Tag: M.W=200-250

Zhao, Guohua published the artcileSynthesis of potent and selective 2-azepanone inhibitors of human tryptase, Quality Control of 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(2), 309-312, database is CAplus and MEDLINE.

The serine protease tryptase has been associated with a broad range of allergic and inflammatory diseases and, in particular, has been implicated as a critical mediator of asthma. The inhibition of tryptase therefore has the potential to be a valuable therapy for asthma. The synthesis, employing solution phase parallel methods, and SAR of a series of novel 2-azepanone tryptase inhibitors are presented. One member of this series, I, was identified as a potent inhibitor of human tryptase (IC₅₀ 38 nM) with selectivity ≤330-fold vs. related serine proteases (trypsin, plasmin, uPA, tPA, APC, alpha-thrombin, and FXa).

Bioorganic & Medicinal Chemistry Letters 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 C8H7ClO3, Quality Control of 20029-52-1.

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

Singh, Ritesh published the artcileP450-Catalyzed Intramolecular sp³ C-H Amination with Arylsulfonyl Azide Substrates, COA of Formula: C13H16O2, the publication is ACS Catalysis (2014), 4(2), 546-552, database is CAplus and MEDLINE.

The direct amination of aliphatic C-H bonds represents a most valuable transformation in organic chem. While a number of transition-metal-based catalysts have been developed and investigated for this purpose, the possibility to execute this transformation with biol. catalysts has remained largely unexplored. Here, we report that cytochrome P 450 enzymes can serve as efficient catalysts for mediating intramol. benzylic C-H amination reactions in a variety of arylsulfonyl azide compounds Under optimized conditions, the P 450 catalysts were found to support up to 390 total turnovers leading to the formation of the desired sultam products with excellent regioselectivity. In addition, the chiral environment provided by the enzyme active site allowed for the reaction to proceed in a stereo- and enantioselective manner. The C-H amination activity, substrate profile, and enantio/stereoselectivity of these catalysts could be modulated by utilizing enzyme variants with engineered active sites.

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 C17H14O5, COA of Formula: C13H16O2.

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

Eaton, Matthew D. published the artcileTemperature dependent fracture behavior in model epoxy networks with nanoscale heterogeneity, Application In Synthesis of 1761-71-3, the publication is Polymer (2021), 123560, database is CAplus.

The role of nanoscale heterogeneity on the mode I fracture toughness, K_Ic, of model epoxy networks has been investigated. Model systems utilized consist of diglycidyl ether of bisphenol A (DGEBA) as the epoxide with a stoichiometric amine mixture of a rigid cycloaliphatic diamine (PACM) and a more flexible, polypropylene glycol based diamine (Jeffamine) at different molar ratios. The mol. weight of the Jeffamine was adjusted to further tailor the epoxy properties. Fracture toughness was measured using single edge notched bend samples and hardness was measured by Vickers indentation. Both measurements were performed at temperatures as low as -100°C to above ambient temperatures Results are interpreted in the context of the Dugdale model of material toughness where the fracture toughness is expressed in terms of a cohesive zone stress (related to the hardness), the elastic modulus (measured directly) and the crack tip opening displacement (obtained from images of the fracture surfaces). High toughness is obtained in heterogeneous networks where a decrease in the cohesive zone stress is offset by sufficiently large increases in the crack tip opening displacement.

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

Habicht, J. published the artcileInhibition of prostaglandin E₂ release by salicylates, benzoates and phenols: a quantitative structure-activity study, SDS of cas: 20029-52-1, the publication is Journal of Pharmacy and Pharmacology (1983), 35(11), 718-23, database is CAplus and MEDLINE.

Concentrations inhibiting 50% of PGE₂  [363-24-6] release from phorbol ester-stimulated mouse peritoneal macrophages in vitro were determined for monosubstituted congeners of salicylic acid, benzoic acid, and phenol. Other compounds, mainly benzoic acids, were inactive. An attempt was made to establish QSAR from the exptl. data using literature or calculated values for the logarithmic octanol-water partition coefficients of the compounds, molar refractivity and sigma values of substituents as well as structural indicator variables. The equations had moderate predictive power and should be considered as a 1st step in the investigation of factors determining the biog. activity of salicylates, benzoates, and phenols.

Journal of Pharmacy and Pharmacology 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, SDS of cas: 20029-52-1.

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

Yan, Lin published the artcile2-Aryl(pyrrolidin-4-yl)acetic acids are potent agonists of sphingosine-1-phosphate (S1P) receptors, Application In Synthesis of 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(13), 3564-3568, database is CAplus and MEDLINE.

2-Aryl(pyrrolidin-4-yl)acetic acids I [R = i-Bu, cyclopentyl, cyclohexyl, F₃C(CH₂)₂, 3,3-difluoro-1-cyclopentyl, 4,4-difluoro-1-cyclohexyl] and II were synthesized and their biol. activities as agonists of S1P receptors were evaluated. These analogs were able to induce lowering of lymphocyte counts in the peripheral blood of mice and were found to have good overall pharmacokinetic properties in rats.

Bioorganic & Medicinal Chemistry Letters 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 C8H6ClNO, Application In Synthesis of 20029-52-1.

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

Buu-Hoi published the artcileChemistry of cyclohexylbenzene, COA of Formula: C13H16O2, the publication is Bulletin de la Societe Chimique de France (1944), 127-36, database is CAplus.

Cyclohexylbenzene (I) is an excellent starting material for organic syntheses; its derivatives crystallize readily, are soluble in most organic solvents; they are often cleaved by AlCl₃ (II), forming cyclohexyl radicals. Condensation of 15 g. I with 10 g. phthalic anhydride in 150 cc. of benzene (III), wi h 20 g. of II under cooling, yields after decomposition with HCl 2-(p-cyclohexylbenzoyl)benzoic acid (IV), m. 179-80° (from petr. ether). Reduction of IV with Zn and NH₄OH gives 2-(p-cyclohexylbenzyl)benzoic acid, m. 137° (from III). I condensed with succinic anhydride in PhNO₂, with II, gives β-(p-cyclohexylbenzoyl)propionic acid (V), m. 134° (from III). Clemmensen-Martin reduction of V gives γ-(p-cyclohexylphenyl)butyric acid (VI), b₁₈ 240°, m. 47° (from III + petr. ether); its acid chloride (VII), b_3-4 185-90°, treated with NH₃ yields the acid amide of VI, m. 128° (from III). Reaction of 6 g. of VII with 5 g. of II in III yields 3 g. of 7-cyclohexyl-1-tetralone (VIII), b₂₁ 222-4° (semicarbazone, m. 270-1°) (decomposition), some α-tetralone, and I, the latter being formed from cyclohexyl radicals and III. Clemmensen-Martin reduction of VIII yields 7-cyclohexyl-1,2,3,4-tetrahydronaphthalene (IX), b₂₀ 192-5°. Dehydrogenation of IX with Se at 335-40° for 15 h. is a good method for preparing 2-C₁₀H₇Ph. Heating equimolar amounts of VIII and isatin with 3 mols. of KOH for 24 h. on the steam cone in a min. of alc. gives 2-cyclohexyl-12-aza-7-benzanthracenecarboxylic acid (decomposition on heating). The Grignard reagent prepared from 145 g. p-bromocyclohexylbenzene yields with 30 g. of (CH₂)₂O at -10° 50 g. of 2-(p-cyclohexylphenyl)ethanol (X), b₁₄ 190-5°; phenylurethane, m. 100°. Treating 50 g. of X in CHCl₃ with 28 g. PBr₃ yields 30 g. of 2-(p-cyclohexylphenyl)-1-bromoethane (XI), b₁₄ 188-90°. Addition of 27 g. of XI to 18 g. of Et malonate (XII) in 25 cc. of absolute alc. containing 2.3 g. of Na yields 20 g. of Et [2-(p-cyclohexylphenyl)ethyl]malonate (XIII), b₁₅ 245-8°, saponified to VI. Addition of 10 g. of XI to a solution of 10 g. of PhCH(CO₂Et)₂ in 50 cc. of xylene and 1 g. of Na yields Et (phenyl(2-p-cyclohexylphenyl)malonate, b_3-4 245-55°, saponified to α-phenyl-γ-(p-cyclohexylphenyl)butyric acid (XIV), b_2.5 260°, m. 134° (from III). The acid chloride (XV) of XIV treated with NH₃ yields the amide of XIV m. 106-7°. Reaction of XV with II and III gives 2-phenyl-7-cyclohexyl-1-tetralone (XVI), b_2.7 240-50°, some I, and 2-phenyltetralone. Clemmensen reduction of XVI gives 2-phenyl-7-cyclohexyl-1,2,3,4-tetrahydronaphthalene, b_0.7 190-200°, dehydrogenated by Se to 2,7-diphenylnaphthalene, m. 142-3° (from alc.). KCN with p-(chloromethyl)cyclohexylbenzene (XVII) in EtOH results in a mixture of p-cyclohexylbenzyl Et ether, b₁₃ 175-7°, and (p-cyclohexylphenyl)acetonitrile (XVIII), b₁₂ 189-92°, m. 38°. Condensation of XVIII with p-ONC₆H₄NMe₂ by KOH gives p-C₆H₁₁C₆H₄ C(CN):NC₆H₄NMe₂ (XIX), m. 124-5°, and C₆H₁₁C₆H₄C(CN):̈ONC₆H₄NMe₂, m. 197-8° (from AcOH). Acid hydrolysis of XIX gives some C₆H₁₁C₆H₄COCN, m. 50° (petr. ether), and alk. hydrolysis leads to p-cyclohexylbenzoic acid, m. 197° (from AcOH). Condensation of 5 g. of XVIII with 2.8 g. of BzH (EtONa) gives α-(p-cyclohexylphenyl)cinnamonitrile (XX), m. 117° (alc.), and with 2.5 g. of furfural yields α-(p-cyclohexylphenyl)-2-furanacrylonitrile, m. 64°. These nitriles could not be hydrolyzed. Condensation of XX with III and II yields I and a mixture of PhCH(CN)CHPh₂ and Ph₂C(CN)CH₂Ph, not further purified. Saponification of XVIII with KOH gives (p-cyclohexylphenyl)acetic acid; its acid chloride (XXI), b₃ 165-6°, upon treatment with NH₃ gives (p-cyclohexylphenyl)acetamide, m. 163° (from III). XXI in III treated with II yields I, desoxybenzoin, and some p-cyclohexyldesoxybenzoin, b₁₆ 260-70°, m. 103° (from alc.). If the condensation is carried out in PhNO₂, 45 g. p,p’-dicyclohexyldesoxybenzoin, b_1.6 250-60°, m. 146°, is obtained and no cleavage of the cyclohexyl radical occurs. Condensation of XVII (45 g.) with 32 g. iso-PrCOPh previously treated with 8.9 g. NaNH₂ (XXII) in 200 cc. of III yields 47 g. of p-C₆H₁₁C₆H₄CH₂CMe₂Bz (XXIII), b₂ 223-6°. By treatment with XXII cleavage of XXIII to C₆H₁₁C₆H₄CH₂CMe₂CONH₂ (XXIV), m. 125°, is effected. NaOBr degradation of XXIV leads to the isocyanate, b₂ 145-50°, which upon treatment with HCl gives C₆H₁₁C₆H₄CH₂CMe₂NH₂.HCl; free base, b₃ 157-9°, m. 45° (from petr. ether); picrate, m. 175°; Bz derivative, m. 135°. To 90 g. of XII in 120 g. absolute alc. and 11 g. of Na, 100 g. of XVII was added, yielding 100 g. of Et (p-cyclohexylphenylmethyl) malonate, b₁₃ 230-2°; saponification yields the substituted malonic acid, m. 163° (with loss of CO₂). On distilling the acid, β-(p-cyclohexylphenyl)propionic acid (XXV), b_15-16 225-30°, m. 125° (from III), is obtained; its acid chloride (XXVI), b_2.5 170-2°, treated with NH₃ yields the amide of XXV, m. 167°. Reaction of 15 g. of XXVI with 50 cc. of III, with II catalyst, yields 7 g. of 6-cyclohexyl-1-indanone (XXVII), b_13-14 203-5°, m. 87° (semicarbazone, m. 230°), and some I and 1-indanone. XXVII condensed with isatin, with KOH, gives 3-cyclohexyl-5-aza-6,7-benzofluorene-8-carboxylic acid, decarboxylating on heating to 3-cyclohexyl-5-aza-6,7-benzofluorene, b₂ 240-50°, m. 129° (from alc.); picrate, decompose below 200°. Clemmensen reduction of XXVII yields 6-cyclohexylindan, b₁₆ 174-6°. Cyclohexyl p-nitrobenzoate, b₂ 180°, m. 52° (from alc.), prepared by treating p-O₂NC₆H₄COCl with excess of cyclohexanol, shows remarkable properties against pneumococci and tubercle bacilli.

Bulletin de la Societe Chimique de France 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, COA of Formula: C13H16O2.

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

Kinaci, Emre published the artcileEpoxidation of cardanol’s terminal double bond, Quality Control of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 2104, database is CAplus and MEDLINE.

In this investigation, the terminal double bonds of the side chain epoxidized cardanol glycidyl ether (SCECGE) mol. were further epoxidized in the presence of Oxone (potassium peroxomonosulfate) and fluorinated acetone. Regular methods for the double bond epoxidation are not effective on the terminal double bonds because of their reduced electronegativity with respect to internal double bonds. The terminal double bond functionality of the SCECGE was epoxidized to nearly 70%, increasing the epoxy functionality of SCECGE from 2.45 to 2.65 epoxies/mol. as measured using proton magnetic nuclear resonance (¹H-NMR). This modified material-side chain epoxidized cardanol glycidyl ether with terminal epoxies (TE-SCECGE)-was thermally cured with cycloaliphatic curing agent 4,4′-methylene bis(cyclohexanamine) (PACM) at stoichiometry, and the cured polymer properties, such as glass transition temperature (T_g) and tensile modulus, were compared with SCECGE resin cured with PACM. The T_g of the material was increased from 52 to 69°C as obtained via a dynamic mech. anal. (DMA) while the tensile modulus of the material increased from 0.88 to 1.24 GPa as a result of terminal double bond epoxidation In addition to highlighting the effects of dangling side groups in an epoxy network, this modest increase in T_g and modulus could be sufficient to significantly expand the potential uses of amine-cured cardanol-based epoxies for fiber reinforced composite applications.

Polymers (Basel, Switzerland) 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, Quality Control of 1761-71-3.

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

Kinaci, Emre published the artcileInfluence of epoxidized cardanol functionality and reactivity on network formation and properties, Computed Properties of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 1956, database is CAplus and MEDLINE.

Cardanol is a renewable resource based on cashew nut shell liquid (CNSL), which consists of a phenol ring with a C15 long aliphatic side chain in the meta position with varying degrees of unsaturation Cardanol glycidyl ether was chem. modified to form side-chain epoxidized cardanol glycidyl ether (SCECGE) with an average epoxy functionality of 2.45 per mol. and was cured with petroleum-based epoxy hardeners, 4-4′-methylenebis(cyclohexanamine) and diethylenetriamine, and a cardanol-based amine hardener. For comparison, cardanol-based diphenol diepoxy resin, NC514 (Cardolite), and a petroleum-based epoxy resin, diglycidyl ether of bisphenol-A (DGEBA) were also evaluated. Chem. and thermomech. analyzes showed that for SCECGE resins, incomplete cure of the secondary epoxides led to reduced cross-link d., reduced thermal stability, and reduced elongation at break when compared with difunctional resins containing only primary epoxides. However, because of functionality greater than two, amine-cured SCECGE produced a T_g very similar to that of NC514 and thus could be useful in formulating epoxy with renewable cardanol content.

Polymers (Basel, Switzerland) 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, Computed Properties of 1761-71-3.

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

Liu, Haitao published the artcileRobust and flexible transparent protective film fabricated with an ambient-curable hybrid resin, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Journal of Coatings Technology and Research (2021), 18(4), 1065-1073, database is CAplus.

An ambient-curable hybrid resin (ACHR) terminated with trimethoxysilane functional groups, synthesized through a simple ring-opening reaction between 3-glycidyloxypropyltrimethoxysilane (KH560) and 4,4′-methylenebis (cyclohexylamine) (PACM), was applied to the surface of a transparent organic polymer to produce a robust, flexible, and transparent protective hybrid film, moisture cured at room temperature The structure, morphol., and optical, mech., and thermal properties of the obtained hybrid film were evaluated. The hybrid film allowed the transmittance of more than 87% of visible light (at 600 nm), maintaining almost the same high transparency as bare PET film. The unique flexible segments and rigid segments in the inorganic-organic hybrid structure of the film realized superior resistance to bending and scratching. The hybrid film-coated PET demonstrated excellent flexibility, with an extremely low bending radius, illustrated by wrapping around a 1-mm mandrel bar without cracking. In addition, the hybrid film exhibited superior pencil hardness (of 2H) and excellent wear durability, i.e., no scratching after being subjected to 200 abrasion cycles using #0000 steel wool under a 19.6 kPa load. The robust, flexible, and transparent protective film developed here, and its simple and efficient preparation method, should have extensive application prospects.

Journal of Coatings Technology and Research 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, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

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

Zuo, Hanqi published the artcileEffect of structure on the properties of ambient-cured coating films prepared via a Michael addition reaction based on an acetoacetate-modified castor oil prepared by thiol-ene coupling, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Progress in Organic Coatings (2019), 27-33, database is CAplus.

The Michael addition reaction was used to create ambient curable film materials based on an acetoacetate-modified castor oil, and a multifunctional alamine was prepared The thiol-ene coupling reaction could change the proportion of hydroxyl groups in the castor oil, thereby improving the crosslinking d. and mech. properties of the coating films. The acetoacetate-modified castor oil was achieved in two steps. First, the C=C bonds of castor oil were coupled using a thiol-ene coupling reaction, which has a high conversion rate and few byproducts. Second, acetoacetate-modified castor oil was prepared by a transesterification reaction between tert-Bu acetoacetate and modified castor oil. The acetoacetate-modified castor oil was characterized by NMR (NMR), Fourier transform IR spectroscopy (FTIR), gel permeation chromatog. (GPC) and viscosity measurements. Finally, coating films were prepared from the acetoacetate-modified castor oil and 4,4-diaminecyclohexylmethane via a Michael addition reaction at room temperature (25 °C). The mech. properties were noticeably improved compared to those of the unmodified castor oil film. The tensile properties increased from 0.68 MPa to 1.76 MPa, and the glass transition temperature (T_g) increased by approx. 30 °C.

Progress in Organic Coatings 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 C10H9NO4S, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

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