Tag: 200-300

Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis was written by Cho, In Seop;Gong, Leyi;Muchowski, Joseph M.. And the article was included in Journal of Organic Chemistry in 1991.Electric Literature of C12H17NO2 This article mentions the following:

A new variation of the Friedlaender quinoline synthesis was devised based on the sequential reaction of ortho-lithiated N–tert-Boc-anilines or N-pivaloylanilines with masked malondialdehyde derivatives, e.g., vinamidinium salts I (R = H, Ph), 3-(dimethylamino)acrolein, and 3-ethoxymethacrolein, and subsequent acid-induced cyclization. Thus, anilines II (R¹ = H, F, Cl, Me, OMe, R² = OCMe₃) were lithiated and cyclized with I (R = H) to give quinolines III. Lithiation of II (R¹ = F, R² = CMe₃) and cyclization with EtOCH:CMeCHO gave III (R¹ = F, R = Me). In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Electric Literature of C12H17NO2).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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 C12H17NO2

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

Synergistic Efficiency of 2-[(1-Aza-15-crown-5)-1-ylmethyl]-4-(phenyldiazenyl)-naphthalen-1-ol in the Liquid Extraction of Light Lanthanoid(III) Ions with 4-Benzoyl-3-phenyl-5-isoxazolone: The Role of Aza-Crown and Azo-Dye Fragments on the Extraction Ability was written by Petrova, Maria A.;Kurteva, Vanya B.. And the article was included in Journal of Chemical & Engineering Data in 2014.Computed Properties of C10H21NO4 This article mentions the following:

The solvent extraction of light lanthanoids with a mixture of 4-benzoyl-3-phenyl-5-isoxazolone (HPBI) and an azo-dye containing aza-crown in the side chain as a synergist (S), 2-[(1-aza-15-crown-5)-1-ylmethyl]-4-(phenyldiazenyl)-naphthalen-1-ol (PDN1A15C5), was studied. To examine the role of the azo-dye on the extraction ability, its simplified analog 1-benzyl-1-aza-15-crown-5 (BA15C5) was applied. The influence of the nitrogen on the crown fragment was estimated by a comparison with the efficiency of a series of crown ethers, benzo-15-crown-5 (B15C5) and 15-crown-5 (15C5). The lanthanoid ions were extracted from perchlorate medium at constant ionic strength 娓?= 0.1 using CHCl₃ as an organic phase. The composition of the extracted species was established as Ln(PBI)₃璺?S with PDN1A15C5 and BA15C5 and as Ln(PBI)₃璺疭 in the presence of a crown ether. The values of the equilibrium constants were calculated The influence of the synergistic agent on the extraction mechanism and enhancement is discussed. The parameters of the extraction processes were determined, and the separation factors between two adjacent lanthanoids were calculated In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Computed Properties of C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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.Computed Properties of C10H21NO4

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

Bedford-Type Palladacycle-Catalyzed Miyaura Borylation of Aryl Halides with Tetrahydroxydiboron in Water was written by Zernickel, Anna;Du, Weiyuan;Ghorpade, Seema A.;Sawant, Dinesh N.;Makki, Arwa A.;Sekar, Nagaiyan;Eppinger, Jorg. And the article was included in Journal of Organic Chemistry in 2018.Product Details of 365564-07-4 This article mentions the following:

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (HO)₂BB(OH)₂ (BBA) as a borylating agent is developed, giving arylboronates ArB(OH)₂ and ArBpin in good yields. The developed methodol. requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol%) and works best under mild reaction conditions at 40鎺?in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Product Details of 365564-07-4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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.Product Details of 365564-07-4

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

(2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as Bidentate Organoaluminum Lewis Acids: Elucidation and Synthetic Utility of the Double Electrophilic Activation Phenomenon was written by Ooi, Takashi;Takahashi, Makoto;Yamada, Masao;Tayama, Eiji;Omoto, Kiyoyuki;Maruoka, Keiji. And the article was included in Journal of the American Chemical Society in 2004.Synthetic Route of C12H17NO2 This article mentions the following:

A series of complexes I [R = Me, Me₂CH, Ph, cyclohexyl, n-octyl, 3,5-(Me₃C)₂C₆H₃] has been readily prepared in situ by treatment of the requisite 2,7-disubstituted 1,8-biphenylenediols II, readily available from inexpensive m-anisidine, with Me₃Al (2 equiv) in CH₂Cl₂ at room temperature Evaluation of complexes I as bidentate organoaluminum Lewis acids has been performed by the reduction of ketonic substrates, such as 5-nonanone and acetophenone, using Bu₃SnH as a hydride source in comparison to the conventional monodentate Lewis acid dimethylaluminum 2,6-xylenoxide, uncovering the significantly high activation ability of I toward carbonyl. Particularly, I (R = Me) exerted the highest reactivity, which has also been emphasized in the Mukaiyama aldol reaction. The structure of the bidentate Lewis acids I was unambiguously determined by single-crystal X-ray diffraction anal. of I [R = 3,5-(Me₃C)₂C₆H₃] possessing bulky di-tert-butylphenyl substituents, revealing the rigid dimeric assembly in the solid state. The double electrophilic activation of carbonyl substrate by I (R = Me) has been supported by low-temperature ¹³C NMR anal. as well as theor. study using the Gaussian 98 program. Moreover, unique stereoselectivity has been observed in the I (R = Me)-promoted Mukaiyama Michael addition, and highly chemoselective functionalization of carbonyl compounds in the presence of their acetal counterparts has been realized using I (R = Me). Finally, the effectiveness of I (R = Me) for the activation of ether functionality has been demonstrated in the Claisen rearrangement of allyl vinyl ethers. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Synthetic Route of C12H17NO2).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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.Synthetic Route of C12H17NO2

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

SiliaCat Diphenylphosphine Palladium(II) Catalyzed Borylation of Aryl Halides was written by Pandarus, Valerica;Marion, Olivier;Gingras, Genevieve;Beland, Francois;Ciriminna, Rosaria;Pagliaro, Mario. And the article was included in ChemCatChem in 2014.Name: 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Authors investigate the heterogeneously catalyzed direct synthesis of boronic acid pinacol esters using a wide range of aryl chlorides, bromides, and iodides, and bis(pinacolato)diboron as the borylating agent over the sol-gel entrapped SiliaCat diphenylphosphine palladium(II) catalyst. Optimization of the reaction conditions, scale-up of the optimized process, and anal. of palladium leaching enabled us to establish a new selective route for direct access to a diverse set of boronic acid pinacol esters. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Name: 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

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

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

Synthesis of 4-nitro- and 4-aminophenylazacrown ethers was written by Oshchepkov, Aleksandr S.;Oshchepkov, Maksim S.;Anisimov, Alexander V.;Fedorova, Olga A.. And the article was included in Makrogeterotsikly in 2015.HPLC of Formula: 66943-05-3 This article mentions the following:

The study was dedicated to finding optimal reaction conditions for the introduction of 4-nitro- and 4-aminophenyl substituents into the structure of azacrown ethers with a varied ratio of oxygen to nitrogen heteroatoms. The synthetic procedure was proposed for the synthesis of 4-nitroaryl derivatives of crown ethers. This method was remarkably simple, has easy work-up and affords the formation solely of the monoarylation product. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3HPLC of Formula: 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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. 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.HPLC of Formula: 66943-05-3

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

Silacrown ethers: synthesis of macrocyclic diphenylpolyethylene glycol mono- and disilanes was written by Oddon, Gilles;Hosseini, Mir Wais. And the article was included in Tetrahedron Letters in 1993.COA of Formula: C11H22O5 This article mentions the following:

New mono- and disilacrown ethers I–IV [[k]O_lSi_m: (k,l,m) = (8,3,1); (11,4,1); (16,6,2); (22,8,2), resp.] were prepared by reacting Ph₂SiCl₂ with HO(CH₂CH₂O)_nH (n=2, 3) in the presence of base. Variation of the bases revealed that cations could act as templates and thus orient the synthesis towards the mono- or the disilanes. In the experiment, the researchers used many compounds, for example, 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6COA of Formula: C11H22O5).

2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6) 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. 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).COA of Formula: C11H22O5

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

Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition was written by Maity, Tanmoy;Saha, Debraj;Das, Soma;Bhunia, Susmita;Koner, Subratanath. And the article was included in Catalysis Communications in 2015.Safety of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone This article mentions the following:

A highly porous Zn-based iso-reticular metal-organic framework (IRMOF-3) has been selected for covalent modification. Pyridine-2-aldehyde has been used to decorate the free amine group of IRMOF-3 in the porous matrix. Schiff base moiety thus generated has been availed to anchor copper(II) ions to prepare the desired catalyst that catalyzes O-arylation reactions heterogeneously under mild reaction conditions. Porous catalyst demonstrates size selectivity in products when various substrates undergo O-arylation with 浼?and 灏?naphthol. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Safety of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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. 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.Safety of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone

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

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature was written by Mei, Chong;Zhao, Mengdi;Lu, Wenjun. And the article was included in Journal of Organic Chemistry in 2021.Safety of N-(3-Methoxyphenyl)pivalamide This article mentions the following:

Here, in a palladium/oxidant/acid catalytic system at room temperature, one arene could highly selectively couple with the other one to afford the target unsym. biaryls just by controlling the directing groups and the substituted groups on their Ph rings was reported. The utility of this one-one cross-coupling was also demonstrated by synthesis of a few bioactive mols. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Safety of N-(3-Methoxyphenyl)pivalamide).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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).Safety of N-(3-Methoxyphenyl)pivalamide

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

Biological evaluation of pyridone alkaloids on the endocannabinoid system was written by Chicca, Andrea;Berg, Regina;Jessen, Henning J.;Marck, Nicolas;Schmid, Fabian;Burch, Patrick;Gertsch, Jurg;Gademann, Karl. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Formula: C14H15BO4 This article mentions the following:

Naturally occurring pyridone alkaloids as well as synthetic derivatives were previously shown to induce neurite outgrowth. However, the mol. basis for this biol. effect remains poorly understood. In this work, the authors have prepared new pyridones, and tested the effect of thirteen 4-hydroxy-2-pyridone derivatives on the components of the endocannabinoid system. Investigation of binding affinities towards CB₁ and CB₂ receptors led to the identification of a compound binding selectively to CB₁鑱?strong>I. Compound I and a closely related derivative also inhibited anandamide (AEA) hydrolysis by fatty acid amide hydrolase. Interestingly, none of the compounds tested showed any effect on 2-AG hydrolysis by monoacylglycerol lipase at 10 娓璏. Assessment of AEA uptake did, however, lead to the identification of four inhibitors with IC₅₀ values in the submicromolar range and high selectivity over the other components of the endocannabinoid system. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Formula: C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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 feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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: C14H15BO4

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