Month: February 2023

Amidines in the Diels-Alder synthesis was written by Martinez, Joaquin Royo. And the article was included in Rev. real. acad. cienc. exact. fís. y nat. Madrid in 1952.SDS of cas: 51488-33-6 This article mentions the following:

Several amidines were prepared as follows. CH₂(OH)CH₂Cl + NaCN → CH₂(OH)CH₂CN (I), b₁₅ 110° (84%); I + finely divided Al (hydroquinone to eliminate polymerization) → CH₂:CHCN (II), b. 77.6-79.0° (69.3%); II + EtOH (distilled from Na), saturated with gaseous HCl → CH₂:CHC(:NH₂Cl)OEt (III), m. 104-4.5° (decomposition), stable in bottles with airtight stoppers; III in absolute EtOH + NH₃ in absolute EtOH (3 hr. agitation, followed by standing 2 days) → CH₂:CHC(:NH₂Cl)NH₂. Similarly, vanillin + NaOH + MeI → (MeO)₂C₆H₃CHO → (MeO)₂C₆H₃CH:NOH → (MeO)₂C₆H₃CN, m. 67°, → (MeO)₂C₆H₃C(:NH₂Cl)OEt, m. 141° (decomposition) → (MeO)₂C₆H₃C(:NH₂Cl)NH₂, m. 237°. Piperonal → oxime, m. 110°, → piperonylonitrile, m. 94.5°, → Et piperonylimidate-HCl, m. 122-3°, → piperonylamidine-HCl, m. 238° (decomposition) → piperonylamidine, m. 167°, → picrate, m. 257°. PhCN → m-O₂NC₆H₄CN, m. 117.5°, → m-O₂NC₆H₄C(:NH₂Cl)OEt → m-O₂NC₆H₄(:NH₂Cl)NH₂, m. 250° (decomposition). There was no reaction comparable to a Diels-Alder, between these amidines and styrene, anethole, or maleic anhydride. MeNO₂ and CH₂(OH)CN, used as solvents, were prepared by the decarboxylation of CH₂(NO₂)CO₂H and by the addition of HCN to CH₂O, resp. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6SDS of cas: 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.SDS of cas: 51488-33-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A novel and direct synthesis of chroman derivatives using a hypervalent iodine(III) reagent was written by Hamamoto, Hiromi;Hata, Kayoko;Nambu, Hisanori;Shiozaki, Yukiko;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Tetrahedron Letters in 2004.SDS of cas: 3929-47-3 This article mentions the following:

The direct aromatic carbon-oxygen bond-formation reaction was described and the novel and simple synthetic method for chroman derivatives involving aromatic cation radical intermediates was developed using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3SDS of cas: 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.SDS of cas: 3929-47-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis of substituted 2-[bis(4-hydroxyphenyl)methyl]pyridines was written by Schulz, Otto Erich;Fedders, Soenke. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1977.Safety of (6-Methoxypyridin-2-yl)methanol This article mentions the following:

The title compounds I (R = H, R1 = 5-Me, 4-Me, 3-Me, 4-OMe, 4-Cl, 4-OCH2Ph, 4-OH, 6-OMe; R = Ac, R1 = 3-Me, 4-OMe, 4-Cl) were prepared by treating 2-methylpyridine N-oxides with Ac2O, hydrolyzing 2-acetoxymethylpyridines, oxidizing 2-hydroxymethylpyridines with SeO2, and treating 2-formylpyridines with PhOH in the presence of H2SO4. In the experiment, the researchers used many compounds, for example, (6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5Safety of (6-Methoxypyridin-2-yl)methanol).

(6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Safety of (6-Methoxypyridin-2-yl)methanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Natural Hyperbolic Dispersion with Anisotropic Epsilon-Near-Zero and Epsilon-Near-Pole in Squaraine Molecular Film was written by Kim, Minjae;Choi, Kyu Ri;Lee, Yeon Ui;Heinrich, Benoit;Ko, Soo Young;Mathevet, Fabrice;Ribierre, Jean-Charles;D′Aleo, Anthony;Wu, Jeong Weon;Placide, Virginie. And the article was included in Advanced Optical Materials in 2021.SDS of cas: 111-77-3 This article mentions the following:

