Month: February 2023

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water was written by Peng, Henian;Li, Tiejun;Tian, Duanshuai;Yang, He;Xu, Guangqing;Tang, Wenjun. And the article was included in Organic & Biomolecular Chemistry in 2021.HPLC of Formula: 605-94-7 This article mentions the following:

A series of unsaturated carbonyls, quinones and pyridinium salts were effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes and di- and tetrahydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient and metal-free reduction system. Deuterium-labeling experiments revealed this protocol to be an exclusive transfer hydrogenation process from water. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7HPLC of Formula: 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).HPLC of Formula: 605-94-7

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

Formation of organometallic species from complexes of N-phenylaza-crown ether conjugates with lead cations in CID-MS/MS conditions was written by Franski, Rafal;Ogorek, Katarzyna;Gierczyk, Blazej. And the article was included in International Journal of Mass Spectrometry in 2017.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Gas phase decomposition of the ions [M + PbNO₃]⁺ (M stands for fluoro-substituted N-nitrophenylaza-crown ether conjugate), has been studied by the electrospray ionization-collision induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). The conjugates containing hydrogen atom at ortho position to the crown moiety, form abundant fragment ions which can be assigned as complexes of deprotonated conjugates and lead cation, thus the ions [M – H + Pb]⁺ (fragment ions formed as a result of HNO₃ loss). Interaction between the nitro group (present at the second ortho position to the crown moiety) and the metal cation affects the formation of fragment ion [M – H + Pb]⁺ (but does not prevent its formation). Ions [M – H + Pb]⁺ are very rare example of the organometallic species (containing metal-carbon bond), in which metal cation is also complexed by crown ether moiety. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle was written by Queiroz, Maria-Joao R. P.;Calhelha, Ricardo C.;Vale-Silva, Luis A.;Pinto, Eugenia;Lima, Raquel T.;Vasconcelos, M. Helena. And the article was included in European Journal of Medicinal Chemistry in 2010.Synthetic Route of C14H21BO4 This article mentions the following:

A wide variety of new bi(hetero)aryl derivatives of the thieno[3,2-b]pyridine skeleton was obtained in high to excellent yields (65-91%) by Suzuki-Miyaura cross-coupling of the Me 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by us, with aryl or heteroaryl pinacolboranes or potassium trifluoroborates. The coupling products obtained were evaluated for their growth inhibitory effect on three human tumor cell lines, representing different tumor models, MCF-7 (breast adenocarcinoma), A375-C5 (melanoma) and NCI-H460 (non-small cell lung cancer). Some of the compounds showed an interesting activity against the tested cell lines, with GI₅₀ values in the μM range, and it was possible to establish some structure-activity relationships (SARs). Several compounds presented GI₅₀ values below 15 μM, particularly a bithiophene and an o-aniline thienopyridine derivative The first presented selectivity for MCF-7 and NCI-H460 cell lines, with very low GI₅₀ values (0.7-1.0 μM), while the latter was active against the three cell lines tested in this study, also presenting very low GI₅₀ values (2.5-4.2 μM). The effect of these two compounds on cell cycle progression was analyzed in the NCI-H460 cell line. Results showed that both compounds interfered with the normal cell cycle distribution. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Synthetic Route of C14H21BO4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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.Synthetic Route of C14H21BO4

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

Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E was written by Lloyd, Matthew G.;Taylor, Richard J. K.;Unsworth, William P.. And the article was included in Organic & Biomolecular Chemistry in 2016.Formula: C11H16O3 This article mentions the following:

Phosphorylated cyclopropanes, generated via the Rh(II)-catalyzed intramol. cyclopropanation of α-(diethoxyphosphoryl)acetates, have been found to be useful precursors in the synthesis of α-alkylidene-γ-butyrolactones. These cyclopropyl intermediates undergo regioselective reductive ring-opening and subsequent Horner-Wadsworth-Emmons olefination to complete the synthesis. Total syntheses of (±)-savinin (I) and (±)-gadain (II), as well as the first total synthesis of (±)-peperomin E (III), are all described using this method. 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. 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Formula: C11H16O3

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

Synthetic studies on indoles and related compounds. 49. Unexpected formation of quinolone derivatives in Reissert indole synthesis was written by Suzuki, Hideharu;Gyoutoku, Hiroshi;Yokoo, Hiroe;Shinba, Mika;Sato, Yuka;Yamada, Hiroshi;Murakami, Yasuoki. And the article was included in Synlett in 2000.Quality Control of 3-Methyl-4-nitroanisole This article mentions the following:

The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivatives I (R = H, 6-MeO, 5-MeO, 3-CO₂Et, 3-Me, 3-MeO, 3-Me₂CHO), sometimes in a high ratio to the expected Et indole-2-carboxylate derivatives, depending on the conditions of the catalytic reduction of the intermediate (2-nitrophenyl)pyruvates. This reactivity is characteristic in the preparation of 7-substituted indoles. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Quality Control of 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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.Quality Control of 3-Methyl-4-nitroanisole

