Tag: 300-400

Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol was written by Simmons, Eric M.;Hartwig, John F.. And the article was included in Nature (London, United Kingdom) in 2012.Application In Synthesis of N,N-Diethyl-4-iodobenzamide This article mentions the following:

New synthetic methods for the catalytic functionalization of C-H bonds have the potential to revolutionize the synthesis of complex mols. However, the realization of this synthetic potential requires the ability to functionalize selectively one C-H bond in a compound containing many such bonds and an array of functional groups. The site-selective functionalization of aliphatic C-H bonds is one of the greatest challenges that must be met for C-H bond functionalization to be used widely in complex-mol. synthesis, and processes catalyzed by transition-metals provide the opportunity to control selectivity. Current methods for catalytic, aliphatic C-H bond functionalization typically rely on the presence of one inherently reactive C-H bond, or on installation and subsequent removal of directing groups that are not components of the desired mol. To overcome these limitations, we sought catalysts and reagents that would facilitate aliphatic C-H bond functionalization at a single site, with chemoselectivity derived from the properties of the catalyst and site-selectivity directed by common functional groups contained in both the reactant and the desired product. Here, we show that the combination of an iridium-phenanthroline catalyst and a dihydridosilane reagent leads to the site-selective γ-functionalization of primary C-H bonds controlled by a hydroxyl group, the most common functional group in natural products. The scope of the reaction encompasses alcs. and ketones bearing many substitution patterns and auxiliary functional groups; this broad scope suggests that this methodol. will be suitable for the site-selective and diastereoselective functionalization of complex natural products. For example, treating (+)-fenchol with [Ir(cod)OMe]₂ and Et₂SiH gave the corresponding diethyl(hydrido)silyl ether, which was cyclized using [Ir(cod)OMe]₂/Me₄phen to give an intermediate oxasiloxane. The latter compound was oxidized under Tamao-Fleming conditions and then diacylated to give hydroxyfenchol diacetate I in 66% yield. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application In Synthesis of N,N-Diethyl-4-iodobenzamide).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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.Application In Synthesis of N,N-Diethyl-4-iodobenzamide

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

Fast Halogenation of Some N-Heterocycles by Means of N,N’-Dihalo-5,5-dimethylhydantoin was written by Sandtorv, Alexander H.;Bjorsvik, Hans-Rene. And the article was included in Advanced Synthesis & Catalysis in 2013.COA of Formula: C3H2I2N2 This article mentions the following:

An instantaneous, selective and high-yielding halogenation process is reported. The method operates with imidazoles, pyrazoles, and indoles under benign reaction conditions. The developed process involves the use of N,N’-dihalo-5,5-dimethylhydantoins (halo = chlorine, bromine, iodine) as halogenation reagents that are activated by catalytic quantities of a strong Bronsted acid. Moreover, the halogenation process is switchable to produce either the mono- or di-halogenated products. Issues related to the reaction mechanism are investigated and a proposal for a reaction mechanism is disclosed. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9COA of Formula: C3H2I2N2).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.COA of Formula: C3H2I2N2

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

Efficient palladium-catalyzed synthesis of unsymmetrical donor-acceptor biaryls and polyaryls was written by Amatore, Christian;Jutand, Anny;Negri, Serge;Fauvarque, Jean Francois. And the article was included in Journal of Organometallic Chemistry in 1990.Recommanded Product: N,N-Diethyl-4-iodobenzamide This article mentions the following:

4,4′-Unsym. substituted biphenyls were synthesized by cross-coupling reactions of substituted aromatic organometallic reagents and aromatic halides catalyzed by palladium complexes. This two-step method from com. available aromatic halides was used for the synthesis of a series of donor/acceptor para-substituted biphenyls, RC₆H₄C₆H₄R¹ (R = electron donor group, R¹ = electron acceptor group), which are of interest as liquid crystal precursors and as having potential in nonlinear optics. Thus, 4-Me₂NC₆H₄ZnCl reacted with 4-BrC₆H₄CN to give 78% 4-Me₂NC₆H₄C₆H₄CN-4′. Biaryls (e.g., I, X = O, S) in which the donor-Ph moiety is replaced by 2-furyl or 2-thienyl were synthesized similarly. The method was also used for the convergent synthesis of previously unreported unsym. substituted polyparaphenylenes 4-R(C₆H₄)_nCN (R = Br, Me₂N, MeS; n = 3, 4). In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Recommanded Product: N,N-Diethyl-4-iodobenzamide).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Recommanded Product: N,N-Diethyl-4-iodobenzamide