Epsilon-near-zero (ENZ) optical material has been employed in a number of novel linear and nonlinear optical applications, owing to the vanishing polarization upon an incident optical wave. In a uniaxial medium possessing hyperbolic energy-momentum dispersion of optical wave, ENZ can take place at ordinary and extraordinary permittivities. Organic thin films presenting a lamellar structure have been reported to exhibit a transverse neg. hyperbolic dispersion with ENZ at ordinary permittivity. Here, organic thin film with ENZ at extraordinary permittivity is demonstrated. Newly synthesized polymethine dye (i.e., squaraine indolenine triethyleneglycol mol.) self-organizes to form a layered structure in a pristine film, and both transverse neg. and pos. hyperbolic dispersions are observed at visible wavelengths. Anal. of tens-nanometer-thick pristine film shows that both ENZ and epsilon-near-pole (ENP) occur at longitudinal as well as transverse component of dielec. permittivity. Optical characterization of squaraine pristine film is presented, and the importance of transverse pos. hyperbolic dispersion in such monolithic thin film is discussed. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3SDS of cas: 111-77-3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.SDS of cas: 111-77-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Naturally occurring compounds related to phenalenone. Part 9. Synthesis of 8,9-dihydro-1,2,3,6-tetrahydroxy-4,8,8,9-tetramethylphenaleno[1,2-b]furan-7-one and 8,9-dihydro-1,4,5,6-tetrahydroxy-3,8,8,9-tetramethylphenaleno[1,2-b]furan-7-one was written by Halton, David D.;Morrison, George A.. And the article was included in Journal of Chemical Research, Synopses in 1979.Category: ethers-buliding-blocks This article mentions the following:

The title furanones (I; R = H, R¹ = Me, R² = R³ = OH; R = R¹ = OH, R² = Me, R³ = H, resp.) were prepared in 9 steps from 3,4,5-(MeO)₃C₆H₂CH₂CHO (II), for which an improved synthesis was developed. The key intermediate in the syntheses was the naphthalene III, obtained in 9.4% overall yield. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Category: ethers-buliding-blocks).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Identification of Acyl Protein Thioesterases 1 and 2 as the Cellular Targets of the Ras-Signaling Modulators Palmostatin B and M was written by Rusch, Marion;Zimmermann, Tobias J.;Buerger, Marco;Dekker, Frank J.;Goermer, Kristina;Triola, Gemma;Brockmeyer, Andreas;Janning, Petra;Boettcher, Thomas;Sieber, Stephan A.;Vetter, Ingrid R.;Hedberg, Christian;Waldmann, Herbert. And the article was included in Angewandte Chemie, International Edition in 2011.Formula: C11H16O3 This article mentions the following:

Activity-based proteomic profiling probes based on the depalmitoylation inhibitors palmostatin B and M have been synthesized and were found to target acyl protein thioesterase 1 (APT1) and 2 (APT2) in cells. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Formula: C11H16O3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Formula: C11H16O3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Anti-angiogenic properties of coenzyme Q₀ through downregulation of MMP-9/NF-κB and upregulation of HO-1 signaling in TNF-α-activated human endothelial cells was written by Yang, Hsin-Ling;Korivi, Mallikarjuna;Lin, Ming-Wei;Chen, Ssu-Ching;Chou, Chih-Wei;Hseu, You-Cheng. And the article was included in Biochemical Pharmacology (Amsterdam, Netherlands) in 2015.SDS of cas: 605-94-7 This article mentions the following:

Various coenzyme Q (CoQ) analogs have been reported as anti-inflammatory and antioxidant substances. However, coenzyme Q₀ (CoQ₀, 2,3-dimethoxy-5-methyl-1,4-benzoquinone), a novel quinone derivative, has not been well studied for its pharmacol. efficacies, and its response to cytokine stimulation remains unclear. Therefore, the authors investigated the potential anti-angiogenic properties of CoQ₀ in human endothelial (EA.hy 926) cells against tumor necrosis factor-α (TNF-α) stimulation. The authors found that the non-cytotoxic concentrations of CoQ₀ (2.5-10 μM) significantly suppressed the TNF-α-induced migration/invasion and tube formation abilities of endothelial cells. CoQ₀ suppressed TNF-α-induced activity and protein expressions of matrix metalloproteinase-9 (MMP-9) and intercellular adhesion mol.-1 (ICAM-1) followed by an abridged adhesion of U937 leukocytes to endothelial cells. CoQ₀ treatment remarkably downregulated TNF-α-induced nuclear translocation and transcriptional activation of nuclear factor-κB (NF-κB) possibly through suppressed I-κBα degradation Furthermore, CoQ₀ triggered the expressions of heme oxygenase-1 (HO-1) and γ-glutamylcysteine synthetase (γ-GCLC), followed by an increased nuclear accumulation of NF-E2 related factor-2 (Nrf2)/antioxidant response element (ARE) activity. In agreement with these, intracellular glutathione levels were significantly increased in CoQ₀ treated cells. More interestingly, knockdown of HO-1 gene by specific shRNA showed diminished anti-angiogenic effects of CoQ₀ against TNF-α-induced invasion, tube formation and adhesion of leukocyte to endothelial cells. The authors’ findings reveal that CoQ₀ protective effects against cytokine-stimulation are mediated through the suppression of MMP-9/NF-κB and/or activation of HO-1 signaling cascades. This novel finding emphasizes the pharmacol. efficacies of CoQ₀ to treat inflammation and angiogenesis. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7SDS of cas: 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.SDS of cas: 605-94-7

