Tag: 200-300

The Coupling of Arylboronic Acids with Nitroarenes Catalyzed by Rhodium was written by Zheng, Xing-Wang;Ding, Jin-Chang;Chen, Jiu-Xi;Gao, Wen-Xiao;Liu, Miao-Chang;Wu, Hua-Yue. And the article was included in Organic Letters in 2011.SDS of cas: 54916-28-8 This article mentions the following:

The coupling of arylboronic acids with electron-deficient nitroarenes was realized for the first time by using a rhodium(I) catalyst under an air atm., achieving unsym. diaryl ethers, e.g., I with yields ranging from poor to good. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. The efficiency of this reaction was demonstrated by its compatibility with fluoro, bromo, chloro, and trifluoromethyl groups. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8SDS of cas: 54916-28-8).

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

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

Design and synthesis of Tröger’s base ditopic receptors: host-guest interactions, a combined theoretical and experimental study was written by Bhaskar Reddy, Manda;Shailaja, Myadaraboina;Manjula, Alla;Premkumar, Joseph Richard;Sastry, Garikapati Narahari;Sirisha, Katukuri;Sarma, Akella Venkata Subrahmanya. And the article was included in Organic & Biomolecular Chemistry in 2015.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Two flexible Troeger base ditopic receptors C4TB and C5TB incorporating an aza-crown ether were designed and synthesized for bis[ammonium ion] complexation. A comprehensive study of host-guest interactions was established by ¹H NMR spectroscopy and DFT calculations Bis[ammonium chloride] with a short alkyl chain spacer showed the highest affinity for the receptors. M06-2X/cc-pVTZ calculations including the solvent effects on host-guest complexes were employed to explain and rationalize the exptl. trends. The short N-H···O or N-H···N hydrogen-bond distances observed in the range of 1.71-1.98 Å indicate the existence of a strong charge assisted hydrogen bonding between the host and the guest. The unusual behavior (higher binding constant) of A5 in ¹H NMR titration is traced to the conformational folding of the guest. The synthesis of the target compounds was achieved by a reaction of 1,4,7-trioxa-10-azacyclododecane and 1,4,7,10-tetraoxa-13-azacyclopentadecane with a bis(bromoethoxy)6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine derivative (Troger’s base). In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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

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

Enhancement of transfection activity in HEK293 cells by lipoplexes containing cholesteryl nitrogen-pivoted aza-crown ethers was written by Sewbalas, Alisha;Ul Islam, Rafique;van Otterlo, Willem A. L.;de Koning, Charles B.;Singh, Moganavelli;Arbuthnot, Patrick;Ariatti, Mario. And the article was included in Medicinal Chemistry Research in 2013.Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Two nitrogen-pivoted aza-crown ethers (aza-CEs) linked to the cholesteryl-fused ring system N-(cholesteryloxycarbonyl)aza-15-crown-5 and N-(cholesteryloxycarbonyl)aza-18-crown-6 have been incorporated into cationic liposomes containing the cytofectin 3β[N-(N’,N’-dimethylaminopropane)carbamoyl] cholesterol (Chol-T) and the neutral co-lipid dioleoylphosphatidylethanolamine. These novel liposomes form stable complexes with plasmid DNA and afford it good protection from serum nuclease digestion. Ethidium displacement studies suggest that the DNA is more loosely packed in aza-CE containing lipoplexes, a finding which is supported by band shift assays that reveal N/P end point ratios of 2:1, 3:1 and 3.5:1 for Chol-T control liposomes, aza-15-crown-5 and aza-18-crown-6 containing liposomes, resp. The transfection activities of crown ether-containing lipoplex formulations in the human embryonic kidney cell line HEK293 are twofold greater than those achieved by Chol-T lipoplexes not containing the aza-CEs. This observation may be attributable to the more loosely packed DNA, which facilitates disassembly, and to endosomal perturbations caused by macrocycle entrapped cations. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Name: 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

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

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

CYP 17 and CYP 19 Inhibitors. Evaluation of Fluorine Effects on the Inhibiting Activity of Regioselectively Fluorinated 1-(Naphthalen-2-ylmethyl)imidazoles was written by Hartmann, Rolf W.;Palusczak, Anja;Lacan, Fabrice;Ricci, Giacomo;Ruzziconi, Renzo. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2004.SDS of cas: 104197-14-0 This article mentions the following:

Regioselectively fluorinated 1-(naphth-2-ylmethyl)imidazoles 1a-h have been synthesized starting from the corresponding (naphth-2-yl)methanols (2). 2a-d have been obtained by LiAlH4-promoted reduction of fluorinated 1-methyl-2-naphthaldehydes. The latter were easily prepared in fairly good overall yields by ceric ammonium nitrate (CAN)-promoted oxidative addition of the suitable 3-(fluoroaryl)-1-trimethylsilyloxy-1-butenes to Et vinyl ether in methanol followed by cyclization of the resulting acetals in strongly acidic medium in the presence of DDQ. 2e-h were prepared by LiAlH4-promoted reduction of the corresponding fluorinated Me 2-naphthoates. The latter were more profitably obtained by reacting the suitable benzyl bromide with the sodium salt of di-Me 2-(2,2-dimethoxyethyl)malonate in DMF followed by demethoxycarbonylation and acid catalyzed cyclization of the resulting acetals. Compared with the non-fluorinated parent compounds 1i-l, fluorinated 1-(naphth-2-yl)methylimidazoles 1a-h turned out to be potent inhibitors of CYP17 and CYP19 enzymes. The most active inhibitor of CYP17 is 1c, whereas CYP19 is strongly inhibited by 1b, 1e, and 1g. Interestingly, 1g is a potent dual inhibitor also being very active towards CYP19. In the experiment, the researchers used many compounds, for example, 4-Bromo-2,6-difluoroanisole (cas: 104197-14-0SDS of cas: 104197-14-0).

4-Bromo-2,6-difluoroanisole (cas: 104197-14-0) 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. 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.SDS of cas: 104197-14-0

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

A convenient synthesis of β-amino acid was written by Basheeruddin, K.;Siddiqui, Amin A.;Khan, Naseem H.;Saleha, S.. And the article was included in Synthetic Communications in 1979.Category: ethers-buliding-blocks This article mentions the following:

RCH:CHCO₂H [I; R = Ph, (Z)-CO₂H, (E)-CO₂H, Bz, 2,4-(MeO)₂C₆H₃, 2-MeOC₆H₄, 4-MeOC₆H₄, 3,4-(CH₂O₂)C₆H₃, 4,3-(MeO)(HO)C₆H₃] were treated with NH₂OH to give RCH(NHOH)CH₂CO₂H (II), which were hydrogenated over Pd/C to give the corresponding DL-RCH(NH₂)CH₂CO₂H. I (R = p-O₂NC₆H₄) was treated with NH₂OH to give II (R = p-O₂NC₆H₄), which was hydrogenated over Pd/C to give DL–p-H₂NC₆H₄CH(NH₂)CH₂CO₂H. I (R = PhCH:CH) was converted to DL-PhCH(NH₂)CH₂CH(NH₂)CO₂H by the above reactions. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Category: ethers-buliding-blocks).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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.Category: ethers-buliding-blocks

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

A new modification of the Friedlander synthesis via ortho-dilithiated N-pivaloylanilines was written by Ubeda, J. Ignacio;Villacampa, Mercedes;Avendano, Carmen. And the article was included in Synlett in 1997.Safety of N-(3-Methoxyphenyl)pivalamide This article mentions the following:

Formylation of ortho-dilithiated N-pivaloylanilines followed by treatment with carbonyl compounds and KHMDS affords 3- or 2,3-substituted quinoline derivatives in a one-pot reaction. 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. 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 N-(3-Methoxyphenyl)pivalamide

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

A rapid Hg²⁺ sensor based on aza-15-crown-5 ether functionalized 1,8-naphthalimide was written by Hou, Chen;Urbanec, Alysha M.;Cao, Haishi. And the article was included in Tetrahedron Letters in 2011.HPLC of Formula: 66943-05-3 This article mentions the following:

A new 1,8-naphthalimide derivative bearing an aza-15-crown-5 macrocycle (I) was synthesized as a chemosensor for Hg²⁺ by a two-step reaction. The sensor shows selectivity to Hg²⁺ over 11 other metal cations in aqueous media. Upon addition of Hg²⁺, the fluorescence emission of the sensor at 537 nm is significantly quenched along with 22 nm blue-shift that makes this compound a useful sensor for Hg²⁺ measurement. 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. 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.HPLC of Formula: 66943-05-3

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

Visible Light- and Heat-promoted C-O Coupling Reaction of Phenols and Aryl Halides was written by Yang, Qing-Qing;Liu, Na;Yan, Jia-Ying;Ren, Zhi-Lin;Wang, Long. And the article was included in Asian Journal of Organic Chemistry in 2020.SDS of cas: 54916-28-8 This article mentions the following:

A visible light- and heat-promoted C-O coupling reaction of phenols and aryl halides was described to afford diaryl ethers in good to excellent yields without transition-metal, photocatalysts or ligands. Moreover, the reaction had good substrate universality, suitable for substituted phenol, naphthol and heterocyclic phenol derivatives Control experiments revealed that an electron donor-acceptor (EDA) complex formed from the association of an aryl halide and phenol anion. DFT calculation further confirmed the existence of the EDA complex. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8SDS of cas: 54916-28-8).

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

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

Synthesis of 3,3-diarylpropionic acids using phosphoric acid as catalyst was written by Elsworth, J. F.;Lamchen, M.. And the article was included in Journal of the South African Chemical Institute in 1972.Recommanded Product: 3-(2,4-Dimethoxyphenyl)acrylic acid This article mentions the following:

Phenols and their Me ethers, in the presence of 85% H3PO4, readily add to the β-C atom of cinnamic acids bearing a MeO group in either the ortho or para positions on the phenyl group, to give high yields of 3,3-diarylpropionic acids. If an ortho HO group is present on the addend, the propionic acid can lactonize to yield a 4-aryldihydrocoumarin. The product from addition of 2,4-dimethoxycinnamic acid to anisole is capable reacting nucleophilically with more 2,4-dimethoxycinnamic acid to yield a bispropionic acid. A truxillic acid is obtained when 3,4-dimethoxycinnamic acid is either warmed with H3PO4 or shaken with m-xylene in the presence of H3PO4. The methoxycinnamic acid is initially protonated by H3PO4 and the derived quinonoid structure is susceptible to attack by nucleophiles. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Recommanded Product: 3-(2,4-Dimethoxyphenyl)acrylic acid).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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. 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.Recommanded Product: 3-(2,4-Dimethoxyphenyl)acrylic acid

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

Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalyzed by heteropoly salt Cs_2.5H_0.5PW₁₂O₄₀ was written by Kaur, Jaspal;Kozhevnikov, Ivan V.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2002.SDS of cas: 54916-28-8 This article mentions the following:

Heteropoly salt Cs_2.5H_0.5PW₁₂O₄₀ is a highly efficient and reusable solid acid catalyst for the liquid-phase acylation of toluene or anisole with C₂-C₁₂ aliphatic carboxylic acids. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8SDS of cas: 54916-28-8).

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

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