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

Programmable synthesis of multiply arylated cubanes through C-H metalation and arylation was written by Okude, Ryo;Mori, Genki;Yagi, Akiko;Itami, Kenichiro. And the article was included in Chemical Science in 2020.Category: iodides-buliding-blocks This article mentions the following:

Cubane (C₈H₈), a cubic alkane, was long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technol., a powerful method for synthesizing diverse cubane derivatives was required. The synthesis of mono-, di-, tri-, and tetra-arylated cubaneS was discussed. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C-H metalation and arylation of cubane. This reaction allows the late-stage and regioselective installation of a wide range of aryl groups, realizing the first programmable synthesis of diverse multiply arylated cubanes. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Category: iodides-buliding-blocks).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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. 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.Category: iodides-buliding-blocks

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

New Diarylmethylpiperazines as Potent and Selective Nonpeptidic δ Opioid Receptor Agonists with Increased In Vitro Metabolic Stability was written by Plobeck, Niklas;Delorme, Daniel;Wei, Zhong-Yong;Yang, Hua;Zhou, Fei;Schwarz, Peter;Gawell, Lars;Gagnon, Helene;Pelcman, Benjamin;Schmidt, Ralf;Yue, Shi Yi;Walpole, Christopher;Brown, William;Zhou, Edward;Labarre, Maryse;Payza, Kemal;St-Onge, Stephane;Kamassah, Augustus;Morin, Pierre-Emmanuel;Projean, Denis;Ducharme, Julie;Roberts, Edward. And the article was included in Journal of Medicinal Chemistry in 2000.Electric Literature of C11H14INO This article mentions the following:

Nonpeptide δ opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews anal. of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl(1-piperazinyl)methyl]benzamide which retained potent binding affinity and selectivity to the human δ receptor (IC₅₀ = 11 nM, μ/δ = 740, κ/δ > 900) and potency as a full agonist (EC₅₀ = 36 nM) but had a markedly reduced mol. weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for δ receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for δ binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the Ph group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)methyl]benzamide which had an improved in vitro binding profile (IC₅₀ = 0.5 nM, μ/δ = 1239, EC₅₀ = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Electric Literature of C11H14INO).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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. 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.Electric Literature of C11H14INO

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

Design and synthesis of a series of truncated neplanocin fleximers was written by Zimmermann, Sarah C.;O’Neill, Elizaveta;Ebiloma, Godwin U.;Wallace, Lynsey J. M.;De Koning, Harry P.;Seley-Radtke, Katherine L.. And the article was included in Molecules in 2014.Application In Synthesis of 4,5-Diiodo-1H-imidazole This article mentions the following:

In an effort to study the effects of flexibility on enzyme recognition and activity, we have developed several different series of flexible nucleoside analogs, e.g. I (R = NH₂, Cl, OH) , in which the purine base is split into its resp. imidazole and pyrimidine components. The focus of this particular study was to synthesize the truncated neplanocin A fleximers to investigate their potential anti-protozoan activities by inhibition of S-adenosylhomocysteine hydrolase (SAHase). The three fleximers tested displayed poor anti-trypanocidal activities, with EC₅₀ values around 200 μM. Further studies of the corresponding ribose fleximers, most closely related to the natural nucleoside substrates, revealed low affinity for the known T. brucei nucleoside transporters P1 and P2, which may be the reason for the lack of trypanocidal activity observed In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Application In Synthesis of 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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. 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 4,5-Diiodo-1H-imidazole

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

N,N-Diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: A Novel, Exceptionally Selective, Potent δ Opioid Receptor Agonist with Oral Bioavailability and Its Analogues was written by Wei, Zhong-Yong;Brown, William;Takasaki, Bryan;Plobeck, Niklas;Delorme, Daniel;Zhou, Fei;Yang, Hua;Jones, Paul;Gawell, Lars;Gagnon, Helene;Schmidt, Ralf;Yue, Shi-Yi;Walpole, Chris;Payza, Kemal;St-Onge, Stephane;Labarre, Maryse;Godbout, Claude;Jakob, Andrea;Butterworth, Joanne;Kamassah, Augustus;Morin, Pierre-Emmanuel;Projean, Denis;Ducharme, Julie;Roberts, Edward. And the article was included in Journal of Medicinal Chemistry in 2000.Category: iodides-buliding-blocks This article mentions the following:

The design, synthesis, and pharmacol. evaluation of a novel class of δ opioid receptor agonists, N,N-diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide (I) and its analogs, are described. These compounds, formally derived from SNC-80 by replacing the piperazine ring with a piperidine ring containing an exocyclic carbon carbon double bond, were found to bind with high affinity and exhibit excellent selectivity for the δ opioid receptor as full agonists. I, the simplest structure in the class, exhibited an IC₅₀ = 0.87 nM for the δ opioid receptors and extremely high selectivity over the μ receptors (μ/δ = 4370) and the κ receptors (κ/δ = 8590). Rat liver microsome studies on a selected number of compounds show these olefinic piperidine compounds to be considerably more stable than SNC-80. This novel series of compounds appear to interact with δ opioid receptors in a similar way to SNC-80 since they demonstrate similar SAR. Two general approaches have been established for the synthesis of these compounds, based on dehydration of benzhydryl alcs. and Suzuki coupling reactions of vinyl bromide. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Category: iodides-buliding-blocks).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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. 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

Improved, acid-catalyzed iodinating procedures for activated aromatics with (diacetoxyiodo)benzene as the oxidant was written by Kryska, Anna;Skulski, Lech. And the article was included in Journal of Chemical Research, Synopses in 1999.HPLC of Formula: 3268-21-1 This article mentions the following:

Activated aromatics are effectively converted, at room temperature and within 15 min, into the corresponding mono-, di- or tri-iodinated products in anhydrous I₂-PhI(OAc)₂-AcOH-Ac₂O systems, acidified with catalytic amounts of concentrate H₂SO₄. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1HPLC of Formula: 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.HPLC of Formula: 3268-21-1

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

A Domino Approach (Hydrolysis/Dehydrohalogenation/Heck Coupling) for the Synthesis of Styrene Sulfonate Salts was written by Prakash, G. K. Surya;Jog, Parag V.;Krishnan, Hema S.;Olah, George A.. And the article was included in Journal of the American Chemical Society in 2011.Formula: C10H12I2 This article mentions the following:

A domino approach of hydrolysis/dehydrohalogenation/Heck coupling was used to synthesize styrene sulfonate salts from iodoarenes and chloroethanesulfonyl chloride in good to excellent yields. Methodol. was applicable for heterocyclic as well as disubstituted iodoarenes. Some of the key features of this synthetic methodol. include the use of a phosphine-free catalytic system, water as an environmentally friendly solvent, short reaction times, and absence of additives. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Formula: C10H12I2).

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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Formula: C10H12I2

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

Use of Koser’s reagent for the iodination of the rings of polyalkylbenzenes was written by Bovonsombat, Pakorn;Angara, Geetha J.;McNelis, Edward. And the article was included in Synlett in 1992.Formula: C10H12I2 This article mentions the following:

[Hydroxy(tosyloxy)iodo]benzene (Koser’s reagent) was used in catalytic quantities with N-iodosuccinimide and in stoichiometric quantities with iodine to iodinate the rings of polyalkylbenzenes (4 examples). In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Formula: C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Formula: C10H12I2

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