Month: December 2022

D’Alfonso, Claudio published the artcileComparing the catalytic efficiency of ring substituted 1-hydroxybenzotriazoles as laccase mediators, Formula: C16H18O4, the publication is Tetrahedron (2014), 70(18), 3049-3055, database is CAplus.

A series of ring substituted 1-hydroxybenzotriazoles (6-X-HBTs) have been tested as mediators in the laccase-promoted oxidation of 4-methoxybenzyl alc., 3,4-dimethoxybenzyl alc., and the dimeric lignin model 1-(3,4-dimethoxyphenyl)-2-phenoxyethanol. The effect of the aryl substituents on the yields of oxidation products is remarkable. The catalytic mediation efficiency increases as the electron releasing (ER) properties of the substituent increases up to a maximum value for 6-CH₃-HBT, which resulted a very efficient mediator. Both the oxidation of the 6-X-HBTs to the N-oxyl radicals (6-X-BTNO) by laccase and the hydrogen atom transfer (HAT) process from the benzylic C-H to the 6-X-BTNO contribute to the overall reactivity. The former process is favored by ER substituents that lower the mediator redox potentials. On the other hand, ER substituents decrease the 6-X-BTNO reactivity in the HAT process due to a decrease in the NO-H BDE value, as assessed in this study through a radical equilibration technique.

Tetrahedron published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Formula: C16H18O4.

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

Helberger, Johann Heinrich published the artcileOrganic sulfonic acids. V. Syntheses of 1,4-butanesultone, Related Products of ethers-buliding-blocks, the publication is Justus Liebigs Annalen der Chemie (1954), 158-64, database is CAplus.

To 216 g. O.CH₂.CH₂.CH₂.CH₂ and 1.5 Zn dust was added slowly 237 g. AcCl; the mixture warmed initially at 40°, later at 60°, allowed to stand overnight, and heated 4 hrs. at 100°, giving 330 g. AcO(CH₂)₃CH₂Cl, b₁₅ 85°, 300 g. of which, refluxed 28 hrs. under N with 262 g. Na₂SO₃ in 1 l. H₂O, followed by concentration in vacuo, addition of 0.51. concentrated HCl, saturation with HCl gas, addition of MeOH, filtration, and concentration gave 280 g. HOCH₂(CH₂)₃SO₃H. Heating this acid 1.5 hrs. at 120-30°/16 mm., distilling, and removing dissolved SO₂ by N yielded 221 g. CH₂.(CH₂)₃.SO₂.O (I), b₁₃ 149-50°, large plates, m. 14.5°, nearly insoluble in cold. H₂O and CCl₄ soluble in Et₂O, CHCl₃, C₆H₆, and EtOH, hydrolyzed quantitatively to the sulfonic acid by boiling 1.5 hrs. with H₂O. [Cl(CH₂)₄]₂O (198 g.) heated and stirred under N 58 hrs. with 264 g. Na₂SO₃ in 1 l. H₂O, filtered, treated with BaCl₂, refiltered, and evaporated to dryness in vacuo gave [NaO₃SCH₂(CH₂)₃]₂O, which with saturated HCl and MeOH gave 92.3% of the corresponding free acid (II), uncrystallizable sirup. The Na salt of II, with PCl₅ and CCl₄ gave 78% acid chloride, oil, which, in Et₂O at -50° with liquid NH₃, formed [H₂NO₂S(CH₂)₄]₂O, needles, m. 104.5° (from H₂O). II (76 g.), heated 10 hrs. at 120-5°/6 mm., gave 66.8 g. I, b₅ 135-6°. As in previous publications, I gave the following hygroscopic sulfobetaines in excellent yields: (from pyridine) C₉H₁₃O₃NS, m. 249-50° (decomposition); (from PhNMe₂) C₁₂H₁₉O₃NS, m. 272-3° (decomposition); (from PhNH₂, noncrystalline glass. EtOH (15 cc.) saturated with NH₃ at 0° and heated with 1.36 g. I at 60-5° gave 1.45 g. H₂N(CH₂)₄SO₃H, m. 222-3° (decomposition) (from MeOH). The following crystalline adducts of I were also formed in 92-96% yields, by heating I with the appropriate salts or phenolates in suitable solvents: NC(CH₂)₄SO₃K, SN C(CH₂)₄SO₃K, I(CH₂)₄SO₃K, PhOCH₂(CH₂)₃SO₂Na, PhSCH₂(CH₂)₃SO₃Na, and (from K phthalimide). o-C₆H₄(CO)₂N(CH₂)₄SO₃K.

Justus Liebigs Annalen der Chemie published new progress about 183278-30-0. 183278-30-0 belongs to ethers-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain,Ether, name is Sodium 4,4′-oxybis(butane-1-sulfonate), and the molecular formula is C8H16Na2O7S2, Related Products of ethers-buliding-blocks.

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

Phelan, James P. published the artcileOpen-Air Alkylation Reactions in Photoredox-Catalyzed DNA-Encoded Library Synthesis, Formula: C25H23NO4, the publication is Journal of the American Chemical Society (2019), 141(8), 3723-3732, database is CAplus and MEDLINE.

DNA-encoded library (DEL) technol. is a powerful tool commonly used by the pharmaceutical industry for the identification of compounds with affinity to biomol. targets. Success in this endeavor lies in sampling diverse chem. libraries. However, current DELs tend to be deficient in C(sp³) carbon counts. The authors report unique solutions to the challenge of increasing both the chem. diversity of these libraries and their C(sp³) carbon counts by merging Ni/photoredox dual catalytic C(sp²)-C(sp³) cross-coupling as well as photoredox-catalyzed radical/polar crossover alkylation protocols with DELs. The successful integration of multiple classes of radical sources enables the rapid incorporation of a diverse set of alkyl fragments.

Journal of the American Chemical Society 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, Formula: C25H23NO4.

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

Ivancev-Tumbas, Ivana published the artcileAdsorption of organic pollutants from the aqueous phase using graphite as a model adsorbent, Formula: C11H10O, the publication is Adsorption Science & Technology (2020), 38(7-8), 286-303, database is CAplus.

Although graphite is not effective as an adsorbent in water treatment, it provides a homogenous, non-porous, carbonaceous structure that is ideal for studying fundamental adsorption mechanisms. High-purity graphite powder (C content 99.5%) was oxidized in an ozone stream, producing a near-surface oxygen content of 5.9 at.%, and was used together with the virgin material to establish adsorption isotherms for organic compounds in aqueous solutions We examined how the aromaticity and substituents of the adsorptives affect adsorption on the model-activated carbon surface. For both virgin and oxidized graphite, the adsorption capacity for the aromatic compounds decreased in the order 1-naphthol > 2-methoxynaphthalene > naphthalene > anisole > phenol, with significant differences in the adsorption capacities of the two graphite species observed only for anisole, naphthalene, and 1-naphthol. The Freundlich constantsfor the five compounds on virgin graphite were 23.9, 10.3, 5.5, 1.4, and 0.8 (nmol mg^-1 )/(μmol L^-1)n, resp. Naphthalene and 1-naphthol were slightly more adsorbed on the virgin material, whereas oxidized graphite had marginally better adsorption properties for anisole. The results underline the importance of dispersive and Π-Π interactions in the adsorption of organic compounds on carbonaceous adsorbents; a second aromatic ring in 1-naphthol and 2-methoxynaphthalene greatly increased the adsorption capacity for these compounds compared with their one-ring counterparts phenol and anisole. Differences were also observed in the adsorption of compounds containing hydroxyl or methoxy substituents, which have electron-donating properties (a resonance effect) but different electron-withdrawal characteristics (caused by induction). Two amino acids occurring as zwitterions, L-tryptophan and L-tyrosine, were also tested as adsorptives. L-Tryptophan, which has a larger aromatic system, achieved higher loading on graphite, suggesting an adsorption mechanism primarily governed by dispersive and Π-Π interactions for these two ionic compounds as well.

Adsorption Science & Technology published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Formula: C11H10O.

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

Stockdale, Tegan P. published the artcileA synthesis-enabled relative configurational assignment of the C31-C46 region of hemicalide, HPLC of Formula: 99438-28-5, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(38), 5729-5732, database is CAplus and MEDLINE.

Herein, through the targeted synthesis of configurationally defined fragments, as well as “encoded” mixtures of diastereomers, the stereochem. elucidation of the C31-C46 region of hemicalide I was achieved. Detailed NMR spectroscopic anal. of candidate fragments and comparison with the related hemicalide data strongly supported a 31,32-syn, 32,36-anti and 42,46-anti relationship. In combination with previous work on hemicalide, this reduced the number of possible structural permutations down to a more manageable eight diastereomers.

Chemical Communications (Cambridge, United Kingdom) 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 C15H12O6, HPLC of Formula: 99438-28-5.

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

Hamby, Taylor B. published the artcileControlling Ni redox states by dynamic ligand exchange for electroreductive C(sp³)-C(sp²) coupling, Category: ethers-buliding-blocks, the publication is Science (Washington, DC, United States) (2022), 376(6591), 410-416, database is CAplus and MEDLINE.

Cross-electrophile coupling (XEC) reactions of aryl and alkyl electrophiles are appealing but limited to specific substrate classes. Here, electroreductive XEC of previously incompatible electrophiles including tertiary alkyl bromides, aryl chlorides, and aryl/vinyl triflates are reported. The reactions rely on the merger of an electrochem. active complex that selectively reacts with alkyl bromides through 1e^– processes and an electrochem. inactive Ni⁰(phosphine) complex that selectively reacts with aryl electrophiles through 2e^– processes. Accessing Ni⁰(phosphine) intermediates is critical to the strategy but is often challenging. Here, a previously unknown pathway for electrochem. generating these key complexes at mild potentials through a choreographed series of ligand-exchange reactions has been uncovered. The mild methodol. is applied to the alkylation of a range of substrates including natural products and pharmaceuticals.

Science (Washington, DC, United States) published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Category: ethers-buliding-blocks.

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

Sunagawa, Genshun published the artcileDecomposition of benzylamine derivatives. II, SDS of cas: 52818-63-0, the publication is Yakugaku Zasshi (1952), 1570-4, database is CAplus.

cf. C.A. 46, 11210c. 2-Aminopyrimidine (I) (15 g.), 8.7 g. HCO₂H, and 18.4 g. BzH, heated 21 hrs. at 150-60°, cooled, extracted with 80 ml. dilute HCl, the aqueous layer washed with Et₂O, adjusted to pH 7-8, and the precipitate recrystallized from alc. give 18.5 g. 2-benzylaminopyrimidine (II), m. 82.5-3.5°; similarly are prepared the 2-(p-chlorobenzylamino)- (III), m. 127-8°, and 2-(p-nitrobenzylamino)pyrimidine (IV), m. 153-4°. Heating 10 g. p-MeOC₆H₄CHO, 9 g. 2-formamidopyrimidine, and 10 ml. (CH₂OH)₂ 8 hrs. at 170-80° and extracting the product as in the preparation of II gives 14.9 g. 2-(p-methoxybenzylamino)pyrimidine (V), m. 108-9°; 2-(p-MeOC₆H₄CH₂NH)C₅H₄N (VI) m. 124°; 33.2 g. PhNH₂, 10.5 g. NaHCO₃, and 10 ml. water heated with 15.7 g. p-MeOC₆H₄CH₂Cl, cooled, and the product extracted with Et₂O, washed with saturated NaCl solution, and distilled gave 16.6 g. p-MeOC₆H₄CH₂NHPh (VII), b_2.5 170-7°, m. 64-5° (from alc.); reaction of NaNH₂ and II, and treatment of the Na salt with Me₂NCH₂CH₂Cl gave p-RC₆H₄CH₂NR’R” [(VIII), R = H, R’ = 2-pyrimidyl (IX), R” = Me₂NCH₂CH₂ (X)] (XI), b₁₀ 180-4° (HCl salt, m. 204-5°); similarly, III gives VIII (R = Cl, R’ = IX, R” = X) (XII), b₃ 185-90° (HCl salt, m. 163-4°). Treating 22.5 g. anisaldoxime in 94% alc. and 170 ml. water with 60 g. Zn powder and 160 ml. 50% AcOH dropwise, heating 3 hrs. at 30-40°, cooling, alkalinizing and steam-distilling gave 20 g. p-MeOC₆H₄CH₂NH₂.HCl (XIII), m. 230-1°; heating 7.8 g. XI and 3.1 g. Me₂NCH₂CH₂Cl 1 hr. at 100°, alkalinizing, extracting with Et₂O, and distilling gave 2.2 g. (VIII, R = MeO, R’ = H, R” = X), b₁₇ 173-5° (HCl salt, m. 192-3°). Heating II, XI.HCl, and XIII, resp. with 10% HCl 5 hrs. gave unchanged raw materials; 10 g. VI yielded 0.7 g. 2-H₂NC₆H₄N (XIV), m. 57°, and 0.9 g. (p-MeOC₆H₄)₂CH₂ (XV), m. 52° (test for the presence of HCHO was pos.); 10 g. V gave 0.05 g. XV and 1.2 g. XIV; 10 g. VII gave 0.1 g. XV, HCHO, and 0.7 g. PhNH₂, b₁₀ 66° (benzoylated to 1.3 g. C₁₃H₁₁ON, m. 161°).

Yakugaku Zasshi published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C11H22N2O4, SDS of cas: 52818-63-0.

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

Ohmura, Toshimichi published the artcileIridium-Catalyzed C(sp³)-H Addition of Methyl Ethers across Intramolecular Carbon-Carbon Double Bonds Giving 2,3-Dihydrobenzofurans, Recommanded Product: 2-Isopropylanisole, the publication is Advanced Synthesis & Catalysis (2019), 361(19), 4448-4453, database is CAplus.

Intramol. addition of an O-Me C(sp³)-H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of Me 2-(propen-2-yl)phenyl ethers 2-MeC(=CH₂)-4-R-3-R¹-2-R²C₆HOMe (R = H, Me, Cl, t-Bu; R¹ = H, Me, MeO, CF₃; R² = H, Me, Ph, t-Bu, Br; R¹R² = CH=CH-CH=CH). The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110-135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans I. Enantioselective C(sp³)-H addition is achieved in the reaction of Me 2-(1-siloxyethenyl)phenyl ethers 2-TBSOC(=CH₂)-4-R³-3-R⁴-2-R⁵C₆HOMe (R³ = H, Cl, t-Bu; R⁴ = H, MeO; R⁵ = H, Me, MeO, t-Bu, Cl; R⁴R⁵ = CH=CH-CH=CH), affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives II with up to 96% ee.

Advanced Synthesis & Catalysis 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

Sekiguchi, Haruka published the artcileStructure-activity relationship study of cyclic pentapeptide ligands for atypical chemokine receptor 3 (ACKR3), Related Products of ethers-buliding-blocks, the publication is Journal of Medicinal Chemistry (2018), 61(8), 3745-3751, database is CAplus and MEDLINE.

The atypical chemokine receptor 3 (ACKR3)/CXC chemokine receptor 7 (CXCR7) recognizes stromal cell-derived factor 1 (SDF-1)/CXCL12 and is involved in a number of physiol. and pathol. processes. Here, we investigated the SAR of the component amino acids in an ACKR3-selective ligand, FC313 [cyclo(-D-Tyr-L-Arg-L-MeArg-L-Nal(2)-L-Pro-)], for the development of highly active ACKR3 ligands. Notably, modification at the L-Pro position with a bulky hydrophobic side chain led to improved bioactivity toward ACKR3.

Journal of Medicinal Chemistry 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 C22H18O2, Related Products of ethers-buliding-blocks.

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

Timofeeva, Maria N. published the artcileA layered titanosilicate AM-4 as a novel catalyst for the synthesis of 1-methoxy-2-propanole from propylene oxide and methanol, Related Products of ethers-buliding-blocks, the publication is Applied Catalysis, A: General (2019), 117240pp., database is CAplus.

In this paper we report for the first time the catalytic properties of the titanosilicate AM-4 in the synthesis of 1-methoxy-2-propanol (PGME) from methanol and propylene oxide (PO). PGME is widely used as a pollution-free solvent and intermediate in the synthesis of propylene glycol Me ether acetate, the herbicide metolachlor and in other industrial applications. We found that the catalytic properties of AM-4 could be adjusted by treatment with 0.0625-0.25 M HNO₃. Increasing the concentration of HNO₃ led to a decrease in basicity, which played a critical role in the reaction rate and the selectivity toward PGME. The yield of PGME decreased with increased acid concentration The maximum conversion of PO (88.4%) and the selectivity toward PGME (92.3%) were found to be in the presence of AM-4 at 110 °C and 8 mol/mol MeOH/PO. Our results suggest that titanosilicate AM-4 has great potential for application in basic catalysis.

Applied Catalysis, A: General published new progress about 1589-47-5. 1589-47-5 belongs to ethers-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-Methoxypropan-1-ol, and the molecular formula is C16H20N2, Related Products of ethers-buliding-blocks.

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