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Semi-Reduction of Internal Alkynes with Prototypical Subnanometric Metal Surfaces: Bridging Homogeneous and Heterogeneous Catalysis with Trinuclear All-Metal Aromatics was written by Monfredini, Anna;Santacroce, Veronica;Marchio, Luciano;Maggi, Raimondo;Bigi, Franca;Maestri, Giovanni;Malacria, Max. And the article was included in ACS Sustainable Chemistry & Engineering in 2017.Name: 1,4-Dimethoxy-2-butyne This article mentions the following:

Suitably delocalized metal-metal bonds can stabilize a particular class of discrete trinuclear complexes that are the transition-metal counterparts of carbon-based aromatics This chem. stability has pivoted the development of an advantageous catalytic method for the semiredn. of internal alkynes under transfer hydrogenation condition. The reaction does not require any addnl. solvent and a simple workup delivers pure products. This combines with broad functional group tolerance, complete cis-selectivity and catalytic charges down to 100 ppm on multigram scale. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Name: 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Name: 1,4-Dimethoxy-2-butyne

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation. Preparation of α,β-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands was written by Rossi, D.;Urbano, M.;Baraglia, A. Carnevale;Serra, M.;Bergamelli, F.;Iannelli, M.;Azzolina, O.;Collina, S.. And the article was included in Synthetic Communications in 2009.Recommanded Product: 6972-61-8 This article mentions the following:

The optimal conditions to prepare α,β-unsaturated Me esters via Wittig reaction combining polymer-assisted solution-phase synthesis (PASPS) methodol. and simultaneous ultrasound and microwave irradiation were established. The effects of temperature, solvent, and irradiation time were discussed. Results clearly indicated the superiority of combined ultrasound and microwave-assisted procedure over microwave-assisted methodol. Moreover, an efficient PASPS procedure to prepare α,β-unsaturated carboxylic acids via tandem Wittig olefination and hydrolysis reaction was developed under combined ultrasound and microwave irradiation Generally, a good conversion of aldehydes to acids was observed The optimized protocols allowed us to quickly prepare a small collection of either α,β-unsaturated esters or carboxylic acids, key intermediates for the drug-discovery process of new sigma ligands. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Recommanded Product: 6972-61-8).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Recommanded Product: 6972-61-8

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The difluoromethylthio moiety lowers the LCST of oligo(ethylene glycol)-based homopolymers was written by Liu, Haoyu;Ding, Aishun;Ma, Chen;Huang, Xiaoyu;Feng, Chun;Wang, Zhiqin;Wang, Zhaolei;Lu, Guolin. And the article was included in Polymer Chemistry in 2020.Application In Synthesis of 2-(2-Methoxyethoxy)ethanol This article mentions the following:

A series of thermo-responsive homopolymers bearing difluoromethylthio and oligo(ethylene glycol) moieties in each repeat unit were firstly synthesized from newly synthesized acrylamide monomers, N-3-(difluoromethylthio)propyl-N-(3-methoxyl-(ethoxy)n-3-oxopropyl)acrylamide, i.e., DFTP-MEO_n-AM (n = 2-5). These new DFTP-MEO_n-AM monomers were prepared from a key amine intermediate bearing difluoromethylthio through aza-Michael addition reaction followed by amidation with acryloyl chloride. Well-defined poly(DFTP-MEO_n-AM) homopolymers obtained via reversible addition-fragmentation chain transfer (RAFT) polymerization exhibited good temperature-responsive properties. The LCSTs of poly(DFTP-MEO_n-AM) homopolymers are ~35°C lower than those of corresponding poly(Bu-MEO_n-AM) homopolymers without fluorine, which demonstrated that introduction of difluoromethylthio moiety could effectively lower LCST of related polymers. LCSTs of poly(DFTP-MEO₄-AM) homopolymers were also affected by isotopic solvent, polymer concentration, salt, urea, etc. Temperature-variable ¹H NMR anal. indicated that difluoromethylthio moiety could affect the dehydration process of poly(DFTP-MEO₄-AM) homopolymer above LCST. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Application In Synthesis of 2-(2-Methoxyethoxy)ethanol).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application In Synthesis of 2-(2-Methoxyethoxy)ethanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem