Month: December 2022

Yamamoto, Yuki published the artcileExcellent Catalytic Performances of a Au/C-CuO Binary System in the Selective Oxidation of Benzylamines to Imines under Atmospheric Oxygen, SDS of cas: 6850-57-3, the publication is ACS Omega (2021), 6(50), 34339-34346, database is CAplus and MEDLINE.

A green method of the oxidation of benzylamines to imines was developed using a novel binary system of Au/C-CuO. This system was evaluated under atm. oxygen, and the corresponding imines were obtained in up to 100% yields by loading 0.006 mol % of Au/C and 1.25 mol % of CuO under mild conditions. This system was also successfully applied to the syntheses of N-containing functional mols., as well as that of imines on the scale of several grams. Furthermore, the turnover number of the system (more than 8000 times on a gold basis) as well as its ability to be reused more than 10 times for benzylamine oxidation demonstrates the excellent durability and recyclability of the developed system.

ACS Omega published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C25H34N4O2S, SDS of cas: 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Calimsiz, Selcuk published the artcileNegishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent, Formula: C10H14O, the publication is Chemical Communications (Cambridge, United Kingdom) (2011), 47(18), 5181-5183, database is CAplus and MEDLINE.

Pd-PEPPSI-IPent has proven to be an excellent catalyst for the Negishi cross-coupling reaction of secondary alkylzinc reagents with a wide variety of aryl/heteroaryl halides. Importantly, β-hydride elimination/migratory insertion of the organometallic leading to the production of isomeric coupling products has been significantly reduced using the highly-hindered Ipent ligand.

Chemical Communications (Cambridge, United Kingdom) published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Formula: C10H14O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Siow, Andrew published the artcileTotal synthesis of the highly N-methylated acetylene-containing anticancer peptide Jahanyne, Related Products of ethers-buliding-blocks, the publication is Organic Letters (2018), 20(3), 788-791, database is CAplus and MEDLINE.

The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc (Fmoc = 9-fluorenylmetoxycarbonyl) solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino acids while suppressing epimerization. The total synthesis has enabled confirmation of the proposed absolute configuration of natural jahanyne.

Organic Letters published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C15H21BO3, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Goh, Jeffrey published the artcileCatalyst-free C-N bond formation under biocompatible reaction conditions, Formula: C8H11NO, the publication is Green Chemistry (2022), 24(8), 3321-3325, database is CAplus.

A C-N bond formation reaction under biocompatible conditions for the amination of allenic ketone compounds to access a diversity of β-keto enamines R¹C(O)HC=CMeNHR² [R¹ = Ph, cyclopentyl, 4-MeOC₆H₄, etc.; R² = Ph, cyclohexyl, Bn, etc.] was developed. This reaction was atom economical, green and highly regioselective and works well with many structurally important amines such as amino sugar and amino acid esters or peptides. A wide array of β-keto enamines R¹C(O)HC=CMeNHR² was obtained in modest to excellent yields with wide functional group tolerance using this protocol. A gram-scale synthesis of an anti-microbial agent was also realized using this strategy under green reaction conditions.

Green Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Formula: C8H11NO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Bankole, Paul Olusegun published the artcileNovel laccase from Xylaria polymorpha and its efficiency in the biotransformation of pharmaceuticals: Optimization of operational conditions, comparative effect of redox-mediators and toxicity studies, COA of Formula: C9H10O4, the publication is Colloids and Surfaces, B: Biointerfaces (2022), 112675, database is CAplus and MEDLINE.

The promising potentials of biocatalytic treatment processes in the removal of micropollutants while eliminating health and environmental hazards have attracted great attention in recent years. This current work investigated the biotransformation efficiency of a novel laccase from Xylaria polymorpha (XPL) in comparison with com. laccases from Trametes versicolor (TVL) and Aspergillus sp. (ASL). XPL exhibited better oxidation performance (95.7%) on AMX than TVL (92.8%) and ASL (90.5%). Optimization of operational conditions revealed that AMX was best oxidized at pH 5, temperature (30 °C), and concentration (1.0 mg L^-1). The investigation carried out to determine the effect of redox mediators revealed violuric acid (VLA) as the best redox mediator. The laccase stability experiments elucidated that the oxidation of AMX is time and mediator concentration dependent with ABTS exhibiting highest deactivation of XPL active sites. Two metabolic products; amoxicillin penilloic acid and 5-hydroxy-6-(4-hydroxyphenyl)- 3-(1,3-thiazolidin-2-yl)piperazin-2-one of AMX were obtained through Liquid Chromatog.-Mass Spectrometry (LC-MS) analyses. The toxicity assessments carried out after oxidation of AMX by XPL showed 94% and 97% reduced toxicity on Artemia salina and Aliivibrio fischeri resp. The study further underscored the efficiency of biocatalytic-mediator technol. in the transformation of complex micropollutants into less toxic substances in an eco-friendly way.

Colloids and Surfaces, B: Biointerfaces published new progress about 134-96-3. 134-96-3 belongs to ethers-buliding-blocks, auxiliary class Immunology/Inflammation,COX,Natural product, name is 4-Hydroxy-3,5-dimethoxybenzaldehyde, and the molecular formula is C9H10O4, COA of Formula: C9H10O4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Madhiri, Nicholas published the artcileOxyhalogen-sulfur chemistry: kinetics and mechanism of oxidation of formamidine disulfide by acidic bromate, Safety of Formamidine disulfide dihydrochloride, the publication is Physical Chemistry Chemical Physics (2003), 5(19), 4149-4156, database is CAplus.

The kinetics and mechanism of the oxidation of formamidine disulfide, FDS, a dimer and major metabolite of thiourea, by bromate were studied in acidic media. In excess bromate conditions the reaction displays an induction period before formation of Br. The stoichiometry of the reaction is: 7BrO₃^– + 3[H₂N(HN:)CS-]₂ + 9H₂O → 6NH₂CONH₂ + 6SO₄^2- + 7Br^– + 12H⁺ (A). In excess oxidant conditions, however, the bromide formed in reaction A reacts with bromate to give Br and a final stoichiometry of: 14BrO₃^– + 5[H₂N(HN:)CS-]₂ + 8H₂O → 10NH₂CONH₂ + 10SO₄^2- + 7Br₂ + 6H⁺ (B). The direct reaction of Br and FDS was also studied and its stoichiometry is: 7Br₂ + [H₂N(HN:)CS-]₂ + 10H₂O → 2NH₂CONH₂ + 2SO₄^2- + 14Br^– + 18H⁺ (C). The overall rate of reaction A, as measured by the rate of consumption of FDS, is second order in acid concentrations, indicating the dominance of oxyhalogen kinetics which control the formation of the reactive species HBrO₂ and HOBr. The reaction proceeds through an initial cleavage of the S-S bond to give the unstable sulfenic acids which are then rapidly oxidized through the sulfinic and sulfonic acids to give sulfate. The formation of Br coincides with formation of sulfate because the cleavage of the C-S bond to give sulfate occurs at the sulfonic acid stage only. The mechanism derived is the same as that derived for the bromate-thiourea reaction, suggesting that FDS is an intermediate in the oxidation of thiourea to its oxo-acids as well as to sulfate.

Physical Chemistry Chemical Physics published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Safety of Formamidine disulfide dihydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

de Oliveria, Lucilene L. published the artcileBis(pyrazolyl)thioether/amine-chromium(III) catalysts bearing pendant O- and N-donor group for oligomerization and polymerization of ethylene, Recommanded Product: (2-Methoxyphenyl)methanamine, the publication is Applied Organometallic Chemistry (2022), 36(4), e6609, database is CAplus.

In this work, a new family of chromium complexes supported by bis(pyrazolyl)thioether/amine ligands containing pendant O- and N-donor groups CrCl₃{S-bis[(3,5-DMPz)methyl]sulfide} (2a), CrCl₃{N-bis[(3,5-DMPz)benzylamine]} (2b), CrCl₃{N-bis[(3,5-DMPz)butylamine]} (2c), [CrCl₂{N-bis[(3,5-DMPz)methyl][(2-pyridinyl)methyl]amine}]Cl (2d), [CrCl₂{N-bis[(3,5-DMPz)methyl][quinoline]amine}]Cl (2e), [CrCl₂{N-bis[3,5-DMPz-methyl][EtNMe₂]amine}]Cl (2f), CrCl₃{N-bis[(3,5-DMPz)methyl][2-methoxyphenyl]amine} (2g), and CrCl₃{N-bis[2-(3,5-DMPz)methyl][(2-pyridyl)ethyl]amine} (2h) were synthesized and characterized by elemental anal. and Fourier transform IR spectroscopy (FTIR) spectroscopy. D. functional theory (DFT) calculations demonstrated that the pendant group as well as the spacer between the N-donor group and the central amine nitrogen have strong influence on the coordination motif of the ligand. Thus, 1d–1f act as tetradentate ligands while 1g and 1h preferably coordinated to the chromium metal center in a tridentate [N,N,N] mode fashion. The catalytic performance of 2a–2h is strongly influenced by the nature of the central bridging atom (S, N) as well as the pendant O- and N-donor group. Upon activation with methylaluminoxane (MAO), chromium precatalysts 2a–2c, 2e, and 2f generated active systems producing oligomers ranging from C₄ to C₁₂⁺ with a high selectivity for α-olefins (>82.4%). On the other hand, precatalysts bearing pyridine (2d and 2h) and methoxy (2g) functionalized amine bis (pyrazolyl) ligands exclusively produce polyethylene (PE) with activities in the range of 107.2-372.0 kg of PE·mol[Cr]^-1 h^-1.

Applied Organometallic Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Recommanded Product: (2-Methoxyphenyl)methanamine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Olah, George A. published the artcileFriedel-Crafts alkylation of anisole and its comparison with toluene. Predominant ortho-para substitution under kinetic conditions and the effect of thermodynamic isomerizations, Recommanded Product: 2-Isopropylanisole, the publication is Journal of the American Chemical Society (1984), 106(18), 5284-90, database is CAplus.

The AlCl₃-, BF₃-, and 65% HPF₆-catalyzed Friedel-Crafts alkylation of anisole with alkyl halides and alcs. was examined The alkylation of anisole with lower catalyst concentrations under mild conditions shows predominant ortho/para directing effects hdgenerally with a ratio of ∼2:1, with the amount of meta isomer <3%. With swamping catalyst conditions the amount of meta substitution in methylation and ethylation can substantially increase. The isomer distribution in tert-butylation changes with time due to rapid ortho-para interconversion. Consequently, the AlCl₃-catalyzed isomerization of isomeric alkylanisoles was also studied. In case of tert-butylanisoles, the ortho isomer shows relatively rapid conversion into para followed by much slower isomerization to meta. The para and meta isomers show isomerization to meta-para mixtures Isomerization of ethyl-, isopropyl-, and benzylanisoles is generally slow whereas methylanisoles do not isomerize. Comparing the alkylation results of anisole with those of toluene indicates that the latter are readily affected by concurrent (and in some cases consecutive) isomerization. As the barrier for isomerization in the benzenium ion intermediates of the alkylations is higher in the case of MeO- than Me-substituted systems, anisole tends to give the kinetically controlled ortho-para alkylation products and the amount of meta isomer is low. Study of alkylation of 3,5-di- and 2,4,6-trideuteriated toluene and anisole and comparing retained D contents with isomer distributions shows that alkylated product formation in the case of toluene, but not of anisole, is preceded by intramol. 1,2-alkyl, and H-D shifting, resulting also in increased meta substitution. This effect is most predominant in methylation and ethylation where the alkyl shifts are intramol. but not in tert-butylation and benzylation, where alkyl transfer is intermol. Isopropylation is intermediate in nature. No simple selectivity-reactivity relation is indicated in the alkylation reactions. As shown in benzylations with increasingly electron-donating and -withdrawing substituted benzyl chlorides, the overall rate (i.e., substrate selectivity) and isomer distributions (i.e., regioselectivity) are not determined in the same step, as significantly decreased substrate selectivity is not accompanied by loss of positional selectivity. Previously reported alkylations showing a high degree of meta substitution, therefore, must have been affected by thermodynamically controlled rearrangement processes, including intramol. alkyl and H shifts in the arenium ion intermediates of the alkylation reactions. These are to be differentiated from possible subsequent product isomerizations. Under predominantly kinetic conditions anisole as well as toluene is substantially ortho-para directing in alkylations, as in other electrophilic aromatic substitutions.

Journal of the American Chemical Society published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Recommanded Product: 2-Isopropylanisole.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Fuwa, Haruhiko published the artcileTotal Synthesis, Stereochemical Reassignment, and Biological Evaluation of (-)-Lyngbyaloside B, Computed Properties of 99438-28-5, the publication is Angewandte Chemie, International Edition (2015), 54(3), 868-873, database is CAplus and MEDLINE.

(-)-Lyngbyaloside B is a 14-membered macrolide glycoside isolated from the marine cyanobacterium Lyngbya sp. as a cytotoxic substance by Moore and co-workers. The first total synthesis of (-)-lyngbyaloside B and the reassignment of its stereo-structure is described. The synthesis features an Abiko-Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alc. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.

Angewandte Chemie, International Edition published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Computed Properties of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Noguchi, Taro published the artcileStructure-activity relationship study of neurokinin-3 receptor agonists, SDS of cas: 77128-73-5, the publication is Peptide Science (2013), 189-190, database is CAplus.

A symposium report. Neurokinin B (NKB) is a member of the tachykinin peptide family. NKB and the cognate receptor, neurokinin-3 receptor (NK3R), are involved in the secretion of the gonadotropin releasing hormone (GnRH) by kisspeptin neurons. Our SAR study demonstrated that NK3R-selectivity was improved by modifications of Phe⁵ and Val⁷ in NKB and the corresponding residues in the tachykinin peptides.

Peptide Science published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, SDS of cas: 77128-73-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem