Tag: M.W=150-200

Liang, Ge published the artcileDirect C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis, SDS of cas: 93-04-9, the publication is Organic Letters (2021), 23(20), 8082-8087, database is CAplus and MEDLINE.

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies revealed that the disulfide radical cation plays a crucial role in the visible-light catalysis of aerobic thiolation. Simply controlling the equivalent ratio of substrates enables the selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction.

Organic Letters 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, SDS of cas: 93-04-9.

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

Shu, Bin published the artcileNewly generated and increased bound phenolic in lychee pulp during heat-pump drying detected by UPLC – ESI-triple-TOF-MS / MS, Safety of 4-Hydroxy-3,5-dimethoxybenzaldehyde, the publication is Journal of the Science of Food and Agriculture (2022), 102(4), 1381-1390, database is CAplus and MEDLINE.

During the thermal processing of fruit, it has been observed for phenolic compounds to either degrade, polymerize, or transfer into macromols. In this study, the bound and free phenolic compound composition, content, and phenolic-related enzyme activity of lychee pulp were investigated to determine whether the free phenolic had converted to bound phenolic during heat-pump drying (HPD). It was found that after HPD, when compared with the fresh lychee pulp (control), the content of bound phenolics of dried lychee pulp had increased by 62.69%, whereas the content of free phenolics of dried lychee pulp decreased by 22.26%. It was also found that the antioxidant activity of bound phenolics had also increased after drying. With the use of high-performance liquid chromatog.-tandem mass spectrometry, it was identified that (+)-gallocatechin, protocatechuic aldehyde, isorhamnetin-3-O-rutoside, 3,4-dihydroxybenzeneacetic acid, and 4-hydroxybenzoic acid were newly generated during HPD, when compared with the control sample. After drying, the contents of gallic acid, catechin, 4-hydroxybenzoic acid, vanillin, syringic acid, and quercetin in bound phenolics had also increased, and polyphenol oxidase and peroxidase still showed enzyme activity, which could be related to the conversion of free phenolics to bound phenolics. Overall, during the thermal processing of lychee pulp, the free phenolics weres found to be converted into bound phenolics, new substances were generated, and antioxidant activity was increased. Hence, it was concluded that HPD improved the bound phenolics content of lychee pulp, thus providing theor. support for the lychee processing industry. 2021 Society of Chem. Industry.

Journal of the Science of Food and Agriculture 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 C17H27BN2O4S, Safety of 4-Hydroxy-3,5-dimethoxybenzaldehyde.

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

Mu, Jianlou published the artcilePhenolics from sea buckthorn (Hippophae rhamnoides L.) modulate starch digestibility through physicochemical modifications brought about by starch – Phenolic molecular interactions, Category: ethers-buliding-blocks, the publication is LWT–Food Science and Technology (2022), 113682, database is CAplus.

The phenolics from sea buckthorn (SP) exert various physiol. functions. This study examined the interactions of SP on the digestive and physicochem. properties of rice (RS) and wheat starch (WS), as well as the stability of starch-phenolics during digestion. The predominant phenolics from SP were syringic acid (22.14%), gallic acid (15.23%), and catechin (11.45%). The addition of SP manipulated the rheol. of starch pastes and affected the rearrangement and multi-scale structures of starch gels. Fourier transform IR spectroscopy and X-ray diffraction revealed that SP interacted with starch mainly through non-covalent hydrogen bonds, leading to a loose starch gel structure. The content of rapidly digestible starch of RS and WS decreased by 5.66% and 7.75%; the predicted glycemic index of RS (91.65) and WS (89.34) decreased to 81.81 and 80.84, resp., when the addition level of SP reached 15%, due to the inhibition activity of SP against digestive enzymes, as well as the mol. reorganisation of starch. After the in vitro digestion, the bioaccessibility of SP in starch gels increased by a magnitude of 2.58-fold (RS) and 2.98-fold (WS). These results provide evidence of using SP as functional formulations in controlling gel-like foods structure behaviors and modulating the glycemic response of starchy foods.

LWT–Food Science and Technology 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, Category: ethers-buliding-blocks.

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

Sukowski, Verena published the artcileS,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis, SDS of cas: 2944-47-0, the publication is Angewandte Chemie, International Edition (2022), 61(31), e202201750, database is CAplus and MEDLINE.

Here, a new catalytic system based on palladium/norbornene and an S,O-ligand for the meta-C-H arylation of aryl ethers that significantly outperforms previously reported systems has been developed. The unique ability of this system to employ alkoxyarene substrates bearing electron donating and withdrawing substituents is demonstrated. Addnl., ortho-substituted aryl ethers are well tolerated, overcoming the “ortho constraint”, which is the necessity to have a meta-substituent on the alkoxyarene to achieve high reaction efficiency, by enlisting novel norbornene mediators. Remarkably, for the first time the monoarylation of alkoxyarenes is achieved efficiently enabling the subsequent introduction of a second, different aryl coupling partner to rapidly furnish unsym. terphenyls. Further insight into the reaction mechanism was achieved by isolation and characterization of some Pd-complexes-before and after meta C-H activation-prior to evaluation of their resp. catalytic activities.

Angewandte Chemie, International Edition 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 C9H20Cl2Si, SDS of cas: 2944-47-0.

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

Sumer, Zeynep published the artcileData-Centric Development of Lignin Structure-Solubility Relationships in Deep Eutectic Solvents Using Molecular Simulations, Application of 4-Hydroxy-3,5-dimethoxybenzaldehyde, the publication is ACS Sustainable Chemistry & Engineering (2022), 10(31), 10144-10156, database is CAplus.

Lignin is a natural source of aromatic chems. with significant potential as an abundant, renewable feedstock for value-added products. Deep eutectic solvents (DES)-solvents composed of a hydrogen bond donor (HBD) and acceptor (HBA) in varying ratios-have emerged as a highly tunable class of solvents for lignin solubilization. However, the variety of possible DES compositions and limited mol.-scale understanding of lignin solubility makes solvent selection a challenge without laborious trial-and-error experimentation. To address these challenges, we use classical mol. dynamics (MD) simulations to study the interactions of lignin model compounds with various DES-water systems. Quant. parameters (descriptors) were calculated by postprocessing the MD results and used to train a regression model that predicts exptl. determined solubilities of lignin model compounds This approach revealed that the most important descriptors of solubility are the system temperature, solute hydrophilicity, and metrics quantifying hydrogen bonding. Maximizing the interactions between solute-HBD (hydrophobic group), water-HBD (hydrophilic group), and water-HBA mols. led to the highest model compound solubility Our results support a hydrotropic mechanism in which extensive DES-water hydrogen bonding and favorable HBD interactions with the solute promote high solubility We applied the regression model derived using model compounds to predict the solubility of representative lignin oligomers. The model predicted lignin oligomers’ solubilities in good agreement with experiments, indicating that the simulations of model compounds can be extended to predict the solubility of larger lignin compounds across a range of solvent compositions and temperatures These findings provide new mol.-scale insight into lignin solubilization mechanisms and a new method for computationally screening potential solvent systems for lignin valorization.

ACS Sustainable Chemistry & Engineering 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 C65H82N2O18S2, Application of 4-Hydroxy-3,5-dimethoxybenzaldehyde.

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

Smit, Arjan T. published the artcileLaboratory- to Pilot-Scale Fractionation of Lignocellulosic Biomass Using an Acetone Organosolv Process, Recommanded Product: 4-Hydroxy-3,5-dimethoxybenzaldehyde, the publication is ACS Sustainable Chemistry & Engineering (2022), 10(32), 10503-10513, database is CAplus.

Acetone organosolv fractionation of beech and birch wood at laboratory-scale results in high sugar yields from the (hemi)cellulose and the isolation of a high purity lignin. In this study, the process is scaled up to validate the technol. at pilot-scale using industrial size beech and birch wood chips and low liquid-to-solid ratios as a next step toward commercialization. Translation of the fractionation process to pilot-scale showed similar performance as compared to the laboratory-scale processing with a good conversion of the wood polymeric pentoses to mostly monomeric sugars and a high delignification. Continuous lignin precipitation by solvent evaporation using the LigniSep process resulted in the formation of nonsticky lignin aggregates with a good filterability. The improved lignin yields and advanced process design as compared to the traditional dilutive lignin precipitation approaches are likely to translate to a better process economy. The pulp washing efficiency and the recovery of (nonprecipitable) lignin from the aqueous hemicellulose stream needs still to be improved for an efficient process design. However, the fractionation performance and high product concentrations in the spent liquor provide an excellent start position for improved process design at com. scale.

ACS Sustainable Chemistry & Engineering 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 C19H14Cl2, Recommanded Product: 4-Hydroxy-3,5-dimethoxybenzaldehyde.

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

Jardon, Phillip W. published the artcileMolecular orbital calculations and carbon-13 NMR studies to explain a regiospecific demethylation of 3-alkyl-1,2-dimethoxybenzenes, Name: 2-Isopropylanisole, the publication is Journal of Organic Chemistry (1984), 49(12), 2130-5, database is CAplus.

PRDDO-MO calculations show that the low-energy conformation of the carbon of a methoxy group having two ortho neighbors on a benzene ring is located out of the plane of the aromatic ring, whereas a methoxy group with only one ortho neighbor executes restricted rotation in the plane of the ring. The carbon portion of the methoxy group is turned away from the neighboring substituent. These calculations also show that the at. charge on the oxygen atom in the former case exceeds that in the latter. The carbon of a methoxy group with two ortho neighbors yields ¹³C NMR T₁ relaxation times longer than those with only one ortho neighbor, also suggesting that the methoxy group with two ortho neighbors is crowded out of the plane of the aromatic ring. ¹³C NMR chem. shifts of these ortho-substituted methoxybenzenes did not correlate well with shifts predicted from published additive parameters; this again suggests an unusual methoxy group orientation and distribution of electrons. The forced rotation of a methoxy group out of the plane of the benzene ring diminishes the release of electrons from the methoxy group to the benzene ring. The resulting higher at. charge on the oxygen and the orientation of the oxygen orbitals facilitate complexation with Lewis acids and methoxy group cleavage.

Journal of Organic Chemistry 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, Name: 2-Isopropylanisole.

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

Oguchi, Minoru published the artcileMolecular Design, Synthesis, and Hypoglycemic Activity of a Series of Thiazolidine-2,4-diones, Safety of 6-Methoxy-N2-methylpyridine-2,3-diamine, the publication is Journal of Medicinal Chemistry (2000), 43(16), 3052-3066, database is CAplus and MEDLINE.

A series of imidazopyridine thiazolidine-2,4-diones were designed and synthesized from their corresponding pyridines. These compounds represent conformationally restricted analogs of the novel hypoglycemic compound rosiglitazone. The series was evaluated for its effect on insulin-induced 3T3-L1 adipocyte differentiation in vitro and its hypoglycemic activity in the genetically diabetic KK mouse in vivo. The structure-activity relationships are discussed. On the basis of the in vivo potency, 5-[4-(5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-ylmethoxy)benzyl]thiazolidine-2,4-dione was selected as the candidate for further studies in a clin. setting.

Journal of Medicinal Chemistry published new progress about 90817-34-8. 90817-34-8 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Ether, name is 6-Methoxy-N2-methylpyridine-2,3-diamine, and the molecular formula is C7H11N3O, Safety of 6-Methoxy-N2-methylpyridine-2,3-diamine.

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

Yokoyama, Naokata published the artcileSynthesis and Structure-Activity Relationships of Oxamic Acid and Acetic Acid Derivatives Related to L-Thyronine, Quality Control of 2944-47-0, the publication is Journal of Medicinal Chemistry (1995), 38(4), 695-707, database is CAplus and MEDLINE.

Aryloxamic acids I (R = NHCOCO₂H, R¹ = Br, Me) and II, (arylamino)acetic acids I (R = NHCHRCO₂H, R¹ = Cl, Me, iodo, R² = Gly-OH, Ala-OH, Phe-OH), arylpropionic acids I (R = CH₂CH₂CO₂H, R¹ = Br, Me), arylthioacetic acids I (R = SCH₂CO₂H, R¹ = Br, Me), and (aryloxy)acetic acid I (R = OCH₂CO₂H, R¹ = Br), related to L-triiodothyronine (L-T₃) were prepared and tested in vitro for binding to the rat liver nuclear L-T₃ receptor and the rat membrane L-T₃ receptor. The structure-activity relationships for the prepared compounds are described, with several I and II showing excellent potency to the nuclear receptor and significantly lower binding affinity to the membrane receptor (IC₅₀ > 5 μM). Some of these compounds, especially in the oxamic acid series I (R = NHCOCO₂H) and II, showed an unprecedented potency for methyl-substituted derivatives such as I (R = NHCOCO₂H, R¹ = Me) and (±)-II. I (R = NHCOCO₂H, R¹ = Me) and (±)-II showed good lipid lowering effects in rats with ED₅₀ = 20 and 5 μg/kg po, resp., and a lack of cardiac side effects in rats at doses as high as 10 and 25 mg/kg po, resp.

Journal of Medicinal Chemistry 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 C6H12O2, Quality Control of 2944-47-0.

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

Bole, Leonie J. published the artcileEnhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications, Formula: C11H10O, the publication is Angewandte Chemie, International Edition (2022), 61(26), e202204262, database is CAplus and MEDLINE.

Though LiTMP (TMP = 2,2,6,6-tetramethylpiperidide) is a commonly used amide, surprisingly the heavier NaTMP has hardly been utilized. Here, by mixing NaTMP with tridentate donor PMDETA (N,N,N’,N”,N”-pentamethyldiethylenetriamine), we provide structural, and mechanistic insights into the sodiation of non-activated arenes (e.g. anisole and benzene). While these reactions are low yielding, adding B(OiPr)₃ has a profound effect, not only by intercepting the C_Ar-Na bond, but also by driving the metalation reaction towards quant. formation of more stabilized sodium aryl boronates. Demonstrating its metalating power, regioselective C2-metalation/borylation of naphthalene has been accomplished contrasting with single-metal based protocols which are unselective and low yielding. Extension to other arenes allows for in situ generation of aryl boronates which can then directly engage in Suzuki-Miyaura couplings, furnishing a range of biaryls in a selective and efficient manner.

Angewandte Chemie, International Edition 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