Tag: 100-200

Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives was written by Yang, Li;Shi, Lijun;Xing, Qi;Huang, Kuo-Wei;Xia, Chungu;Li, Fuwei. And the article was included in ACS Catalysis in 2018.COA of Formula: C8H9NO3 This article mentions the following:

The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO₂ release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd²⁺ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl₂/PPh₃/B(OH)₃ (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO₂ moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)₂/BINAP/TsOH·H₂O system (condition B), complete deoxygenation and carbonylation of the NO₂ group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodol. could be efficiently applied in the synthesis of marketed drug Aripiprazole. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8COA of Formula: C8H9NO3).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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 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.COA of Formula: C8H9NO3

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

Silver-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives was written by Fang, Zeguo;Xie, Lin;Wang, Liang;Zhang, Qian;Li, Dong. And the article was included in RSC Advances in 2022.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

The synthesis of γ-lactam-substituted quinone derivatives through a Ag₂O-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides, e.g., I was developed. Related 2-oxazolidinone substituted quinone products can be also obtained with N-aryl allyl carbamates. The reactions proceed through an amidyl radical-initiated 5-exo-trig cyclization and followed radical addition to quinones. They provide an efficient route to various γ-lactam-substituted quinone derivatives with a wide range of substrate scope. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. 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.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Thermal and Reactive Oxygen Species Dual-Responsive OEGylated Polysulfides with Oxidation-Tunable Lower Critical Solution Temperatures was written by Chen, Runhai;Xiang, Zehong;Xia, Yu;Ma, Zhifang;Shi, Qiang;Wong, Shing-Chung;Yin, Jinghua. And the article was included in Macromolecular Rapid Communications in 2020.Recommanded Product: 2-(2-Methoxyethoxy)ethanol This article mentions the following:

In this work, two monomethoxy oligo(ethylene glycol) (OEG)-substituted episulfides are prepared and a series of polysulfides are synthesized with subsequent ring-opening polymerization The OEGylated polysulfides exhibit thermal and reactive oxygen species (ROS) dual-responsive behavior. Their lower critical solution temperatures (LCSTs) are close to human body temperature and depend on the d.p. and OEG length. Notably, the LCST of the polysulfide increases linearly with the oxidation degree by H₂O₂, showing a highly tunable change regulated by the ratio between hydrophobic sulfide and hydrophilic sulfoxide/sulfone in the backbone. Further, the OEGylated polysulfide can act as a ROS scavenger to protect red blood cells (RBCs) from oxidative damage in an RBCs aging model in vitro. This work paves a facile way to synthesize LCST-tunable polysulfides, which hold great promise in biol. applications. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Recommanded Product: 2-(2-Methoxyethoxy)ethanol).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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. 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: 2-(2-Methoxyethoxy)ethanol

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

Biosynthesis of Antroquinonol and 4-Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea was written by Chou, Kevin Chi-Chung;Yang, Shang-Han;Wu, Hsiang-Lin;Lin, Pei-Yin;Chang, Tsu-Liang;Sheu, Fuu;Chen, Kai-Hsien;Chiang, Been-Huang. And the article was included in Journal of Agricultural and Food Chemistry in 2017.Recommanded Product: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

Antroquinonol (AQ) and 4-acetylantroquinonol B (4-AAQB), isolated from the submerged fermentation mycelium of Antrodia cinnamomea, have similar chem. backbone to that of coenzyme Q (CoQ). Based on the postulation that biosynthesis of both AQ and 4-AAQB in A. cinnamomea starts from polyketide pathway, the authors cultivated this fungus in a culture medium containing [U-13C]oleic acid, then analyzed the crude extracts of the mycelium using UHPLC-MS. The authors found that AQ and 4-AAQB follow the similar biosynthetic sequences as that of CoQ. Obvious [13C2] fragments on the ring backbone were detected in mass spectrum for [13C2]AQ, [13C2]4-AAQB and their [13C2] intermediates found in this study. The orsellinic acid, formed from acetyl-CoA and malonyl-CoA via polyketide pathway, was found to be a novel benzoquinone ring precursor for AQ and 4-AAQB. The identification of endogenously synthesized farnesylated intermediates allows the authors to postulate the routes of AQ and 4-AAQB biosynthesis in A. cinnamomea. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Recommanded Product: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. 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.Recommanded Product: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Synthesis and anticancer activity of nordihydroguaiaretic acid (NDGA) and analogues was written by McDonald, Russell W.;Bunjobpon, Wilawan;Liu, Tong;Fessler, Sue;Pardo, Olivier E.;Freer, Isabel K. A.;Glaser, Mark;Seckl, Michael J.;Robins, David J.. And the article was included in Anti-Cancer Drug Design in 2001.Category: ethers-buliding-blocks This article mentions the following:

Nordihydroguaiaretic acid (NDGA) is a constituent of the creosote bush Larrea divaricata and is well known to be a selective inhibitor of lipoxygenases. NDGA can also inhibit the platelet derived growth factor receptor and the protein kinase C intracellular signalling family, which both play an important role in proliferation and survival of cancers. Moreover, NDGA induces apoptosis in tumor xenografts. Although it is likely to have several targets of action, NDGA is well tolerated in animals. These encouraging results have prompted interest in the compound for clin. study. However, high concentrations of NDGA are required for efficacy and more potent analogs are required. We have synthesized five analogs of NDGA with different lengths of carbon bridge between the two catechol moieties in order to establish the spacing required for optimum anticancer effect and to compare their activities with NDGA. In order to ascertain if the catechol moieties are essential for anticancer activity, we prepared five analogs of NDGA containing only one hydroxyl group on each aromatic ring. NDGA, its racemic form, and catechol derivatives with five or six carbon atom bridges and the phenol analogs with bridges of three to six carbon atoms all showed similar activity, with IC₅₀ values of âˆ?-5 μM against the H-69 small cell lung cancer cell line. Analogs with shorter or longer bridges were much less active. The most potent analog was the biscatechol with a four-carbon bridge I which was >10 times more active than NDGA and therefore represents a new lead compound in this area. Surprisingly, the tetra-Me ether of this compound was slightly more active than NDGA, but the trihydroxy analog was less active than NDGA. In summary, simplification of the structure of NDGA by removal of the Me groups has produced a new lead compound I, which is >10 times more potent than NDGA as a proliferative inhibitor of H-69 small cell lung cancer cells. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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

Determining Factor on the Polarization Behavior of Magnesium Deposition for Magnesium Battery Anode was written by Tuerxun, Feilure;Yamamoto, Kentaro;Hattori, Masashi;Mandai, Toshihiko;Nakanishi, Koji;Choudhary, Ashu;Tateyama, Yoshitaka;Sodeyama, Keitaro;Nakao, Aiko;Uchiyama, Tomoki;Matsui, Masaki;Tsuruta, Kazuki;Tamenori, Yusuke;Kanamura, Kiyoshi;Uchimoto, Yoshiharu. And the article was included in ACS Applied Materials & Interfaces in 2020.Application of 112-49-2 This article mentions the following:

To clarify the origin of the polarization of magnesium deposition/dissolution reactions, electrochem. measurement, operando soft X-ray absorption spectroscopy (operando SXAS), Raman, and d. functional theory (DFT) techniques are combined to three different electrolytes: magnesium bis(trifluoromethanesulfonyl)amide (Mg(TFSA)₂)/triglyme, magnesium borohydride (Mg(BH₄)₂)/tetrahydrofuran (THF), and Mg(TFSA)₂/2-methyltetrahydrofuran (2-MeTHF). Cyclic voltammetry revealed that magnesium deposition/dissolution reactions occur in Mg(TFSA)₂/triglyme and Mg(BH₄)₂/THF, while the reactions do not occur in Mg(TFSA)₂/2-MeTHF. Raman spectroscopy shows that the [TFSA]^– in the Mg(TFSA)₂/triglyme electrolyte largely does not coordinate to the magnesium ions, while all of the [TFSA]^– in Mg(TFSA)₂/2-MeTHF and [BH₄]^– in Mg(BH₄)₂/THF coordinate to the magnesium ions. In operando SXAS measurements, the intermediate, such as the Mg⁺ ion, was not observed at potentials above the magnesium deposition potential, and the local structure distortion around the magnesium ions increases in all of the electrolytes at the magnesium electrode|electrolyte interface during the cathodic polarization. The DFT calculation and XPS results indicate that the [TFSA]^–, strongly bound to the magnesium ion in the Mg(TFSA)₂/2-MeTHF electrolyte, undergoes reduction decomposition easily, instead of deposition of magnesium metal, which makes the electrolyte inactive electrochem. In the Mg(BH₄)₂/THF electrolyte, because the [BH₄]^– coordinated to the magnesium ions is stable even under the potential of the magnesium deposition, the magnesium deposition is not inhibited by the decomposition of [BH₄]^–. Conversely, because [TFSA]^– is weakly bound to the magnesium ion in Mg(TFSA)₂/triglyme, the reduction decomposition occurs relatively slowly, which allows the magnesium deposition in the electrolyte. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Application of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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.Application of 112-49-2

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

Synthesis and structure of 3-isoquinolinols was written by Simchen, Gerhard;Haefner, Manfred. And the article was included in Justus Liebigs Annalen der Chemie in 1975.COA of Formula: C8H9NO3 This article mentions the following:

The isoquinolinols I (X = Cl, Br, or iodine; R = H, Cl, Br, Me, or OMe; R1 = H, Me, or OMe) were prepared by cyclization of 3,4,6-RR1(NC)C6H2CH2COCl in the presence of anhydrous HX. Hydrogenation of I over Pd/C gave I (X = H). The lactam-lactim tautomerism of these compounds was discussed. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8COA of Formula: C8H9NO3).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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.COA of Formula: C8H9NO3

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

Kinetic studies of the transesterification of dimethyl phosphite by alcohols of the guaiacyl and veratryl series was written by Vasil’eva, V. P.;Lykhina, G. G.. And the article was included in Izvestiya Tomskogo Politekhnicheskogo Instituta in 1976.Category: ethers-buliding-blocks This article mentions the following:

The reactivity of alcs. in the title reaction decreased in the order 1-guaiacyl-1-propanol > 1-veratryl-1-propanol (I) > 1-guaiacyl-3-propanol > PhCHEtOH > 1-veratryl-3-propanol (II); the rate constant for I was 15 times that for II. The absence of substituents on the Ph ring deactivated the OH group in the α-position of the propanol side chain. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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).Category: ethers-buliding-blocks

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

Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C-H Functionalization was written by Tulichala, R. N. Prasad;Shankar, Mallepalli;Swamy, K. C. Kumara. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C6H10O2 This article mentions the following:

Ruthenium-catalyzed oxidative annulation of 2H-chromene-3-carboxamides with alkynes has been achieved by using the directing group nature of amide in the presence of Cu(OAc)₂·H₂O as an oxidant and AgNTf₂ as an additive. This reaction offers a broad substrate scope, and both sym. and unsym. alkynes can be harnessed. High regioselectivity was achieved in the case of unsym. alkynes. In addition, the authors have also accomplished double C-H activation by employing an excess of alkyne, where both annulation and hydroarylation took place regio- and stereoselectively in one pot, with the catalyst playing a dual role. While the first C-H functionalization could involve Ru-N covalent bond, the second C-H functionalization most likely involves Ru-O coordinate bond. The structures of key products, e.g., I, are confirmed by x-ray crystallog. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Computed Properties of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.Computed Properties of C6H10O2

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

Synthesis of a cellulose dissolving liquid zwitterion from general and low-cost reagents was written by Sharma, Gyanendra;Kato, Yui;Hachisu, Ayumi;Ishibashi, Kojiro;Ninomiya, Kazuaki;Takahashi, Kenji;Hirata, Eishu;Kuroda, Kosuke. And the article was included in Cellulose (Dordrecht, Netherlands) in 2022.Safety of 2-(2-Methoxyethoxy)ethanol This article mentions the following:

A carboxylate-type liquid zwitterion, OE₂imC₃C, has been recently reported as a unique solvent as a class of ionic liquids with distinctive properties and functions such as cellulose dissolution ability and low toxicity to fermentative microoganisms. Therefore, OE₂imC₃C first enabled successive conversion of biomass to bioethanol in the same reaction pot. However, the reagent, 1-bromo-2-(2-methoxyethoxy)ethane, used for OE₂imC₃C synthesis is expensive and sometimes out of production and thus prevents its industrialization. Here we synthesized OE₂imC₃C from general and low-cost reagents. We also confirmed that the present OE₂imC₃C maintained the distinctive properties and functions because previous literature indicates synthetic procedures affect the properties. The low toxicity and cellulose dissolution ability of the OE₂imC₃C synthesized in this study were equivalent to those of conventional OE₂imC₃C. In addition, OE₂imC₃C is known to have ability to cryopreserve mammalian cells and the OE₂imC₃C synthesized in this study exhibited the ability. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Safety 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 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.Safety of 2-(2-Methoxyethoxy)ethanol

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