon-3-ols I and 3-hydroxy-2-styrylchromones II). The last step of this synthetic route consisted of the cleavage of the protecting groups affording the expected polyhydroxylated derivatives I and II. The present work consisted of the study of the in vitro scavenging activities of the synthesized compounds against the most physiol. relevant ROS [superoxide radical (O₂·^–), hydrogen peroxide (H₂O₂), hypochlorous acid (HOCl), singlet oxygen (¹O₂) and peroxyl radical (ROO·)] and RNS [nitric oxide (·NO) and peroxynitrite anion (ONOO^–)]. Generally, all the tested new polyhydroxylated flavon-3-ols I and 3-hydroxy-2-styrylchromones II exhibited scavenging effects dependent on the concentration, and with IC₅₀ values found within the micromolar range. This work allowed the establishment of new structure-activity relationships and brought out the knowledge about the selective choice of a structure depending on the targeted reactive species. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2COA of Formula: C8H9IO2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. 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.COA of Formula: C8H9IO2

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

A facile synthesis of 2-(2-hydroxyethyl)allylsilanes was written by Bardot, Valerie;Remuson, Roland;Gelas-Mialhe, Yvonne;Gramain, Jean-Claude. And the article was included in Synlett in 1996.Application In Synthesis of 3-Iodo-4-methoxybenzaldehyde This article mentions the following:

Indium-mediated allylsilylation of carbonyl compounds provides a facile and efficient route to 2-(2-hydroxyethyl)allylsilanes. For example, 3-iodo-2-(trimethylsilylmethyl)-1-propene reacts with 2,6-dichlorobenzaldehyde in the presence of In powder in DMF to give 90% 2,6-Cl₂C₆H₃CH(OH)CH₂C(:CH₂)CH₂SiMe₃. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Application In Synthesis of 3-Iodo-4-methoxybenzaldehyde).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Application In Synthesis of 3-Iodo-4-methoxybenzaldehyde

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

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols was written by Satkar, Yuvraj;Yera-Ledesma, Luisa F.;Mali, Narendra;Patil, Dipak;Navarro-Santos, Pedro;Segura-Quezada, Luis A.;Ramirez-Morales, Perla I.;Solorio-Alvarado, Cesar R.. And the article was included in Journal of Organic Chemistry in 2019.Safety of 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K₃PO₄. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chem. calculations revealed PhII(OH)·NH₃ to be the most plausible iodinating active species as a reactive “I⁺” synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Safety of 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) 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.Safety of 4-Iodo-1,2-dimethoxybenzene

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

Inhibition of bacteria by 5-fluoronicotinic acid and other analogs of nicotinic acid was written by Streigbtoff, Frank. And the article was included in Journal of Bacteriology in 1963.HPLC of Formula: 15366-65-1 This article mentions the following:

Several compounds related to 5-fluoronicotinic acid (I) have been demonstrated to inhibit Streptococcus spp. (Viridans group), Staphylococcus aureus, Escherichia coli, and Lactobacillus plan- tarum. The most active compounds were I and 5-fluoronicotin- amide (II). The growth of Streptococcus spp. was inhibited more than 5% by 0.05 γ/ml. of I or 0.5 of II. The inhibition of Streptococcus from 1 part of I or II was reversed by 4 and 2 parts of nicotinic acid, resp. The inhibition of E. coli from 100 parts of I or II was reversed by I part of nicotinic acid. Inhibitions by most other active compounds could be reversed by nicotinic acid. In experiments with mice, 8 compounds related to I had activity against Streptococcus pyogenes; I, II, and 5-fluoro-N-dimethyl- aminomethylnicotinamide protected all mice at 83 mg./kg. The action of 200 mg./kg. I was reversed by 20 mg./kg. of nicotinic acid. The activity of I was not increased by modifica- tions at the number 3 or 5 positions on the pyridine ring or by any other structural changes. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1HPLC of Formula: 15366-65-1).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.HPLC of Formula: 15366-65-1

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

From an Eight-Component Self-Sorting Algorithm to a Trisheterometallic Scalene Triangle was written by Mahata, Kingsuk;Saha, Manik Lal;Schmittel, Michael. And the article was included in Journal of the American Chemical Society in 2010.Related Products of 3268-21-1 This article mentions the following:

Using motifs from 3-fold completive self-sorting in an eight-component library, the authors report on the design and fabrication of a fully dynamic trisheterometallic scalene triangle, a demanding supramol. structure that complements the so far known triangular structures. The trisheterometallic scalene triangle complexes have the compositions [CuZn(7)(8)(9)](OTf)₂(PF₆) and [CuHg(7)(8)(9)](ClO₄)₂(PF₆) (7 = (5-(4-(2,9-bis(2,6-dimethoxyphenyl)-1,10-phenanthrolin-3-ylethynyl)phenyl)-10,15,20-trimesitylporphyrinato)zinc, 8 = 4′-(4-(1,10-phenanthrolin-3-ylethynyl)phenyl)-2,2′:6′,2”-terpyridine, 9 = 2-(4-bromo-2,3,5,6-tetramethylphenyl)-9-mesityl-3-((4-(pyridin-4-ylethynyl)-2,3,5,6-tetramethylphenyl)ethynyl)-1,10-phenanthroline). In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Related Products of 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. 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.Related Products of 3268-21-1

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

Adamantyl-Substituted Retinoid-Derived Molecules That Interact with the Orphan Nuclear Receptor Small Heterodimer Partner: Effects of Replacing the 1-Adamantyl or Hydroxyl Group on Inhibition of Cancer Cell Growth, Induction of Cancer Cell Apoptosis, and Inhibition of Src Homology 2 Domain-Containing Protein Tyrosine Phosphatase-2 Activity was written by Dawson, Marcia I.;Xia, Zebin;Jiang, Tao;Ye, Mao;Fontana, Joseph A.;Farhana, Lulu;Patel, Bhaumik;Xue, Li Ping;Bhuiyan, Mohammad;Pellicciari, Roberto;Macchiarulo, Antonio;Nuti, Roberto;Zhang, Xiao-Kun;Han, Young-Hoon;Tautz, Lutz;Hobbs, Peter D.;Jong, Ling;Waleh, Nahid;Chao, Wan-ru;Feng, Gen-Sheng;Pang, Yuhong;Su, Ying. And the article was included in Journal of Medicinal Chemistry in 2008.Recommanded Product: 207115-22-8 This article mentions the following:

(E)-4-[3-(1-Adamantyl)-4′-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell-cycle arrest and apoptosis of leukemia and cancer cells. Studies demonstrated that 3-Cl-AHPC bound to the atypical orphan nuclear receptor small heterodimer partner (SHP). Although missing a DNA-binding domain, SHP heterodimerizes with the ligand-binding domains of other nuclear receptors to repress their abilities to induce or inhibit gene expression. 3-Cl-AHPC analogs having the 1-adamantyl and phenolic hydroxyl pharmacophoric elements replaced with isosteric groups were designed, synthesized, and evaluated for their inhibition of proliferation and induction of human cancer cell apoptosis. Structure-anticancer activity relationship studies indicated the importance of both groups to apoptotic activity. Docking of 3-Cl-AHPC and its analogs to an SHP computational model that was based on the crystal structure of ultraspiracle complexed with 1-stearoyl-2-palmitoylglycero-3-phosphoethanolamine suggested why these 3-Cl-AHPC groups could influence SHP activity. Inhibitory activity against Src homol. 2 domain-containing protein tyrosine phosphatase 2 (Shp-2) was also assessed. The most active Shp-2 inhibitor was found to be the 3′-(3,3-dimethylbutynyl) analog of 3-Cl-AHPC. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Recommanded Product: 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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.Recommanded Product: 207115-22-8

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

Photo-Induced Ruthenium-Catalyzed C-H Arylations at Ambient Temperature was written by Korvorapun, Korkit;Struwe, Julia;Kuniyil, Rositha;Zangarelli, Agnese;Casnati, Anna;Waeterschoot, Marjo;Ackermann, Lutz. And the article was included in Angewandte Chemie, International Edition in 2020.Category: iodides-buliding-blocks This article mentions the following:

Ambient temperature ruthenium-catalyzed C-H arylations were accomplished by visible light without addnl. photocatalysts. The robustness of the ruthenium-catalyzed C-H functionalization protocol was reflected by a broad range of sensitive functional groups and synthetically useful pyrazoles, triazoles and sensitive nucleosides and nucleotides, as well as multifold C-H functionalizations. Biscyclometalated ruthenium complexes were identified as the key intermediates in the photoredox ruthenium catalysis by detailed computational and exptl. mechanistic anal. Calculations suggested that the in situ formed photoactive ruthenium species preferably underwent an inner-sphere electron transfer. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Category: iodides-buliding-blocks).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. 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.Category: iodides-buliding-blocks

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

Oxidative displacement of halogen from alkyl halides by phenyliodine(III) dicarboxylates was written by Gallos, John;Varvoglis, Anastasios. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1983.Reference of 3268-21-1 This article mentions the following:

The reaction of alkyl iodides with aryliodine(III) dicarboxylates gave mainly esters derived through substitution of iodine by an acyloxy group, together with, in some cases, α-iodoalkyl esters. E.g., reaction of PhI(O₂CCF₃)₂ with Me₂CHI in EtOH-free CHCl₃ in the dark at room temperature for 2-8 h gave F₃CCO₂CHMe₂, quant. Reactive bromides and chlorides reacted similarly. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Reference of 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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. 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.Reference of 3268-21-1

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