Category: 2689-65-8

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Name: 5-Iodo-2-furaldehyde.Wu, Qing-Feng; Shen, Peng-Xiang; He, Jian; Wang, Xiao-Bing; Zhang, Forrest; Shao, Qian; Zhu, Ru-Yi; Mapelli, Claudio; Qiao, Jennifer X.; Poss, Michael A.; Yu, Jin-Quan published the article 《Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation》 about this compound( cas:2689-65-8 ) in Science (Washington, DC, United States). Keywords: enantioselective arylation alkenylation alkynylation isobutyric acid amide organic iodide. Let’s learn more about this compound (cas:2689-65-8).

The enzymic β-C-H hydroxylation of the feedstock chem. isobutyric acid has enabled the asym. synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective β-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched α-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous iso-Pr moieties by organometallic catalysts has remained an unanswered challenge. Herein, the authors report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of iso-Pr groups via palladium insertion into the C(sp3)-H bonds of one of the prochiral Me groups. We detail the enantioselective β-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of α-chiral centers.

From this literature《Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation》,we know some information about this compound(2689-65-8)Name: 5-Iodo-2-furaldehyde, but this is not all information, there are many literatures related to this compound(2689-65-8).

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

SDS of cas: 2689-65-8. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Palladium-Catalyzed Arylation of Cyclopropanes via Directing Group-Mediated C(sp3)-H Bond Activation To Construct Quaternary Carbon Centers: Synthesis of cis- and trans-1,1,2-Trisubstituted Chiral Cyclopropanes. Author is Hoshiya, Naoyuki; Kobayashi, Takaaki; Arisawa, Mitsuhiro; Shuto, Satoshi.

Pd(II)-catalyzed tertiary C(sp3)-H arylation of cyclopropanes via directing group-mediated C-H activation for the construction of a chiral quaternary carbon center on cyclopropanes using aryl iodides as a coupling partner is reported. The arylation had a wide substrate scope and good functional group tolerance, including heteroaryl iodides, to provide various chiral arylcyclopropanes with the cis- and trans-1,1,2-trisubstituted structures.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Product Details of 2689-65-8. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Synthesis of 3-(5-R-2-furylmethylene)pentane-2,4-diones. Author is Marchalin, Stefan; Ilavsky, Dusan; Kovac, Jaroslav.

The title compounds I (R = SMe, SPh, halogen, Ph, SO2Ph, cyano, CO2Me, NO2) were obtained in 51-76% yield by reaction of the furfural derivatives with MeCOCH2COMe in the presence of CuCl2. I (R = Me, PhO, H) were prepared in the presence of β-alanine to prevent polymerization and in the absence of CuCl2.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Application In Synthesis of 5-Iodo-2-furaldehyde.Zubkov, Fedor I.; Nikitina, Eugenia V.; Galeev, Timur R.; Zaytsev, Vladimir P.; Khrustalev, Victor N.; Novikov, Roman A.; Orlova, Daria N.; Varlamov, Alexey V. published the article 《General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations》 about this compound( cas:2689-65-8 ) in Tetrahedron. Keywords: epoxyisoindole annelated synthesis tandem acylation intramol Diels Alder furan; furylazaheterocycle intramol Diels Alder annelated epoxyisoindole synthesis. Let’s learn more about this compound (cas:2689-65-8).

An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogs is presented. The method is based on tandem N-acylation/intramol. cycloaddition (the intramol. Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcs., aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Application of 2689-65-8. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Mechanism and kinetics of furfural oxidation by hydrogen peroxide. Author is Badovskaya, L. A.; Kul’nevich, V. G.; Muzychenko, G. F.; Kaklyugina, T. Ya..

The 1st-order rate constants and activation parameters for oxidation of furfural by H2O2 and the effect of 5-substituents on the rate constant indicated a heterolytic mechanism with loss of rotational and translational degrees of freedom in the transition state.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Synthetic Route of C5H3IO2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Solvent effect on rotational isomerism of furfural and its 5-substituted derivatives. Author is Rodgriguez, M.; Fernandez Bertran, J..

The solvent effect on the rotamer distribution of I (R = H) was determined from the 5Jα,4 and the 6Jα,5 in the PMR; 5Jn was inversely proportional to 6J. Polar solvents favored the cis-OO population. The substituent effect on the equilibrium was determined from the 5J for I (R = NO2, Cl, Br, I, Me2N); electron donating substituents also favored the cis-OO rotamer.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Iterative Arylation of Amino Acids and Aliphatic Amines via δ-C(sp3)-H Activation: Experimental and Computational Exploration, published in 2019, which mentions a compound: 2689-65-8, mainly applied to arylalkyl amine preparation; aliphatic amine aryl iodide arylation palladium catalyst; amino acid derivative aryl iodide arylation palladium catalyst; BODIPY labeling; arylation; density functional calculations; mechanistic studies; natural products, Reference of 5-Iodo-2-furaldehyde.

Directed C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diverse (hetero)arylation of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)-H activated intermediate has been isolated and crystallog. characterized. Mechanistic investigations carried out exptl. in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Preparation and properties of 3,5-disubstituted rhodanines, the main research direction is rhodanine benzylfurfurylidene; benzylrhodanine furfurylidene; furfurylidenerhodanine benzyl.SDS of cas: 2689-65-8.

3-Benzyl-5-furfurylidenerhodanines I (R = H, Cl, Br, I) were prepared by condensation of 3-benzylrhodanine (II) with furfural or its 5-halo derivatives in AcOH-AcONa. II was prepared by treatment of PhCH2NH2 with CS2 and KOH, condensation of the resulting PhCH2NHCS2K with ClCH2CO2K, and cyclization in the presence of concentrated HCl.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Polar properties and reactivities of some 5-substituted furfurals, the main research direction is dipole moment furfurals; furfurals dipole moment; Hammett constant furfurals; reaction rates furfurals; rates reaction furfurals.Synthetic Route of C5H3IO2.

The dipole moments (μ) were determined of the following 5-substituted furfurals (I) (substituent and μ given): Et2N, 5.66; Me2N, 5.50; piperidino, 5.43; PhNMe, 4.95; morpholino, 4.81; Me, 3.94; CHO, 3.46; H, 3.57; Br, 3.37; Cl, 3.37; I, 3.29. Linear correlations were obtained between μ and Hammett σ constant of the substituents. The relative reaction rates (k) were also determined for the reactions of I with PhNH2. A linear plot was obtained when μ were plotted vs. log k. I (R = Me, NMe2, or NEt2) have in solution primarily the cis configuration.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

SDS of cas: 2689-65-8. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent. Author is D’Auria, Maurizio; Mauriello, Giacomo.

Benzyltrimethylammonium dichloroiodate [N,N,N-trimethylbenzenemethanaminium dichloroiodate(1-)], previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group. Treatment of Me 2-thiophenecarboxylate with benzyltrimethylammonium dichloroiodate/ZnCl2/AcOH gave Me 5-iodo-2-thiophenecarboxylate, Me 4,5-diiodo-2-thiophenecarboxylate, and Me 5-chloro-2-thiophenecarboxylate.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem