Month: January 2023

Palladium-Catalyzed Hydroalkylation of Alkynes with Cyclopropanols: Access to γ,δ-Unsaturated Ketones was written by Liu, Hao;Fu, Zhiyuan;Gao, Shang;Huang, Yue;Lin, Aijun;Yao, Hequan. And the article was included in Advanced Synthesis & Catalysis in 2018.Product Details of 5460-32-2 This article mentions the following:

A palladium-catalyzed hydroalkylation of alkynes with cyclopropanols has been developed. This reaction provided a straightforward way to the synthesis of γ,δ-unsaturated ketones in moderate to good yields, exhibiting high atom economy and Z/E selectivity. Deuterated tri-substituted alkenes could also be expediently produced by using deuterium oxide as a co-solvent. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Product Details of 5460-32-2).

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

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

Synthesis of hybrid acetogenins, α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines was written by Kojima, Naoto;Fushimi, Tetsuya;Maezaki, Naoyoshi;Tanaka, Tetsuaki;Yamori, Takao. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Related Products of 34091-51-5 This article mentions the following:

A series of α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogs of solamin, a natural mono-THF acetogenin, have been synthesized and their cytotoxicity was investigated against 39 tumor cell lines. One of them, 1-methylpyrazol-5-yl derivative I, showed selective increase of cytotoxicity against NCI-H23 with 80 times higher potency than solamin. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Related Products of 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) 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.Related Products of 34091-51-5

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

Antitumor benzothiazoles. 26. 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines was written by Mortimer, Catriona G.;Wells, Geoffrey;Crochard, Jean-Philippe;Stone, Erica L.;Bradshaw, Tracey D.;Stevens, Malcolm F. G.;Westwell, Andrew D.. And the article was included in Journal of Medicinal Chemistry in 2006.Category: iodides-buliding-blocks This article mentions the following:

A series of new 2-phenylbenzothiazoles has been synthesized on the basis of the discovery of the potent and selective in vitro antitumor properties of 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (I; GW 610, NSC 721648). Synthesis of analogs substituted in the benzothiazole ring was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. Compounds were evaluated in vitro in four human cancer cell lines, and I was found to possess exquisitely potent antiproliferative activity (GI₅₀ < 0.1 nM for MCF-7 and MDA 468). Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. Structure-activity relationships study established that I stands on a pinnacle of potent activity, with most structural variations having a deactivating in vitro effect. Mechanistically, this new series of agents contrasts with the previously reported 2-(4-aminophenyl)benzothiazoles; I is not reliant on induction of CYP1A1 expression for antitumor activity. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Category: iodides-buliding-blocks).

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

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

The Aryne-Abramov Reaction as a 1,2-Benzdiyne Platform for the Generation and Solvent-Dependent Trapping of 3-Phosphonyl Benzynes was written by Bembenek, Brianna M.;Petersen, Maya M. S.;Lilly, Julia A.;Haugen, Amber L.;Jiter, Naomi J.;Johnson, Andrew J.;Ripp, Ethan E.;Winchell, Shelby A.;Harvat, Alisha N.;McNulty, Caitlin;Thein, Sierra A.;Grieger, Abbigail M.;Lyle, Brandon J.;Mraz, Gabriella L.;Stitgen, Abigail M.;Foss, Samuel;Schmid, Merranda L.;Scanlon, Joseph D.;Willoughby, Patrick H.. And the article was included in Journal of Organic Chemistry in 2021.Synthetic Route of C8H7IO4 This article mentions the following:

Synthetic methodol. utilizing two aryne intermediates (i.e., a formal benzdiyne) enables the rapid generation of structurally complex mols. with diverse functionality. This report describes the sequential generation of two ortho-benzyne intermediates for the synthesis of 2,3-disubstituted aryl phosphonates. Aryl phosphonates have proven useful in medicinal chem. and materials science, and the reported methodol. provides a two-step route to functionally dense variants by way of 3-phosphonyl benzyne intermediates. The process begins with regioselective trapping of a 3-trifloxybenzyne intermediate by an O-silyl phosphite in an Abramov-like reaction to bond the strained Csp carbons with phosphorus and silicon. Standard aryne-generating conditions follow to convert the resulting 2-silylphenyl triflate into a 3-phosphonyl benzyne, which readily reacts with numerous aryne trapping reactants to form a variety of 2,3-difunctionalized aryl phosphonate products. DFT computational studies shed light on important mechanistic details and revealed that 3-phosphonyl benzynes are highly polarizable. Specifically, the distortion in the internal bond angles at each of the Csp atoms was strongly influenced by both the electronegativity of the phosphonate ester groups as well as the dielec. of the computational solvation model. These effects were verified exptl. as the regioselectivity of benzyl azide trapping increased with more electroneg. esters and/or increasingly polar solvents. Conversely, replacing the conventional solvent, acetonitrile, with nonpolar alternatives provided attenuated or even inverted selectivities. Overall, these studies showcase new reactivity of benzyne intermediates and extend the aryne relay methodol. to include organophosphonates. Furthermore, this work demonstrates that the regioselectivity of aryne trapping reactions could be tuned by simply changing the solvent. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Synthetic Route of C8H7IO4).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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.Synthetic Route of C8H7IO4

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

Synthesis of deoxypeganine and it derivatives was written by Shakhidayatov, Kh.;Irisbaev, A.;Kadyrov, Ch. Sh.. And the article was included in Khimiya Prirodnykh Soedinenii in 1974.COA of Formula: C7H6INO2 This article mentions the following:

The deoxypeganines I (R = H, Cl, Br, H2N; R1 = H) were prepared by condensation-cyclization of 4,2-R(H2N)C6H3CO2H with 2-pyrrolidinone and subsequent reduction by Zn-HCl. Similarly, 2,5-(H2N)2C6H3CO2H gave I (R = H, R1 = NH2). In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9COA of Formula: C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) 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. 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.COA of Formula: C7H6INO2

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

A general carbonyl alkylative amination for tertiary amine synthesis was written by Kumar, Roopender;Floden, Nils J.;Whitehurst, William G.;Gaunt, Matthew J.. And the article was included in Nature (London, United Kingdom) in 2020.Quality Control of 1-Bromo-4-(2-iodoethyl)benzene This article mentions the following:

The ubiquity of tertiary alkylamines in pharmaceutical and agrochem. agents, natural products and small-mol. biol. probes has stimulated efforts towards their streamlined synthesis. Arguably the most robust method for the synthesis of tertiary alkylamines is carbonyl reductive amination, which comprises two elementary steps: the condensation of a secondary alkylamine with an aliphatic aldehyde to form an all-alkyl-iminium ion, which is subsequently reduced by a hydride reagent. Direct strategies were sought for a ‘higher order’ variant of this reaction via the coupling of an alkyl fragment with an alkyl-iminium ion that was generated in situ. However, despite extensive efforts, the successful realization of a ‘carbonyl alkylative amination’ has not yet been achieved. Here the authors present a practical and general synthesis of tertiary alkylamines through the addition of alkyl radicals to all-alkyl-iminium ions. The process is facilitated by visible light and a silane reducing agent, which trigger a distinct radical initiation step to establish a chain process. This operationally straightforward, metal-free and modular transformation forms tertiary amines, without structural constraint, via the coupling of aldehydes and secondary amines with alkyl halides. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of complex tertiary amines. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Quality Control of 1-Bromo-4-(2-iodoethyl)benzene).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) 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. 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.Quality Control of 1-Bromo-4-(2-iodoethyl)benzene

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

First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis was written by Rocca, P.;Cochennec, C.;Marsais, F.;Thomas-dit-Dumont, L.;Mallet, M.;Godard, A.;Queguiner, G.. And the article was included in Journal of Organic Chemistry in 1993.Quality Control of 2-Chloro-4-iodo-3-methylpyridine This article mentions the following:

Metalation of iodopyridines was successfully achieved by LDA at low temperature In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro- and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key mols. for the preparation of fused polyaromatic alkaloids. Thus, perlolidine (I), δ-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling. Coupling of [2-(pivaloylamino)phenyl]boronic acid with 2-fluoro-4-iodo-3-pyridinecarboxaldehyde gave I. In the experiment, the researchers used many compounds, for example, 2-Chloro-4-iodo-3-methylpyridine (cas: 153034-88-9Quality Control of 2-Chloro-4-iodo-3-methylpyridine).

2-Chloro-4-iodo-3-methylpyridine (cas: 153034-88-9) 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.Quality Control of 2-Chloro-4-iodo-3-methylpyridine

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

A bright two-photon fluorescent probe for real-time monitoring autophagy in living cells was written by Jiang, Chuankun;Li, Longchun;Jiang, Jiacheng;Hou, Lilin;Fang, Gemin;Haizhu, Yu;Meng, Xiangming. And the article was included in Chinese Chemical Letters in 2020.Synthetic Route of C7H5IO2 This article mentions the following:

A novel donor-acceptor (D-A) type of two-photon (TP) fluorescent probe, i.e. Lyso-OSC, based on the lysosome-targeting morpholine group was developed. The polarity sensing coumarin group was functionalized as the acceptor and the 1-vinyl-4-methoxybenzene group was engineered as the donor. The fluorescence intensity and emission maximum wavelength of Lyso-OSC are highly sensitive to the polarity changes of solvent. The two-photon absorption cross-section and tissue penetration depth are up to 254 GM and 150μm, resp. The strong fluorescence, high sensitivity to polarity, low cytotoxicity, and accurate lysosome-targeting ability entail Lyso-OSC the excellent performance in detecting the polarity changes of cellular environment. To this end, a bright, real-time imaging autophagy of living cells has been achieved. In the experiment, the researchers used many compounds, for example, 4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2Synthetic Route of C7H5IO2).

4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2) 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. 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.Synthetic Route of C7H5IO2

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

Palladium-catalyzed alkoxycarbonylation of unactivated secondary alkyl bromides at low pressure was written by Sargent, Brendon T.;Alexanian, Erik J.. And the article was included in Journal of the American Chemical Society in 2016.Product Details of 77350-52-8 This article mentions the following:

Catalytic carbonylations of organohalides are important C-C bond formations in chem. synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Product Details of 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Product Details of 77350-52-8

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

A formal synthesis of crinipellin B based on the arene-alkane meta-photocycloaddition reaction was written by Wender, Paul A.;Dore, Timothy M.. And the article was included in Tetrahedron Letters in 1998.SDS of cas: 133232-56-1 This article mentions the following:

Starting from tri-Et phosphonopropionate and 3-nitro-2-methylbenzoic acid, a formal synthesis of crinipellin B was achieved. The strategy draws on the use of a novel version of the arene-alkene meta-photocycloaddition reaction that proceeds with the generation of 4 rings and 4 quaternary stereocenters in one synthetic operation. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1SDS of cas: 133232-56-1).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.SDS of cas: 133232-56-1

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