Category: ethers-buliding-blocks

Panda, Atulya Kumar published the artcile< A facile synthesis of di-O-methylcentrolobol>, Name: 4-(4-Methoxyphenyl)-1-butanol, the main research area is centrolobol methyl ether preparation; phenylbutyl bromide benzenepropanal Grignard.

A facile route to (±)-di-O-methylcentrolobol was explored starting from 4-oxo-4-(4-methoxyphenyl)butanoic acid and 4-methoxycinnamic acid.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 52244-70-9. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Name: 4-(4-Methoxyphenyl)-1-butanol.

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

Adimurthy, Subbarayappa; Patoliya, Paresh U. published the artcile< N-Bromosuccinimide. A facile reagent for the oxidation of benzylic alcohols to aldehydes>, Quality Control of 17100-64-0, the main research area is benzylic alc oxidation bromosuccinimide reagent; aldehyde aromatic preparation; benzyl bromide preparation.

The oxidation of benzylic alcs. to aldehydes using N-bromosuccinimide (NBS) under ambient conditions without use of a transition-metal catalyst was described.

Synthetic Communications published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 17100-64-0 belongs to class ethers-buliding-blocks, and the molecular formula is C8H9BrO2, Quality Control of 17100-64-0.

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

Kidwai, Mazaahir; Batra, Rajini published the artcile< A new route to thiaziridine 1,1-dioxides>, Reference of 10305-42-7, the main research area is thiaziridine dioxide alkyl; sulfamoyl chloride cyclocondensation diazomethane; alkylthiaziridine dioxide.

Title compounds I (R = CMe3, Me, Pr, CHMe2, CH2CHMe2) were prepared by reacting ClSO2NHR with RCHN2 in ether and NEt3.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about Cyclocondensation reaction. 10305-42-7 belongs to class ethers-buliding-blocks, and the molecular formula is C3H8ClNO2S, Reference of 10305-42-7.

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

Heck, Richard; Winstein, S. published the artcile< Neighboring carbon and hydrogen. XXVII. Ar1-5 aryl participation and tetralin formation in solvolysis>, Related Products of 52244-70-9, the main research area is .

