Tag: M.W=200-250

Wang, Yaxin published the artcileVisible-Light-Promoted Site-Specific and Diverse Functionalization of a C(sp³)-C(sp³) Bond Adjacent to an Arene, Synthetic Route of 20029-52-1, the publication is ACS Catalysis (2020), 10(12), 6603-6612, database is CAplus.

A strategy for inert C-C bond functionalization is reported. Site-specific cleavage and functionalization of saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process was achieved. The general features of this reaction are: 1-Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized; 2-One carbon is converted into ketone, and the another can be tunably converted into nitrile, peroxide or halide; 3-The typical conditions includes: 1.0 mol% Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask and room temperature These reactions offer a powerful tool to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions make these transformations valuable and attractive.

ACS Catalysis published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C9H10O3S, Synthetic Route of 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Koshel, S. G. published the artcileSynthesis of biphenylpolycarboxylic acids. II. Oxidation of cyclohexyltoluenes and methylbiphenyls to carboxylic acids, Category: quinuclidine, the publication is Zhurnal Organicheskoi Khimii (1992), 28(2), 363-6, database is CAplus.

Oxidation of 2-, 3-, and 4-cyclohexyltoluenes and -PhC₆H₄Me with O at 90° in AcOH containing Co(OAc)₂-MeCHO or Mn(OAc)₂-NaBr, resp., gave the corresponding title acids in 95-98% yield. The substrate reactivity increased in the stated order of isomers, owing to steric hindrance in the ortho isomers.

Zhurnal Organicheskoi Khimii published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Category: quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Sun, Yong-Hui published the artcileA diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp²)-H hydroxylation strategy, SDS of cas: 20029-52-1, the publication is Chemical Science (2016), 7(3), 2229-2238, database is CAplus and MEDLINE.

Hydroxylated benzanilides such as I (R¹ = H, 4-Me, 3-F, etc.; R² = H, 4-Me, 3-F, etc.; R³ = Me, Et, Bn) were prepared by chemo- and regioselective C(sp²)-H hydroxylation using palladium and ruthenium catalysts. Ruthenium catalysts yielded N-aryl hydroxybenzamides, while palladium catalysts yielded N-hydroxyaryl benzamides. Computational investigations reveals that the regioselectivity is controlled mainly by both steric and electronic factors. Steric effects determine the regioselective outcomes in the Ru-catalyzed reaction, while electronic effects are dominant in the Pd-catalyzed reaction.

Chemical Science published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C48H47FeP, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Shabarov, Yu. S. published the artcileCyclopropanes and cyclobutanes. LVIII. p-Bicyclo[n.1.0]alk-1-ylbenzoic acids and -anilines, Name: 4-Cyclohexylbenzoic acid, the publication is Zhurnal Organicheskoi Khimii (1968), 4(7), 1175-80, database is CAplus.

The oxidation of p-RC6H4COMe (I) with NaOBr gave p-RC6H4CO2H (II). The reaction of II with SOCl2 gave the corresponding acid chlorides which were treated with NH4OH to give p-RC6H4CONH2. The action of NaOBr on the amides gave p-RC6H4NH2 (III). The alternative preparation of III involved converting I to p-RC6H4C(:NOH)Me, which with PCl5 were rearranged to p-RC6H4NHAc (IV). Saponification of IV gave III. Most III were converted to p-RC6H4NHC(:S)NHPh (by treating with PhN:C:S) for the identification purposes. The II and III prepared were (R in II and III given): cyclohexyl, cyclopentyl, bicyclo[3.1.0]hex-1-yl, and bicyclo[4.1.0]hept-1-yl. Their pK values and Hammett constant were determined

Zhurnal Organicheskoi Khimii published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C9H4F6O, Name: 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Sugimoto, Yuka published the artcileEvaluation of heat resistance of metal-resin bonding using epoxy monoliths prepared with various epoxy resins and diamine curing agents, Safety of 4,4-Diaminodicyclohexyl methane, the publication is Nippon Setchaku Gakkaishi (2020), 56(8), 303-313, database is CAplus.

Epoxy monoliths with a co-continuous porous structure were produced by a thermosetting reaction using combinations oi 4 kinds of epoxy resins, 9 kinds of diamine curing agents, and 2 kinds porogens (pore forming agents), and applied to dissimilar materials bonding between metals and engineering plastics. An epoxy monolith was prepared on a stainless or copper plate, and a polycarbonate or poly (phenylene sulfide) plate was thermally welded to prepare a bonding test piece. The heat resistance of the epoxy monolith bonding systems used in this study was evaluated from the results of the tensile shear test before and after heat treatment. In addition, the thermogravimetric anal. of the monolith materials revealed the thermal decomposition behavior of the cured epoxy. Based on these results, the effects of the structure and the number of functional groups of the epoxy resins and the diamine curing agents on the porous structure bonding strength, and heat resistance of the epoxy monoliths were discussed.

Nippon Setchaku Gakkaishi published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C14H17FN4O3, Safety of 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Sakata, Nanako published the artcileInterfacial Structure Control and Three-Dimensional X-ray Imaging of an Epoxy Monolith Bonding System with Surface Modification, HPLC of Formula: 1761-71-3, the publication is Langmuir (2020), 36(37), 10923-10932, database is CAplus and MEDLINE.

A monolith bonding system has a high reliability for dissimilar material bonding. The epoxy monolith layer fabricated on a substrate guarantees bond strength by the anchor effect, regardless of the compatibility of the used materials. Designing a high-performance monolith bonding system requires the suppression of an interfacial failure between the monolith and the substrate. In this study, silane and phosphine coupling agents containing amino and epoxy groups were used to construct a robust interfacial structure between the monolith and the substrates such as glass and metals. The internal and interfacial monolith structures were characterized by three-dimensional X-ray imaging as a nondestructive observation method in addition to the SEM of the sample cross sections. The modification of the substrate-monolith interface using the coupling agents improved the strength of dissimilar material bonding of the glass and metal substrates in combination with thermoplastic resins such as poly(ethylene terephthalate) and polycarbonate bisphenol-A.

Langmuir published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, HPLC of Formula: 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Kubosaki, Suzuka published the artcileVisible- and UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts, Name: 4-Cyclohexylbenzoic acid, the publication is Journal of Organic Chemistry (2020), 85(8), 5362-5369, database is CAplus and MEDLINE.

Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, resp. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only two-mol. organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.

Journal of Organic Chemistry published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Name: 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Dauben, Wm. G. published the artcileThe hydrogenation of 4-hydroxybiphenylcarboxylic acids, Product Details of C13H16O2, the publication is Journal of the American Chemical Society (1953), 4969-73, database is CAplus.

When p-(p-HOC₆H₄)H₆H₄CO₂H (I) was hexahydrogenated over Raney Ni in alkali, reaction occurred only in the HO-substituted ring and both a cis and a trans isomer were isolated. The perhydrogenation yielded only 1 pure product which was shown to have the trans configuration in the CO₂H-substituted ring. When m-(p-HOC₆C₄)C₆H₄CO₂H (II) was hexahydrogenated, again reaction occurred only in the HO-substituted ring but only 1 isomer was isolated. p-(p-MeOC₆H₄C₆H₄)CO₂H (40 g.) heated 15 hrs. under N with 525 cc. AcOH and 105 cc. 48% HBr, 300 cc. solvent distilled off in vacuo, the residual solution diluted with 300 cc. H₂O, cooled, and the crude product (35 g.) recrystallized from dioxane, cyclohexane, and then dilute AcOH gave 30 g. (80%) I, m. 288-90° (uncorrected). I (4.0 g.), 1.0 g. Na₂CO₃, and 2 cc. Raney Ni W-2 suspended in 31 cc. H₂O, the mixture hydrogenated 6 hrs. at 125° and 2500 lb. pressure and then 0.75 hr. at 150°, filtered, the filtrate (150 cc.) acidified with excess concentrated HCl, the precipitate (2.9 g.), m. 220-32°, refluxed 8 hrs. with 100 cc. MeOH and 2 cc. concentrated H₂SO₄, the solution concentrated to 25 cc., diluted with H₂O, the organic layer dissolved in Et₂O, the solution washed twice with 5% aqueous Na₂CO₃, extracted with two 20-cc. portions of cold 10% aqueous KOH, and the alk. extract refluxed 2 hrs. and then acidified gave 1.2 g. (30%) pure I, m. 290-1° (from aqueous AcOH)(all m.ps. are corrected). The Et₂O solution evaporated, the residue refluxed 6 hrs. with 40 cc. 10% alc. KOH, and the mixture acidified gave a mixture of the cis (III) and trans (IV) isomers of 4-(4-hydroxycyclohexyl)benzoic acid, m. 167-73°. The mixture dissolved in 15 cc. warm N aqueous NaOH, treated with 6 g. NaNO₃ in 10 cc. H₂O, cooled, filtered, and the filter cake washed with a small amount of cold H₂O, dissolved in 10 cc. hot H₂O, and acidified gave 0.29 g. (10%) IV, m. 228.5-34.5° [analytical sample, m. 235-7° (from Me₂CO)]; the filtrate from the IV acidified gave 1.31 g. (45.5%) III, m. 175-87° [analytical sample, m. 194.0-5.7° (from Me₂CO)]. I (2.14 g.)in 1.5 g. KOH and H₂O and 3 cc. W-5 Raney Ni diluted with H₂O to 31 cc., the mixture hydrogenated as before, filtered, and acidified gave 1.9 g. acids, m. 175-200°; the acids in 15 cc. warm N NaOH treated with 5 g. NaNO₂, the mixture cooled, the precipitate dissolved in hot H₂O, and the solution acidified gave 0.65 g. (42.5%) IV, m. 230-5°; the filtrate acidified yielded 1.15 g. mixture of I and III, which was fractionally crystallized from Me₂CO to yield 0.45 g. (29.4%) III, m. 187-93°; the mother liquor evaporated to dryness and the residue recrystallized from dilute AcOH yielded 0.65 I, m. 285-91°. The hydrogenation of 4.0 g. I with 3-months old W-2 Raney Ni under the same conditions 4 hrs. yielded 1.27 g. (37.5%) IV, 0.63 g. (18.6%) III, and 0.7 g. I. III (0.22 g.) heated 6 hrs. on the steam bath with 3 cc. glacial AcOH saturated with HBr, the solution poured into 30 cc. cold. H₂O, extracted with 20 cc. CHCl₃, the extract washed with H₂O, dried with MgSO₄, evaporated, the residue dissolved in 30 cc. MeOH containing 0.06 g. Na, hydrogenated 3 hrs. over 3 cc. Raney Ni at 40 lb. initial pressure, the mixture filtered, the filtrate evaporated to dryness, the residue dissolved in H₂O, acidified with excess concentrated HCl, and heated on the steam bath, and the precipitate recrystallized from petr. ether and dilute EtOH gave 4-cyclohexylbenzoic acid (V), m. 195-6°. IV (0.22 g.) gave similarly 130 mg. (64%) V. IV (0.22 g.) in 5 cc. glacial AcOH treated dropwise during 1 hr. with stirring with 0.138 g. CrO₃ in 14 cc. H₂O and 0.7 cc. AcOH, the mixture stirred 2 hrs., treated with 2 cc. MeOH, poured into 150 cc. H₂O containing 5 cc. concentrated HCl, extracted with 30 cc. CHCl₃, and the extract washed with H₂O, dried, and evaporated gave 180 mg. (82.5%) 4-(4-oxocyclohexyl)benzoic acid (VI), m. 227.5-30.5°. III (0.275 g.) yielded similarly 204 mg. (74%) VI, m. 228-31°. I (4.0 g.), 2.1 g. KOH in H₂O, and 4 cc. W-5 Raney Ni diluted to 31 cc. with H₂O, and the mixture hydrogenated 10 hrs. at 150° and 2500 lb. pressure gave similarly 2.3 g. (54.5%) 4-(4-hydroxycyclohexyl)cyclohexanecarboxylic acid (VII), m. 173.7-4.7° (from Me₂CO). VII (0.5 g.) heated 7 hrs. on the steam bath with 5 cc. glacial AcOH saturated with HBr, the solution poured into H₂O, the oily solid extracted with 100 cc. CHCl₃, the extract washed with H₂O, dried, evaporated, the residual oil in 50 cc. MeOH containing 0.2 g. Na and 3 cc. Raney Ni hydrogenated 6 hrs. at 40 lb. initial pressure, the mixture filtered, evaporated to dryness, the residue dissolved in H₂O, the solution acidified, the precipitate extracted with two 50-cc. portions Et₂O, the extract washed, dried, evaporated, and the residue crystallized from petr. ether gave 350 mg. (76.9%) trans-4-cyclohexylcyclohexanecarboxylic acid, m. 159-60° (from petr. ether); amide, m. 199-200°. VII (0.5 g.) in 9 cc. glacial AcOH oxidized similarly with 0.41 g. CrO₃ in 0.4 cc. H₂O and 0.9 cc. AcOH yielded 350 mg. (70.8%) trans-4-(4-oxocyclohexyl)cyclohexanecarboxylic acid, m. 174-6.5° (from pert. ether). p-BrC₆H₄OMe (200 g.) in 350 cc. dry Et₂O added dropwise to 26 g. Mg in 200 cc. dry Et₂O containing 1 cc. purified EtI at such a rate as to keep the mixture gently refluxing, the mixture refluxed 1 hr., cooled, treated rapidly with stirring with 180 g. 3-methylcyclohexanone in 200 cc. dry Et₂O, stirred 1 hr., decomposed with excess cold N H₂SO₄, the Et₂O layer washed with H₂O, dried, distilled, the residue dissolved in 200 cc. glacial AcOH, added to 10 cc. Ac₂O and 2 g. 2-C₁₀H₇SO₃H, the mixture refluxed 1 hr., poured into H₂O, extracted with 500 cc. Et₂O, and the extract dried and fractionated gave 147 g. (65.5%) impure 4-methoxy-3′-methyl-3′,4′,5′,6′-tetrahydrobiphenyl (VIII), b₆ 144-6°. VIII (145 g.) heated with 28.25 g. S at 225°, the temperature gradually raised during 3.5 hrs. to 240°, the mixture cooled, the hard red solid dissolved in Et₂O, the solution evaporated, and the residue distilled gave 116.7 g. (81%) m-(p-MeOC₆H₄)C₆H₄Me (IX), pale yellow distillate, b₄ 139-41°, which crystallized from dilute EtOH in colorless plates, m. 51-2°. IX (40 g.) in 800 cc. pyridine and 800 cc. H₂O heated with stirring on the steam bath, the mixture treated during 3.5 hrs. with 127 g. KMnO₄ in portions, filtered, the MnO₂ digested on the steam bath with 300 cc. 50% aqueous Me₂CO, the combined filtrates concentrated to 600 cc., washed with 500 cc. Et₂O, cautiously acidified to Congo red with concentrated HCl, and the precipitate recrystallized from dilute AcOH gave 24 g. (97%) m-(p-MeOC₆H₄)C₆H₄CO₂H (X), m. 202-3°; evaporation of the Et₂O washing yielded 18 g. IX. X treated with excess CH₂N₂ gave the Me ester, m. 70-1.5° (from petr. ether). X (20 g.) refluxed 13 hrs. under N with 250 cc. glacial AcOH and 75 cc. 48% HBr, the solution concd, to 0.5 volume in vacuo, diluted with H₂O, cooled, and the solid deposit recrystallized from dilute AcOH gave 16.5 g. (88%) II, m. 241-2°. II (2.46 g.), 0.85 KOH, and 3 cc. W-5 Raney Ni diluted with H₂O to 31 cc., hydrogenated 1 hr. at 75° and an initial pressure of 2500 lb., the mixture filtered, the filtrate acidified, extracted with Et₂O, the residue from the extract esterified with 100 cc. MeOH and 2 cc. concentrated H₂SO₄, and the phenolic and nonphenolic fractions separated and processed as described for I yielded 1 g. II and 1.6 g. (63.5%) m-(4-hydroxycyclohexyl)benzoic acid, m. 150-1.8° (from Et₂O-hexane); the similar hydrogenation of II in 1 equivalent aqueous Na₂CO₃ gave the same yield of the hexahydro derivative

Journal of the American Chemical Society published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Product Details of C13H16O2.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Khodaverdian, Verjine published the artcileDeferiprone: Pan-selective Histone Lysine Demethylase Inhibition Activity and Structure Activity Relationship Study, Synthetic Route of 1761-71-3, the publication is Scientific Reports (2019), 9(1), 1-17, database is CAplus and MEDLINE.

Deferiprone (DFP) is a hydroxypyridinone-derived iron chelator currently in clin. use for iron chelation therapy. DFP has also been known to elicit antiproliferative activities, yet the mechanism of this effect has remained elusive. We herein report that DFP chelates the Fe²⁺ ion at the active sites of selected iron-dependent histone lysine demethylases (KDMs), resulting in pan inhibition of a subfamily of KDMs. Specifically, DFP inhibits the demethylase activities of six KDMs – 2A, 2B, 5C, 6A, 7A and 7B – with low micromolar IC₅₀s while considerably less active or inactive against eleven KDMs – 1A, 3A, 3B, 4A-E, 5A, 5B and 6B. The KDM that is most sensitive to DFP, KDM6A, has an IC₅₀ that is between 7- and 70-fold lower than the iron binding equivalence concentrations at which DFP inhibits ribonucleotide reductase (RNR) activities and/or reduces the labile intracellular zinc ion pool. In breast cancer cell lines, DFP potently inhibits the demethylation of H3K4me3 and H3K27me3, two chromatin posttranslational marks that are subject to removal by several KDM subfamilies which are inhibited by DFP in cell-free assay. These data strongly suggest that DFP derives its anti-proliferative activity largely from the inhibition of a sub-set of KDMs. The docked poses adopted by DFP at the KDM active sites enabled identification of new DFP-based KDM inhibitors which are more cytotoxic to cancer cell lines. We also found that a cohort of these agents inhibited HP1-mediated gene silencing and one lead compound potently inhibited breast tumor growth in murine xenograft models. Overall, this study identified a new chem. scaffold capable of inhibiting KDM enzymes, globally changing histone modification profiles, and with specific anti-tumor activities.

Scientific Reports published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Synthetic Route of 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Kalita, Deep J. published the artcileNovel bio-based epoxy resins from eugenol as an alternative to BPA epoxy and high throughput screening of the cured coatings, Application In Synthesis of 1761-71-3, the publication is Polymer (2021), 124191, database is CAplus.

A novel vinyl ether monomer from eugenol, 2-eugenoloxyvinyl ether (EEVE), was synthesized and used as a building block for polymeric epoxy resins. The EEVE monomer was polymerized via cationic polymerization of the vinyl ether group leaving the allylic functionality of eugenol available for further epoxidation Epoxidized poly(EEVE) resins varying in levels of epoxidation (epoxy equivalent weights from 360 to 870 g/equiv) were produced and cured with twelve amine curatives at ambient and elevated temperatures for different time intervals to evaluate and optimize the curing regime. The cured coatings were screened with high throughput dye extraction and “conventional” coating testing methods and compared to coatings produced from diglycidyl ether of bisphenol-A (DGEBA). Results showed that coatings derived from epoxidized poly(EEVE) [Epoly(EEVE)] can be tuned from soft and elastic with hardness <50 GPa and glass transition temperatures (T_gs) <20° to hard and brittle with hardness >500 GPa and T_gs>60° by varying the extent of epoxidation and the nature of curative, whereas DGEBA resulted in hard and brittle coatings irresp. of the type of curative used in the study. Compared to DGEBA resin, coatings with similar or higher crosslink densities and hardness were obtained from Epoly(EEVE) resins with >50% epoxidation of EEVE moieties using the same curative and curing regime. These partially biobased epoxy compounds derived from eugenol have the potential to be competitive with petroleum-based DGEBA resins in coatings applications.

Polymer published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Application In Synthesis of 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider