Author: Jessica.F

Hughes, Gregory; Kreher, David; Wang, Changsheng; Batsanov, Andrei S.; Bryce, Martin R. published the artcile< Ethynyl π-extended 2,5-diphenyl-1,3,4-oxadiazoles and 2-phenyl 5-(2-thienyl)-1,3,4-oxadiazoles: synthesis, X-ray crystal structures and optical properties>, SDS of cas: 88105-22-0, the main research area is butylphenyl ethynylphenyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; heteroarylethynylphenyl oxadiazole preparation optical property; ethynylthienyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; oxadiazole phenyl ethynylthienyl preparation optical property crystal structure.

2-(4-Tert-Butylphenyl)-5-(4-ethynylphenyl)-1,3,4-oxadiazole (I, R = H) reacted with a series of heteroaryl iodides under standard Sonogashira cross-coupling conditions to yield products I [R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (II), 5-bromo-2-pyrimidyl, 2-thienyl (III) and 3-thienyl (IV)] in 40-79% yields. Compound III was lithiated followed by electrophilic iodination using perfluorohexyl iodide to give the corresponding iodothienyl derivative, which by a two-step sequence gave the terminal ethynylthienyl derivative V (R’ = H) . Conversion of V into the terminal ethynylaldehyde derivative V (R’ = CHO) via acetal derivative proceeded in high yield. Starting from 2-iodo-5-methoxycarbonylthiophene, a five-step sequence afforded 2-(4-tert-butylphenyl)-5-(4-ethynylthienyl)-1,3,4-oxadiazole (VI, R = H) (13% overall yield). Sonogashira cross-coupling reactions of VI with heteroaryl iodides gave 2-phenyl-5-(2-thienyl)-1,3,4-oxadiazoles VI (R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (VII), 5-bromo-2-pyrimidyl, 2-thienyl and 3-thienyl). Two-fold reaction of V with 2,5-diiodothiophene gave the bis(ethynylthienyl)thiophene derivative (30% yield). Solution UV-Vis absorption and photoluminescence spectra establish that replacement of the Ph ring in the 2,5-diphenyl-1,3,4-oxadiazole series I by a thienyl ring as in VI leads to a red shift in the lowest energy band in both the absorption spectra and emission spectra. The X-ray crystal structures of compounds II, IV, V and VII·CHCl3 reveal that the mol. structures are approx. planar although there are substantial differences in the conformations.

Organic & Biomolecular Chemistry published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, SDS of cas: 88105-22-0.

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

Matsumoto, Koki; Nakajima, Masaya; Nemoto, Tetsuhiro published the artcile< Determination of the best functional and basis sets for optimization of the structure of hypervalent iodines and calculation of their first and second bond dissociation enthalpies>, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole, the main research area is hypervalent iodine bond dissociation enthalpy substituent effect.

Hypervalent iodines are widely used in organic chem., and their most important feature is the three-center four-electron bond. However, there have been few reports on the measurement of their bond dissociation enthalpy (BDE). Therefore, in many cases, BDE is estimated by computational calculations However, the value of a calculated BDE usually varies depending on the choice of functional and basis set, and the best method for making an accurate evaluation of the three-center four-electron bond has not been determined We succeeded in determining the best functional and basis set to calculate the three-center four-electron bond to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis set, the first and second BDEs of several hypervalent iodines are calculated, and as the effect of benzene substituents was investigated, neg. correlation was observed in the Hammett plot. In addition, the effect of ortho-substituent in cyclic hypervalent iodine was found to be significant. Furthermore, the decomposition route of hypervalent iodine is calculated The value of a calculated BDE usually varies depending on the choice of functional and basis set. We succeeded in determining the best functional and basis sets to calculate the three-center four-electron bond of hypervalent iodine to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis sets, the first and second BDEs of several hypervalent iodines are calculated, and addnl., the decomposition route of hypervalent iodine is calculated

Journal of Physical Organic Chemistry published new progress about Bond cleavage. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole.

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

Abraham, Raymond J.; Cooper, M. Ashley published the artcile< A re-investigation of 4JFF and 5JFF nuclear spin-spin couplings in substituted benzenes, a novel conformational tool>, COA of Formula: C6H3F2I, the main research area is benzene nuclear spin coupling B3LYP.

A theor. anal. of the 4JFF and 5JFF couplings in fluorobenzenes separates the σ and π components of the substituent coefficients The π bond mechanism is dominant but the σ bond mechanism must be included to give accurate values of the couplings. For monosubstituted difluorobenzenes the 4JFF and 5JFF couplings can be predicted from the calculated π densities by linear equations. The use of additive substituent effects allows the prediction of the meta4JFF couplings for multisubstituted compounds The π dependence of the 4JFF coupling in 2,6-difluorobenzenes provides a novel and simple method of determining the torsional angle of the C1 substituent and the benzene ring for non-sym. functional groups (acetyl, carboxymethyl, dimethylamino, amide, nitro etc.). This could be used to determine the geometries of such mols. in biol. systems. The π dependence of the 4JFF coupling is also of importance in the charged species of 2,6-difluoroanilinium (4JFF 2.1 Hz) and 2,6-difluoro-N,N,N-trimethylanilinium (4JFF 0.0 Hz) due to the very different π electron densities.

Physical Chemistry Chemical Physics published new progress about Bond angle, torsional. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, COA of Formula: C6H3F2I.

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

Wang, Zhi-Xian; Duan, Weili; Wiebe, Leonard I.; Balzarini, Jan; De Clercq, Erik; Knaus, Edward E. published the artcile< Synthesis of 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-substituted-benzene thymidine mimics, some related α-anomers, and their evaluation as antiviral and anticancer agents>, Product Details of C6H3F2I, the main research area is nucleoside deoxyribofuranosyldifluorobenzene thymidine mimic synthesis antiviral cytotoxicity anticancer.

A group of unnatural 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluorobenzenes having a variety of C-5 substituents (H, Me, F, Cl, Br, I, CF3, CN, NO2, NH2), designed as thymidine mimics, were synthesized for evaluation as anticancer and antiviral agents. The coupling reaction of 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride with an organocadmium reagent [(2,4-difluorophenyl)2Cd] afforded a mixture of the α- and β-anomeric products (α:β = 3:1 to 10:1 ratio). Treatment of the α-anomer with BF3·Et2O in nitroethane at 110-120°C for 30 min was developed as an efficient method for epimerization of the major α-anomer to the desired β-anomer. The 5-substituted (H, Me, Cl, I, NH2) β-anomers exhibited negligible cytotoxicity in a MTT assay (CC50 = 10-3-10-4 M range), relative to thymidine (CC50 = 10-3-10-5 M range), against a variety of cancer cell lines. In contrast, the 5-NO2 derivative was more cytotoxic (CC50 = 10-5-10-6 M range). A number of 5-substituted β-anomers, and some related α-anomers, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV) and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive antiviral agents.

Nucleosides, Nucleotides & Nucleic Acids published new progress about Antitumor agents. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, Product Details of C6H3F2I.

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

Kervefors, Gabriella; Kersting, Leonard; Olofsson, Berit published the artcile< Transition metal-free N-arylation of amino acid esters with diaryliodonium salts>, Formula: C7H3FIN, the main research area is arylated amino acid ester synthesis transition metal free; amino acid ester arylation diaryliodonium salt hypervalent reagent; arylation reaction mechanism solvent effect protective group; amino acids; arylation; diaryliodonium salts; hypervalent compounds; transition metal-free.

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsym. diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Chemistry – A European Journal published new progress about Amino acid esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Formula: C7H3FIN.

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

Yang, Peng-Fei; Shu, Wei published the artcile< Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations>, Name: tert-Butyl (3-iodopropyl)carbamate, the main research area is amine preparation regioselective; chiral amine preparation regioselective enantioselective; alkenyl amine alkyl halide hydroalkylation metal catalyst; Amines; Chain Walking; Cobalt Catalysis; Hydroalkylations; Regiodivergent Reactions.

Herein, a catalyst-controlled synthesis of α-branched e.g., N-(1-phenylpentan-3-yl)benzamide, β-branched e.g., N-(2-methyl-4-phenylbutyl)benzamide and linear aliphatic amines e.g., N-(5-phenylpentyl)benzamide from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines e.g., N-(prop-2-en-1-yl)benzamide with alkyl halides RX (R = butan-2-yl, Bn, 2-phenylethyl, 2-(1,3-dioxolan-2-yl)ethyl, etc.; X = I, Br) is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chem. to catalytically repurpose three types of alkyl amines under mild conditions.

Angewandte Chemie, International Edition published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Name: tert-Butyl (3-iodopropyl)carbamate.

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

D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco; Mendola, Daniele; Piancatelli, Giovanni published the artcile< Photochemical behavior of halothiophenes: synthesis of 5-arylthiophene-2-carboxylic esters>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is photolysis halothiophene derivative reactivity mechanism; bithiophenecarboxylic acid propynyl; arylation photochem halothiophene derivative.

The arylation of 5-halothiophene-2-carbonitrile and Me 5-halothiophene-2-carboxylate by a photochem. process was investigated. Whereas 5-bromothiophene-2-carbonitrile is completely unreactive, the corresponding iodo derivative furnishes the dehalogenation product. In contrast, Me 5-iodothiophene-2-carboxylate gives the corresponding aryl and heteroaryl derivatives in good yields on irradiation in the presence of various aromatic substrates (benzene, p-xylene, naphthalene, thiophene, 2-bromothiophene and 2-chlorothiophene). The different reactivities of these compounds are explained. An application of this conversion to the synthesis of 5′-(1-propynyl)-2,2′-bithiophene-5-carboxylic acid is reported.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about Phosphorescence. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

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

Muthukaman, Nagarajan; Deshmukh, Sanjay; Tondlekar, Shital; Tambe, Macchindra; Pisal, Dnyandeo; Sarode, Neelam; Mhatre, Siddharth; Chakraborti, Samitabh; Shah, Daisy; Bhosale, Vikram M.; Kulkarni, Abhay; Mahat, Mahamad Yunnus A.; Jadhav, Satyawan B.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A. published the artcile< Discovery of 5-(2-chloro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-1H-tetrazole as potent and orally efficacious S-nitrosoglutathione reductase (GSNOR) inhibitors for the potential treatment of COPD>, HPLC of Formula: 887266-99-1, the main research area is imidazolyl biaryl carboxylic acid preparation nitrosoglutathione reductase inhibition SAR; biaryl imidazolyl tetrazole preparation nitrosoglutathione reductase inhibition SAR; Bioavailability; Bronchodilation; Cigarette smoke (CS); GSNOR inhibitor; Glutathione (GSH); Reductase; S-nitrosoglutathione (GSNO).

Design, synthesis and structure-activity relationships (SAR) of novel imidazole-biaryl-tetrazole I [X = C, N; R1 = H, Me, F, Cl, CF3; R2 = H, Me, Et, Cl, cyclopropyl; R3 = H, Me] based GSNOR inhibitors were described. Many potent inhibitor compounds I [X = C, R1 = Cl, R2 = R3 = H; X = C, R1 = R3 = H, R2 = Me, Et; X = C, R1 = Cl, R2 = Me, R3 = H; X = C, R1 = F, R2 = Et, R3 = H; X = N, R1 = F, R2 = Me, R3 = H] and II [X = C, R1 = H, R2 = Me] were identified with low nanomolar activity (IC50s: <15 nM) along with adequate metabolic stability. Lead compounds I [X = C, R1 = Cl, R2 = R3 = H; X = N, R1 = F, R2 = Me, R3 = H] exhibited good exposure and oral bioavailability in mouse pharmacokinetic (PK) study. Compound I [X = C, R1 = Cl, R2 = R3 = H] was selected for further profiling and revealed comparable mouse and rat GSNOR potency, high selectivity against alc. dehydrogenase (ADH) and carbonyl reductase (CBR1) family of enzymes, low efflux ratio and permeability in PAMPA, a high permeability in CALU-3 assay, significantly low hERG activity and minimal off-target activity. Further, an in-vivo efficacy of compound I [X = C, R1 = Cl, R2 = R3 = H] was disclosed in cigarette smoke (CS) induced mouse model for COPD. Bioorganic & Medicinal Chemistry Letters published new progress about Alcohol dehydrogenase inhibitors. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, HPLC of Formula: 887266-99-1.

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

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Bis(trifluoroacetoxy)iodobenzene-iodine system: an efficient and selective reagent for iodination of thiophene derivatives>, Application In Synthesis of 88105-22-0, the main research area is iodination thiophene trifluoroacetoxyiodobenzene iodide.

Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring. For example, iodination of 2-thiophenecarboxylic acid Me ester with bis(trifluoroacetoxy)iodobenzene/iodine gave 5-iodo-2-thiophenecarboxylic acid Me ester in 78% yield.

Tetrahedron Letters published new progress about Iodination, regioselective. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Application In Synthesis of 88105-22-0.

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

Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali, S. J. published the artcile< Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chloro-sugar>, Related Products of 887266-99-1, the main research area is transition state nucleophilic substitution nucleoside tetrazole preparation crystal structure; regioselective stereoselective substitution DNA nucleoside tetrazole steric effect DFT; 2,5-Disubstituted tetrazoles; Regioselective; S(N)2 reaction; Stereoselective; Tetrazolyl-N2-β-nucleosides.

We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer’s chloro-sugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chloro-sugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theor. DFT study. The methodol. is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnol. and DNA based material science applications.

Bioorganic & Medicinal Chemistry Letters published new progress about Crystal structure. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Related Products of 887266-99-1.

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