p-MeOC6H4CH:CHCO2H added by means of a Soxhlet apparatus to 1.5 mole equivalents LiAlH4 yielded 44% p-MeOC6H4(CH2)3OH. 2,4-(MeO)2C6H3CH:CHCO2H (46 g.) reduced similarly with 12 g. LiAlH4 during 2 days gave 39% 2,4-(MeO)2C6H3(CH2)3OH, b3.5, 144-5°, nD25 1.5320, m. 36-8°. Ph(CH2)3CO2H reduced with LiAlH4 yielded Ph(CH2)4OH (I). I heated 1 hr. on the steam bath with Ac2O and a few drops pyridine gave the acetate (II), b8.5 120 °, nD25 1.4948. p-MeOC6H4(CH2)3CO2H reduced with LiAlH4 yielded 91.5% p-MeOC6H4(CH2)4OH (III), b1.5 125-30°, nD25 1.5200. 2,4-(MeO)2C6H3(CH2)3CO2H (IV) gave similarly 100% 2,4-(MeO)2C6H3(CH2)4OH (V), b2.5 157-61°, nD25 1.5296; p-nitrobenzoate (VI), m. 52-3° (from MeOH). Ph(CH2)3MgCl and ethylene oxide gave Ph(CH2)5OH, b3 110-13°, nD25 1.5149. The various primary alcs. were converted to the corresponding p-bromobenzenesulfonates (m.p. given) by the method described previously (Bs is used throughout this abstract to designate the group p-BrC6H4SO2): Ph(CH2)3OBs (VII), 35.5-7.5°; p-MeOC6H4(CH2)3OBs (VIII), 62-4°; 2,4-(MeO)2C6H3(CH2)3OBs (IX), 56-7°; Ph(CH2)4OBs (X), 21-3.5° (nD25 1.5694); p-MeOC6H4(CH2)4OBs (XI), 43-5°; 2,4-(MeO)2C6H3(CH2)4OBs (XII), 54.5-6.5°; Ph(CH2)5OBs (XIII), 34-5.5°. Glutaric anhydride (40 g.) and 50 g. m-C6H4(OMe)2 in 450 cc. purified tetrachloroethane treated at 0° with stirring with 100 g. anhydrous AlCl3 in small portions, the mixture kept about 0.5 hr. at 0°, treated with ice and dilute HCl, and worked up in the usual manner, and the product recrystallized from aqueous MeOH yielded 18 g. 2,4-(MeO)2C6H3CO(CH2)3CO2H (XIV), m. 106-7°. XIV (17 g.) refluxed 2 days with 50 g. Hg-Zn, 30 cc. PhMe, 30 cc. H2O, and 70 cc. concentrated HCl while 10 cc. concentrated HCl was added every 6 hrs., the PhMe phase extracted with aqueous NaHCO3, and the aqueous extract acidified gave 5.5 g. 2,4-(MeO)2C6H3(CH2)4CO2H (XV), m. 97-8.5° (from aqueous MeOH). XV reduced with LiAlH4 gave 96% 2,4-(MeO)2C6H3(CH2)5OH, b2 144-5°, nD25 1.5247; it gave with p-BrC6H4SO2Cl 90%-pure p-bromobenzenesulfonate (XVa). Ph(CH2)3CH(OH)Me (XVI) (15 g.), b1 80-4°, nD25 1.5108, in 75 cc. dry pyridine treated with 25 g. p-MeC6H4SO2Cl below room temperature, kept 2 hrs. at room temperature, and the product isolated with Et2O gave an oil which chromatographed on Al2O3 and eluted with C6H6-pentane yielded 9.5 g. p-toluenesulfonate (XVII) of XVI, nD25 1.5382. IV (16 g.) in 50 cc. Et2O added dropwise with stirring to MeLi from 25 g. MeI and 2.5 g. Li in 200 cc. Et2O, the mixture stirred 0.5 hr. and treated with cold dilute HCl, the Et2O layer worked up, and the product, b2 120-50°, reduced with LiAlH4 yielded 3.5 g. 2,4-(MeO)2C6H3(CH2)3CH(OH)Me b2 135-9°, nD25 1.5219, which gave a 70%-pure p-toluenesulfonate (XVIII), nD25 1.5250. The rates of the acetolysis in AcOH were determined by the method described previously (C.A. 51, 2830d) for the following compounds (temperature, M × 102 concentration of ester, and k in sec.-1 given): VII, 75.00°, 3.18, (1.07 ± 0.00)10-6; VII, 100.05°, 2.71, (1.17 ± 0.01)10-5; VIII, 75.00°, 3.04, (1.15 ± 0.03)10-6; IX, 75.00°, 2.57, 3.95 × 10-6; X, 75.00°, 3.09, (1.45 ± 0.03)10-6; X, 75.00°, 3.02, (1.49 ± 0.05)10-6; X, 100.05°, 3.68, (1.62 ± 0.01)10-5; XI, 75.00°, 2.66, (1.90 ± 0.01)10-6; XI, 100.05°, 2.16, (2.16 ± 0.01)10-5; XII, 75.00°, 2.66, (6.26 ± 0.06)10-6; XII, 100.00°, 1.94, (7.56 ± 0.05)10-5; XII (AcOH 0.0300M in LiClO4), 75.00°, 2.89, (7.2 ± 0.1)10-6; XIII, 75.00°, 2.77, (1.54 ± 0.03)10-6; XIII, 100.00°, 2.64, (1.65 ± 0.01)10-5; XVa, 75.00°, 2.40, (1.61 ± 0.03)10-6; XVa, 100.10°, 2.40, (1.76 ± 0.01)10-5. Similarly were determined the rates of the formolysis of the following compounds in 0.03151M HCO2Na in HCO2H (same data given): VII, 50.00°, 2.75, (1.54 ± 0.08)10-6; VII, 75.00°, 2.75, (1.99 ± 0.03)10-5; X (without added HCO2Na), 75.00°, 2.70, (3.35 ± 0.01)10-5; X, 75.00°, 2.68, (3.43 ± 0.03)10-5; X, 100.20°, 2.68, (3.13 ± 0.07)10-4; XI, 50.00°, 2.70, (5.03 ± 0.18)10-6; XI, 75.00°, 2.70, (6.08 ± 0.11)10-5; XII, 50.00°, 2.24, (2.58 ± 0.02)10-5; XII, 75.00°, 2.24, (3.40 ± 0.06)10-4; XVII, 25.00°, 3.13, (5.43 ± 0.10)10-5; XVIII, 25.00°, 3.63, (1.36 ± 0.13)10-4; XIII, 50.00°, 2.70, (2.90 ± 0.08)10-8; XIII, 75.00°, 2.70, (3.39 ± 0.02)10-5; XVa, 75.00, 2.69, (3.63 ± 0.11)10-5. The enthalpy (in kcal./mole) and the entropy (in e.u.) of the acetolysis were: VII, 24.0, -17.5; X, 23.9, -16.8; XI, 24.4, -15.0; XII, 25.0, -10.7; XIII, 23.8, -17.1; XVa, 23.9, -16.7; the same values for the formolysis were: VII, 22.2, -16.6; X, 22.0, -16.2; XI, 21.6, -16.1; XII, 22.4, -10.4; XIII, 21.3, -18.2. IX (18.4 g.) and 3.40 g. HCO2Na in 900 cc. dry HCO2H heated 6 hrs. at 75.0°, diluted with H2O, and extracted with Et2O, the extract washed, dried, and reduced with 2 g. LiAlH4, and the Et2O solution worked up gave a crude product which chromatographed on 500 g. Al2O3 and eluted with 5 l. pentane yielded 5.5 g. 2,3-dimethoxytetrahydronaphthalene (XIX), b2 102-5°, nD25 1.5454 (this material crystallized after several months, m. 36.5-38°; it gave with Br a monobromide, m. 78-80°). An addnl. 0.8 g. XIX, b3 110°, nD25 1.5401, was obtained by further elution with 4 l. Et2O; the column then eluted with 3 l. MeOH gave 0.7 g. V, b3 130°, which was converted to 0.8 g. VI, m. 49-51° (2nd crop, 0.1 g., m. 48-51°). XIX (2 g.) and 6 g. chloranil refluxed 15 hrs. in 20 cc. xylene yielded 1,3-C10H6(OMe)2 (XX), isolated as 0.8 g. picrate, m. 141-2°. V (2 g.) in 150 cc. 98-100% HCO2H heated 15 hrs. at 75° and the mixture worked up as described for the solvolysis run yielded 1.65 g. unchanged V, b2 150-2°, nD25 1.5296. V (0.5 g.) in 30 cc. 0.0315M HCO2Na in HCO2H heated 10 hrs. at 75° gave 0.35 g. unchanged V which yielded 0.40 g. VI, m. 50-3°. 1,3,2-(HO)2C10H5CO2Et (13 g.) treated with CH2N2 [from 15 g. H2NCON(NO)Me] in 200 cc. Et2O, the mixture allowed to stand overnight, the Et2O evaporated, the residual oil distilled, the distillate (11 g.), b2 155-75°, refluxed with 10 g. NaOH in 15 cc. H2O and 15 cc. EtOH overnight, the dark solution and solid treated with H2O and extracted with Et2O, and the residue from the extract distilled gave 2.8 g. dark oil, b3 145-50°, which chromatographed on Al2O3 readily lost its color but soon became colored again on standing; the purified XX had nD25 1.6140; picrate, long orange-red needles, m. 140-1° (from Et2O). XI (8 g.) in 700 cc. 0.03022M HCO2Na in dry HCO2H heated 42 hrs. at 75°, diluted with H2O, and extracted with pentane, the extract evaporated, the residue reduced with 1 g. LiAlH4, and the product chromatographed on 100 g. Al2O3 and eluted with 700 cc. pentane gave 1.65 g. 7-methoxytetrahydronaphthalene, b1.5 76°, nD25 1.5414; further elution with 600 cc. Et2O gave 1.55 g. III, b1.5 118-19°, nD25 1.5239. Dry HCO2Na (3.4 g.) in 1000 cc. dry HCO2H treated at 75.0° with 18.5 g. purified X, kept 66 hrs. at 76.0°, cooled, poured into 3 l. H2O, and extracted with pentane, the residue from the extract reduced with 2 g. LiAlH4, and the product chromatographed on 500 g. Al2O3 yielded 1.10 g. tetrahydronaphthalene (XXI), b22 101-3°, nD25 1.5388, which dehydrogenated with chloranil gave 80% C10H8, m. 75-7°; further elution of the column with MeOH yielded 5.4 g. I, b1.5 87-90°, nD25 1.5191. I (2.0 g.) and 0.6 g. p-MeC6H4SO3H in 100 cc. dry HCO2H heated 67 hrs. at 75.0°, cooled, poured into H2O, and extracted with pentane, and the residue from the extract reduced with LiAlH4 yielded 1.7 g. unchanged I, b10 124-7°, nD25 1.5189. Pure X (20.0 g.) added to 1200 cc. dry AcOH at 100.0°, the solution kept 101 hrs. at 100.0°, cooled, poured into 3 l. H2O, and extracted with pentane, the residue from the extract reduced with LiAlH4, and the product chromatographed on Al2O3 yielded 0.35 g. XXI, b10 75°, nD25 1.5370, and 6.85 g. I, b2 about 100°, nD25 1.5205. II (11.0 g.), 11.4 g. p-MeC6H4SO3H, and 1 cc. Ac2O in 1200 cc. dry AcOH kept 140 hrs. at 100.0° and the mixture processed in the usual manner with LiAlH4 reduction gave 8.2 g. I, b8.5 120-3°, nD25 1.5202. XVII (9.2 g.) (93% pure) and 2.45 g. dry HCO2Na in 600 cc. dry HCO2H kept 43.5 hrs. at 25.0° and worked up in the usual way yielded 2.05 g. hydrocarbon fraction, b25 112-15°, nD25 1.5229, and 2.20 g. XVI, b1.5 95-100°, nD25 1.5107. A 0.75-g. sample of the hydrocarbon fraction (containing 30% olefin) added to 1.0 g. OsO4 in 20 cc. Et2O containing 2 drops pyridine, kept 0.5 hr., treated with 150 cc. CH2Cl2, 2.5 g. KOH, and 2.5 g. mannitol in 50 cc. H2O, and shaken 2 hrs., the aqueous phase extracted with CH2Cl2, and the combined CH2Cl2 solutions worked up gave 0.4 g. 1-C10H7Me 55°, nD25 1.5323. XVI (5.0 g.) and 0.35 g. HCO2Na in 500 cc. HCO2H kept 41 hrs. at 25.0°, the mixture processed in the usual manner, and the product reduced with 1.5 g. LiAlH4 yielded 5.0 g. unchanged XVI, b8 117-20°, nD25 1.5108. XVI (4.4 g.) in 500 cc. HCO2H kept 27 days at 25° gave 0.06 g. hydrocarbon fraction and 4.0 g. XVI, b30 145-8°, nD25 1.5106. Olefin-hydrocarbon mixture (1.0 g.) from the solvolysis of XVII kept 42.5 hrs. at 25.0° with 0.050 g. pure HCO2Na in 150 cc. 98-100% HCO2H gave 0.95 g. product, nD25 1.5231, containing 26% olefin. Ph(CH2)3CH:CH2 (4.4 g.), b. 77-8°, nD25 1.5019, in 500 cc. 98-100% HCO2H kept 27 days at 25.0°, poured into H2O, and extracted with pentane, the residue from the extract reduced with LiAlH4, and the product chromatographed yielded 3.2 g. hydrocarbon, b30 106-8°, nD25 1.5054, and 1.0 g. alc., b2 95°, nD25 1.5099.

Journal of the American Chemical Society published new progress about Acetolysis. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Related Products of 52244-70-9.

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

Matier, W. L.; Comer, W. T.; Deitchman, D. published the artcile< Sulfamoyl azides. Hydrolysis rates and hypotensive activity>, Category: ethers-buliding-blocks, the main research area is sulfamoyl azide hypotensive; blood pressure sulfamoyl azide.

Monosubstituted sulfamoyl azides, e.g. N-(1-adamantyl)sulfamoyl azide (I) [33713-04-1] and N-(p-chlorophenyl)sulfamoyl azide (II) [13479-10-2], were significantly hypotensive in dogs at a min. ED of 0.005-0.01 mg/kg i.v., which was 1-3% of the dose required for disubstituted compounds I and II rapidly lowered blood pressure in dogs after oral administration of 1 mg/kg; the hypotensive response was apparently due to a decrease in both total peripheral resistance and aortic blood flow. The difference in hypotensive activity of mono- and disubstituted compounds appeared to be due to rapid release of azide [14343-69-2] from the former in neutral aqueous media. The mechanism and kinetics of hydrolysis were discussed. Related sulfamide derivatives were inactive. I was synthesized by reacting 1-adamantylamine with SO2Cl2 to form the sulfamoyl chloride, followed by reaction with NaN3 in dry MeCN.

Journal of Medicinal Chemistry published new progress about Antihypertensives. 10305-42-7 belongs to class ethers-buliding-blocks, and the molecular formula is C3H8ClNO2S, Category: ethers-buliding-blocks.

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

Tait, Annalisa; Luppi, Amedeo; Avallone, Rossella; Baraldi, Mario published the artcile< 2,1,3-Benzothiadiazine derivatives: synthesis and screening versus PDE4 enzyme>, Application In Synthesis of 10305-42-7, the main research area is benzothiadiazine derivative preparation PDE4 inhibitor structure screening; antioxidant structure phosphodiesterase 4 inhibitor benzothiadiazine derivative.

A series of N-1,3 disubstituted 2,1,3-benzothiadiazine derivatives (BTDs) were synthesized and evaluated for their inhibitory activity vs. enzymic isoform PDE4 extracted from U937 cell line. Some of the tested compounds showed a high PDE4 inhibitory activity at 100 μM and the IC50 value of the most interesting terms were evaluated. The structure-activity relationships of these compounds showed that the 3,5-di-tert-butyl-4-hydroxybenzyl moiety at N-1 position is important to obtain activity at micromolar level as previously reported. For the same compounds the antioxidant activity were evaluated highlighting 14 as the most significative one. The introduction of other bulky substituents in N-1 position is detrimental.

Farmaco published new progress about Antioxidants. 10305-42-7 belongs to class ethers-buliding-blocks, and the molecular formula is C3H8ClNO2S, Application In Synthesis of 10305-42-7.

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

McNeice, Peter; Vallana, Federico M. F.; Coles, Simon J.; Horton, Peter N.; Marr, Patricia C.; Seddon, Kenneth R.; Marr, Andrew C. published the artcile< Quinine based ionic liquids: A tonic for base instability>, Formula: C3H7BrO, the main research area is quinine ionic liquid catalyst preparation crystal structure; malononitrile benzaldehyde quinine catalyst Knoevenagel condensation.

Six basic ionic liquids were synthesized from the natural mol. quinine, including one room temperature ionic liquid The thermal properties were studied and the basicity analyzed by Hammett measurements. The properties are discussed in relation to the crystal structure of one of the salts, [C4Qn][NTf2] and electron d. models generated using Spartan. The ionic liquids were shown to catalyze the Knoevenagel condensation of malononitrile and benzaldehyde.

Journal of Molecular Liquids published new progress about Crystal structure. 6482-24-2 belongs to class ethers-buliding-blocks, and the molecular formula is C3H7BrO, Formula: C3H7BrO.

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

Xiong, Ni; Li, Yang; Zeng, Rong published the artcile< Iron-Catalyzed Photoinduced Remote C(sp3)-H Amination of Free Alcohols>, Safety of 4-(4-Methoxyphenyl)-1-butanol, the main research area is alkanol diazene iron catalyst regioselective photoredox amination; aminoalkanol preparation.

A general photocatalytic protocol for the remote C(sp3)-H bond amination of free alkanols was reported. The electron transfer between the abundant and inexpensive catalyst FeCl3 and simple alkanols under blue LED irradiation enabled the alkoxy radical formation under mild redox-neutral conditions, without addnl. oxidant and prefunctionalization. The subsequent selective 1,5-hydrogen atom transfer (HAT) and amination provided a simple and efficient way to access mol. complexity from readily available and bulk alcs.

Organic Letters published new progress about Aliphatic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Safety of 4-(4-Methoxyphenyl)-1-butanol.

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

Liang, Yuwei; Niu, Linbin; Liang, Xing-An; Wang, Shengchun; Wang, Pengjie; Lei, Aiwen published the artcile< Electrooxidation-Induced C(sp3)-H/C(sp2)-H Radical-Radical Cross-Coupling between Xanthenes and Electron-Rich Arenes>, Safety of 2-Methoxy-N-methylaniline, the main research area is xanthene aryl preparation; arene electrooxidation radical cross coupling xanthene.

Herein, an electrooxidation-induced alkylation of electron-rich arenes, such as anilines, imidazo[1,2-a]pyridines, etc., with xanthenes with H2 evolution under exogenous oxidant-free conditions, avoiding the utilization of metal catalysts, is reported. This protocol is well performed with various electron-rich aniline derivatives and nitrogen-containing heterocyclic compounds This electro-oxidative C(sp3)-H arylation represents an important expansion for the classic arenes alkylation, thereby proving that an attractive strategy for the developments of radical cross-coupling chem. was anticipated.

Chinese Journal of Chemistry published new progress about Alkylation. 10541-78-3 belongs to class ethers-buliding-blocks, and the molecular formula is C8H11NO, Safety of 2-Methoxy-N-methylaniline.

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

Schmidt, Ulrike; Theumer, Gabriele; Jaeger, Anne; Kataeva, Olga; Wan, Baojie; Franzblau, Scott G.; Knoelker, Hans-Joachim published the artcile< Synthesis and activity against Mycobacterium tuberculosis of olivacine and oxygenated derivatives>, HPLC of Formula: 56724-03-9, the main research area is olivacine oxygenated derivative preparation antitubercular; catalysis; cyclization; inhibitory activity; olivacine; palladium; pyrido[4,3-b]carbazoles.

The tetracyclic pyrido[4,3-b]carbazole olivacine I and its four oxygenated derivatives have been synthesized by a late-stage palladium-catalyzed Heck-type cyclization of the pyrrole ring as a key step. All the final compounds were evaluated for their antitubercular activity. In a test for the inhibition of the growth of Mycobacterium tuberculosis, 9-methoxyolivacine showed the most significant inhibitory activity against Mycobacterium tuberculosis, with an MIC90 value of 1.5 μM.

Molecules published new progress about Aromatic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, HPLC of Formula: 56724-03-9.

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