Category: 1993/4/9

Jacobs, Emily published the artcileExperimental and Computational Studies towards Chemoselective C-F over C-Cl Functionalisation: Reversible Oxidative Addition is the Key, COA of Formula: C11H10O, the publication is ChemCatChem (2021), 13(2), 637-645, database is CAplus.

Catalytic cross-coupling is a valuable tool for forming new carbon-carbon and carbon-heteroatom bonds, allowing access to a variety of structurally diverse compounds However, for this methodol. to reach its full potential, precise control over all competing cross-coupling sites in poly-functionalized building blocks is required. Carbon-fluorine bonds are one of the most stable bonds in organic chem., with oxidative addition at C-F being much more difficult than at other C-halide bonds. As such, the development of methods to chemoselectively functionalize the C-F position in poly-halogenated arenes would be very challenging if selectivity was to be induced at the oxidative addition step. However, metal-halide complexes exhibit different trends in reactivity to the parent haloarenes, with metal-fluoride complexes known to be very reactive towards transmetalation. In this current work, we sought to exploit the divergent reactivity of Ni-Cl and Ni-F intermediates to develop a chemoselective C-F functionalization protocol, where selectivity is controlled by the transmetalation step. Our exptl. studies highlight that such an approach is feasible, with a number of nickel catalysts shown to facilitate Hiyama cross-coupling of 1-fluoronaphthalene under base-free conditions, while no cross-coupling with 1-chloronaphthalene occurred. Computational and exptl. studies revealed the importance of reversible C-Cl oxidative addition for the development of selective C-F functionalization, with ligand effects on the potential for reversibility also presented.

ChemCatChem 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, COA of Formula: C11H10O.

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

Kasama, Kengo published the artcileChemo- and regioselective cross-dehydrogenative coupling reaction of 3-hydroxycarbazoles with arenols catalyzed by a mesoporous silica-supported oxovanadium, Category: ethers-buliding-blocks, the publication is RSC Advances (2021), 11(56), 35342-35350, database is CAplus and MEDLINE.

Cross-dehydrogenative coupling between 3-hydroxycarbazoles I(R = H; R¹ = H, Br, Me; RR¹ = -CH:CH-CH:CH-; R² = H, Me, Ph, benzyl, acetyl, tolyl) and 2-naphthols II (R³ = 6-MeO, 7-Br, 3-Me, etc.) has been achieved by using a mesoporous silica-supported oxovanadium catalyst.

RSC Advances 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

Kaye, Esther G. published the artcileA Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy, Recommanded Product: 2-Methoxynaphthalene, the publication is ACS Medicinal Chemistry Letters (2021), 12(8), 1295-1301, database is CAplus and MEDLINE.

Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.

ACS Medicinal Chemistry 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, Recommanded Product: 2-Methoxynaphthalene.

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

Zhang, Xue-wei published the artcileEcotoxicological effects of 50 kinds of fragrance materials on Microcystis aeruginosa, Category: ethers-buliding-blocks, the publication is Zhongguo Huanjing Kexue (2021), 41(3), 1429-1435, database is CAplus.

In the present study, the 50 fragrance materials were performed to determine the ecol. toxicity on Microcystis aeruginosa. The influence of four fragrance materials (2-methoxynaphthalene, thymol, myrcene and indole) on the content of chlorophyll a and soluble protein, superoxide dismutase (SOD) activity, catalase (CAT) activity and malondialdehyde (MDA) content were also studied. The results showed that 2-methoxynaphthalene, thymol, myrcene and indole can significantly inhibit the growth of Microcystis aeruginosa under high concentration exposure, and the half-effect concentration E_yC₅₀ value was 1.81, 1.26, 0.55 and 1.40 mg/L, resp., showing an obvious dose-effect relationship. At a treatment concentration of 1 mg/L, 2-methoxynaphthalene and thymol significantly inhibited the content of chlorophyll a and soluble protein (P<0.0001). Exposure to 2-methoxynaphthalene resulted in a significant decrease in SOD activity (P<0.0001), the other two antioxidant enzymes had no significant effect (P>0.05); Thymol significantly inhibited POD activity (P<0.0001), and myrcene also reduced SOD activity (P<0.01). The activities of POD and CAT of Microcystis aeruginosa treated with indole were significantly lower than those of the control group (P<0.0001). Studies showed that these four fragrance materials inhibited the antioxidant enzyme activity, accumulate excessive MDA, and destroyed the content and function of chlorophyll, which in turn leads to the abnormal growth of algae. 2-methoxynaphthalene, thymol and indole are aromatic compounds, and myrcene was an olefin. The difference in structure of the four fragrance compounds resulted to the different effects on antioxidant enzymes. 2-Methoxynaphthalene was a synthetic fragrance. Although thymol, myrcene and indole were all natural flavors, they were mostly prepared by artificial synthesis. The current findings will enrich the fundamental data for evaluating the risk and toxicity of fragrance materials on the ecosystems. Because of their unique aromatic odor, aromatic compounds have become a large category of fragrance materials and are widely used. However, the aromatic ring is stable and difficult to degrade, so we need to pay more attention to the ecol. safety of the fragrance materials with aromatic ring structure.

Zhongguo Huanjing Kexue 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 C25H34N4O2S, Category: ethers-buliding-blocks.

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

Zeng, Renping published the artcilePreparation and application of microporous carbons as excellent adsorbents for reversible iodine capture and efficient removal of dye, Category: ethers-buliding-blocks, the publication is Diamond and Related Materials (2021), 108718, database is CAplus.

Because of the application of treating hazardous wastes such as organic dyes and radioactive iodine, the porous carbon with high adsorption capacity has been a research hotspot. In this work, by the pyrolysis method with KOH activation, the hypercrosslinked polynaphthalenes were used as carbonaceous precursors to prepare porous carbons, which showed high sp. surface areas between 943.8 and 2754.5 m² g^-1 with high micropore ratios. Notably, the microporous carbonaceous materials showed an excellent iodine capture capacity of 739 wt% and a high adsorption capacity of malachite green with 1194.8 mg g^-1. These porous carbons provided potential applications in environmental remediation as promising adsorbent materials for adsorption of radioactive iodine, and removal of organic pollutants from aqueous solutions

Diamond and Related Materials 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 C16H12O, Category: ethers-buliding-blocks.

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

Wu, Zhuo published the artcilePd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated via C(sp³)-H activation, SDS of cas: 93-04-9, the publication is Chemical Science (2021), 12(24), 8531-8536, database is CAplus and MEDLINE.

Pd-catalyzed cascade cross-electrophile coupling and C-H alkylation reaction of 2-iodo-alkoxylarenes with alkyl chlorides were reported. Methoxy and benzyloxy groups, which were ubiquitous functional groups and common protecting groups, were utilized as crucial mediators via primary or secondary C(sp³)-H activation. The reaction provided an innovative and convenient access for the synthesis of alkylated phenol derivatives, which were widely found in bioactive compounds and organic functional materials.

Chemical Science 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 C8H15ClN2, SDS of cas: 93-04-9.

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

Huang, Long published the artcileBioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis, Name: 2-Methoxynaphthalene, the publication is Nature Communications (2022), 13(1), 809, database is CAplus and MEDLINE.

In the biosynthesis of sterols an enzyme-catalyzed demethylation is achieved via a stepwise oxidative transformation of alcs. e.g., 1-(4-methoxyphenyl)cyclodecan-1-ol to olefins e.g., 4-(OCH₃)C₆H₄C(O)(CH₂)₇CH=CH₂. The overall demethylation proceeds through two sequential monooxygenation reactions and a subsequent dehydroformylative saturation To mimic the desaturation processes observed in nature, photoredox proton-coupled electron transfer (PCET) and cobaloxime chem. were successfully integrated for the acceptorless dehydrogenation of alcs. The state-of-the-art remote and precise desaturation of ketones RC(O)(CH₂)₃CH=CH₂ [R = 4-(tert-butoxy)phenyl, phenanthren-9-yl, 1-benzothiophen-2-yl, etc.] proceeds efficiently through the activation of cyclic alcs. I using bond-dissociation free energy (BDFE) as thermodn. driving force. The resulting transient alkoxyl radical allows C-C bond scission to generate the carbon-centered radical remote to the carbonyl moiety. The key intermediate is subsequently combined with cobaloxime photochem. to furnish the alkene. Moreover, the mild protocol can be extended to desaturation of linear alcs. as well as aromatic hydrocarbons. Application to bioactive mols. and natural product derivatives is also presented.

Nature Communications 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, Name: 2-Methoxynaphthalene.

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

Karuppusamy, Velusamy published the artcileBF₃·OEt₂-TFAA Mediated Tetra-Functionalization of Amino Acids – Synthesis of Di- and Tri-Substituted 2-Trifluoromethyl Oxazoles in One Pot, COA of Formula: C11H10O, the publication is Organic Letters (2020), 22(18), 7147-7151, database is CAplus and MEDLINE.

A highly efficient, TFAA-BF₃·OEt₂ mediated multicomponent coupling of amino acid, TFAA, and aromatics provides a broad library of 2-trifluoromethyl equipped 2,5-disubstituted/2,4,5-trisubstituted oxazoles or N-(trifluoroacetyl)-β-aminoalkyl ketones. This amino acid tetra-functionalization approach involves amidation (C-N), anhydride (C-O), Friedel-Crafts acylation (C-C), and Robinson-Gabriel annulation (C-O) followed by dehydrative aromatization. This reaction takes place under operationally simple, mild, and metal-free conditions using readily available amino acids and aromatic compounds

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, COA of Formula: C11H10O.

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

Deng, Xiujuan published the artcileEvolution analysis of flavor-active compounds during artificial fermentation of Pu-erh tea, Formula: C11H10O, the publication is Food Chemistry (2021), 129783, database is CAplus and MEDLINE.

For the urgent need for fermentation control and product quality improvement of Pu-erh tea, gas chromatog.-mass spectrometry and odor activity value (OAV) were used to comprehensively investigate the flavor-active compounds during artificial fermentation of Pu-erh tea. A flavor wheel was constructed to expound the sensory attributes evolution during fermentation With an increased total volatiles content, 43 were significantly up-regulated and 30 were down-regulated among 131 detected volatiles. Key active compounds of three aroma types, namely fresh fragrance, fruit-fungus fragrance and stale-Qu fragrance, were analyzed based on OAV. β-damascenone was firstly found contributing most to the aroma of Pu-erh tea, followed by 1,2,3-methoxybenzene and (E,E)-2,4-nonadienal. γ-terpinene, linalool, 1,2,4-trimethoxybenzene, 1,2,3-trimethoxybenzene, and 4-ethylveratrol were identified as the potential markers responsible for aroma differences among three fermentation stages. Finally the metabolic evolution of key flavor-active compounds were systematically summarized. This study provides significant guidance in fermentation control and new product development of Pu-erh tea.

Food Chemistry 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

Gao, Han published the artcileOrigins of Lewis acid acceleration in nickel-catalyzed C-H, C-C and C-O bond cleavage, COA of Formula: C11H10O, the publication is Catalysis Science & Technology (2021), 11(13), 4417-4428, database is CAplus.

The current understanding of Lewis acid effects on transition metal catalysis is generally based on the enhanced charge transfer from metal to substrate due to the formation of Lewis acid-base adducts. The critical factors of how Lewis acids manipulate complex catalyst-substrate interactions to facilitate reactions are seldom clarified. Herein, using the energy decomposition approach, we quantify the contributions of multiple factors which account for the Lewis acid acceleration in Ni-catalyzed C-X (X = H, C, O) bond cleavage via oxidative addition The results reveal that the dominant factors for Lewis acid promotion highly depend on the features of transition states with Lewis acids. In the transition states having only heteroatom-Lewis acid interactions (e.g., C-H, C-CN and C(acyl)-O oxidative additions), the reactivity is improved majorly by enhancing charge transfer from the metal to the Lewis acid-activated substrates, which is consistent with the conventional viewpoint. However, for the transition states with heteroatom-Lewis acid and heteroatom-transition metal interactions (e.g., C(benzyl)-O and C(aryl)-O oxidative additions), the decisive factor for the improved reactivity is ascribed to the reduced Pauli repulsion between occupied orbitals. Further, in the transition states having heteroatom-Lewis acid and Lewis acid-transition metal interactions (e.g., C(benzyl)-O oxidative addition), the reaction is facilitated by strengthening electrostatics and polarization due to greater charge separation and electron delocalization effects. These three types of dominant factors are generally employed by a series of different Lewis acids in promoting Ni-catalyzed bond cleavage.

Catalysis 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, COA of Formula: C11H10O.

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