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

Hypervalent Iodine(III)-Induced Intramolecular Cyclization of α-(Aryl)alkyl-β-dicarbonyl Compounds: A Convenient Synthesis of Benzannulated and Spirobenzannulated Compounds was written by Arisawa, Mitsuhiro;Ramesh, Namakkal G.;Nakajima, Makiko;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Journal of Organic Chemistry in 2001.Application of 3929-47-3 This article mentions the following:

A novel hypervalent iodine(III)-induced direct intramol. cyclization of α-(aryl)alkyl-β-dicarbonyl compounds has been described. Both meta- and para-substituted phenol ether derivatives containing acyclic or cyclic 1,3-dicarbonyl moieties at the side chain undergo this reaction in a facile manner. The reactions afford benzannulated and spirobenzannulated compounds that are of biol. importance. The reaction is found to be general, mild, and high yielding. The mechanism of the reaction has been shown to involve a cation radical intermediate. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application of 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. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Application of 3929-47-3

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

Microwave-assisted synthesis of 4-amino-3-[2-benzo[b]furyl]-5-mercapto-1,2,4-triazole and its derivatives was written by Wang, Xi-Cun;Quan, Zheng-Jun;Li, Zheng. And the article was included in Youji Huaxue in 2005.Electric Literature of C9H10O4 This article mentions the following:

4-Amino-3-(2-benzofuryl)-5-mercapto-1,2,4-triazole was synthesized by the reactions of 2-benzo[b]furoyl hydrazine with CS₂ and next hydrazine under microwave irradiation Treatment of the resulting 4-amino-5-mercapto-1,2,4-triazole with aromatic carboxylic acids (or aryloxyacetic acids), α-bromoacetophenones and aromatic aldehydes under microwave irradiation yielded the corresponding 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines and 4-arylideneamino-5-mercapto-1,2,4-triazole in good to moderate yields, resp. The structures of all these new compounds were confirmed by elemental analyses, IR, ¹H NMR and MS spectra. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Electric Literature of C9H10O4

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

Total Synthesis of a Noricumazole A Library and Evaluation of HCV Inhibition was written by Barbier, Jenny;Wegner, Jens;Benson, Stefan;Gentzsch, Juliane;Pietschmann, Thomas;Kirschning, Andreas. And the article was included in Chemistry – A European Journal in 2012.Computed Properties of C8H9BO4 This article mentions the following:

The total synthesis of 16 new ion channel inhibitors derived from noricumazole A I (X = O), a secondary metabolite from the myxobacterium Sorangium cellulosum, is reported. Particular focus of library design is put on stereochem. permutations in the central region (C9 and C11), the oxazole moiety and the side chain at C4 of the isochromanone moiety. Noricumazole A and all new noricumazole derivatives were tested in an assay system to determine the inhibitory effect on the hepatitis C virus (HCV) life cycle. Most of the compounds are moderate to strong HCV inhibitors (350 nM-6 nM), but also exert pronounced cytotoxicity. In contrast, the thiazole analog of noricumazole A, I (X = S), is a strong HCV inhibitor with only moderate cytotoxic property. It may become a lead structure with a good therapeutic index (CC₅₀/IC₅₀) of greater than 10. In the experiment, the researchers used many compounds, for example, 3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5Computed Properties of C8H9BO4).

3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5) 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. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Computed Properties of C8H9BO4

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

Aromatic Homologation by Non-Chelate-Assisted Rh^III-Catalyzed C-H Functionalization of Arenes with Alkynes was written by Pham, Manh V.;Cramer, Nicolai. And the article was included in Angewandte Chemie, International Edition in 2014.Electric Literature of C6H10O2 This article mentions the following:

Larger condensed arenes are of interest owing to their electro- and photochem. properties. An efficient synthesis is the catalyzed aromatic annulation of a smaller arene with two alkyne mols. Besides difunctionalized starting materials, directed C-H functionalization can be used for such aromatic homologation. However, thus far the requirement of either pre-functionalized substrates or suitable directing groups were limiting this approach. Herein, we describe a rhodium(III)-catalyzed method allowing the use of completely unbiased arenes and internal alkynes. The reaction works best with copper(II) 2-ethylhexanoate and decabromodiphenyl ether as the oxidant combination. E.g., in presence of [(Cp^*RhCl₂)₂], copper(II) 2-ethylhexanoate, and decabromodiphenyl ether, homologation of naphthalene with BuCCBu gave 60% anthracene derivative (I). This aromatic annulation tolerates a variety of functional groups and delivers homologated condensed arenes. Aside from simple benzenes, naphthalenes, and higher condensed arenes provide access to highly substituted and highly soluble acene structures having important electronic and photophys. properties. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Electric Literature of C6H10O2).

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. 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.Electric Literature of C6H10O2

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

Synthesis of 2-[(aryloxy)methyl]benzimidazole derivatives was written by Cui, Wen-hui;Zhang, You-min;Wei, Tai-bao. And the article was included in Hecheng Huaxue in 2006.Electric Literature of C9H10O4 This article mentions the following:

Twelve derivatives of 2-[(aryloxy)methyl]-1H-benzimidazole were synthesized using HCl as a catalyst and the structures were identified by ¹H NMR, IR and elemental anal. Six of the compounds are reported for the first time. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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.Electric Literature of C9H10O4

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