Month: December 2022

Rahal, Mahmoud published the artcileRapid estimation of vibrational zero-point energies of silicon compounds, Recommanded Product: Triethylsilanol, the publication is Computational & Theoretical Chemistry (2013), 182-187, database is CAplus.

In this paper, we extended the application of our empirical formula for the calculation of vibrational zero-point energies (ZPEs) to silicon compounds The bond contribution of Si-C, Si-H, Si-O, Si-Cl and Si-Si were determined The results obtained for more than 90 chem. systems containing these bonds are in good agreement with the exptl. available values. The estimated zero-point energies were compared with the results obtained by application of the extended empirical formula of Schulmann and Disch and with the scaled values obtained using the semi-empirical method (AM1) and the DFT method (B3LYP/6-31G^*), in all cases with satisfactory results.

Computational & Theoretical Chemistry published new progress about 597-52-4. 597-52-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is Triethylsilanol, and the molecular formula is C6H16OSi, Recommanded Product: Triethylsilanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kelly, Tanya published the artcileA Kinetic and Mechanistic Study of the Reactions of OH Radicals and Cl Atoms with 3,3,3-Trifluoropropanol under Atmospheric Conditions, Synthetic Route of 2240-88-2, the publication is Journal of Physical Chemistry A (2005), 109(2), 347-355, database is CAplus and MEDLINE.

Product distribution studies of the OH radical and Cl atom initiated oxidation of CF₃CH₂CH₂OH in air at 1 atm and 298 ± 5 K have been carried out in laboratory and outdoor atm. simulation chambers in the presence and absence of NO_x. The results show that CF₃CH₂CHO is the only primary product and that the aldehyde is fairly rapidly removed from the system. In the absence of NO_x the major degradation product of CF₃CH₂CHO is CF₃CHO, and the combined yields of the two aldehydes formed from CF₃CH₂CH₂OH are close to unity (0.95 ± 0.05). In the presence of NO_x small amounts of CF₃CH₂C(O)O₂NO₂ were also observed (<15%). At longer reaction times CF₃CHO is removed from the system to give mainly CF₂O. The laser photolysis-laser induced fluorescence technique was used to determine values of k(OH + CF₃CH₂CH₂OH) = (0.89 ± 0.03) × 10^-12 and k(OH + CF₃CH₂CHO) = (2.96 ± 0.04) × 10^-12 cm³ mol.^-1 s^-1. A relative rate method has been employed to measure the rate coefficients k(OH + CF₃CH₂CH₂OH) = (1.08 ± 0.05) × 10^-12, k(OH + C₆F₁₃CH₂CH₂OH) = (0.79 ± 0.08) × 10^-12, k(Cl + CF₃CH₂CH₂OH) = (22.4 ± 0.4) × 10^-12, and k(Cl + CF₃CH₂CHO) = (25.7 ± 0.4) × 10^-12 cm³ mol.^-1 s^-1. The results from this investigation are discussed in terms of the possible importance of emissions of fluorinated alcs. as a source of fluorinated carboxylic acids in the environment.

Journal of Physical Chemistry A published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Synthetic Route of 2240-88-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Faverio, Chiara published the artcileAmmonia-Borane-Mediated Reduction of Nitroalkenes, Safety of 2-Methoxy-4-(2-nitroethyl)phenol, the publication is SynOpen (2020), 4(4), 116-122, database is CAplus.

Ammonia-borane was successfully employed in the reduction of nitroalkenes. A variety of nitrostyrenes and alkyl-substituted nitroalkenes were chemoselectively reduced to the corresponding nitroalkanes, in short reaction time, with an atom-economic, simple exptl. procedure that also worked with α- and β-substituted nitroolefins.

SynOpen published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Safety of 2-Methoxy-4-(2-nitroethyl)phenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Masferrer-Rius, Eduard published the artcileAromatic C-H Hydroxylation Reactions with Hydrogen Peroxide Catalyzed by Bulky Manganese Complexes, Product Details of C9H12O, the publication is Advanced Synthesis & Catalysis (2021), 363(15), 3783-3795, database is CAplus.

The oxidation of aromatic substrates to phenols with H₂O₂ as a benign oxidant remains an ongoing challenge in synthetic chem. Herein, the authors successfully achieved to catalyze aromatic C-H bond oxidations using a series of biol. inspired manganese catalysts in fluorinated alc. solvents. While introduction of bulky substituents into the ligand structure of the catalyst favors aromatic C-H oxidations in alkylbenzenes, oxidation occurs at the benzylic position with ligands bearing electron-rich substituents. Therefore, the nature of the ligand is key in controlling the chemoselectivity of these Mn-catalyzed C-H oxidations Introduction of bulky groups into the ligand prevents catalyst inhibition through phenolate-binding, consequently providing higher catalytic turnover numbers for phenol formation. Furthermore, employing halogenated carboxylic acids in the presence of bulky catalysts provides enhanced catalytic activities, which can be attributed to their low pK_a values that reduces catalyst inhibition by phenolate protonation as well as to their electron-withdrawing character that makes the manganese oxo species a more electrophilic oxidant. Moreover, to the best of the authors’ knowledge, the new system can accomplish the oxidation of alkylbenzenes with the highest yields so far reported for homogeneous arene hydroxylation catalysts. Overall the authors’ data provide a proof-of-concept of how Mn(II)/H₂O₂/RCO₂H oxidation systems are easily tunable by the solvent, carboxylic acid additive, and steric demand of the ligand. The chemo- and site-selectivity patterns of the current system, a negligible KIE, the observation of an NIH-shift, and the effectiveness of using ^tBuOOH as oxidant overall suggest that hydroxylation of aromatic C-H bonds proceeds through a metal-based mechanism, with no significant involvement of hydroxyl radicals, and via an arene oxide intermediate.

Advanced Synthesis & Catalysis published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Product Details of C9H12O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Brown, Herbert C. published the artcileChemical effects of steric strain. VI. The effect of ring size on the rate of solvolysis of the 1-chloro-1-methylcycloalkane, Name: 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1952), 1894-1902, database is CAplus.

cf. C.A. 48, 562d. Cyclic compounds undergoing reaction at a ring atom exhibit striking changes in reactivity with variation in ring size. These differences in chem. behavior are attributed to the changes in internal strain in the cyclic structures which accompany changes in the coördination number of the ring atom undergoing reaction (I-strain). 1-Chloro-1-methylcycloalkanes with C₄ to C₁₁ (inclusive), C₁₃, C₁₅, and C₁₇ rings were synthesized and the rates of solvolysis in 80% aqueous EtOH determined (k₁ at 25°). The rate of solvolysis for 1-chloro-1-methylcyclobutane (I) is relatively slow (0.00224/hr.), much slower than open-chain tertiary chlorides. 1-Chloro-1-methylcyclopentane (II) and -heptane (III) undergo solvolysis at a relatively fast rate (1.32 and 1.15/hr., resp.), whereas the corresponding cyclohexane (IV) derivative is slow (0.0106/hr.). The rates reach a maximum with the 8-membered ring (3.30/hr.) and then decrease to become essentially constant at 0.02-0.03/hr. with rings of 13 or more members. The results are in agreement with the predictions based upon the I-strain concept. Methylcyclopropane (V) was chlorinated photochemically at -20° in an attempt to synthesize 1-chloro-1-methylcyclopropane. The reaction yielded cyclopropylcarbinyl chloride (VI), b₇₃₆ 85.5-5.7°, n²⁰_D 1.4349, d₂₀ 0.981; VI via the Grignard reagent yielded an acid, b₂₀ 90-100, n²⁰_D 1.4350-1.4358; amide, m. 103-4°; p-bromophenacyl ester, m. 59.5-60.5°. VI in solvolysis studies behaved as a typical tertiary halide (0.00067/hr.). Reduction of pentaerythrityl bromide with Zn yielded 85-94% hydrocarbon mixture Methylenecyclobutane (b₇₄₄ 42.0°, n²⁰_D 1.4209) treated with HCl at 0° yielded 89% I, b₇₄₂ 89.5-91.4°, n²⁰_D 1.4310. I (9.2 g.) and 75 cc. water refluxed (the mixture was kept neutral by addition of 0.1N NaOH) and the product extracted with Et₂O yielded 54% 1-methylcyclobutanol, b₇₄₂ 116-18°, n²⁵_D 1.4333. HOCH₂CH₂CHMeOH (VII) and HBr at 100° yielded 67% CH₂BrCH₂CHBrMe (VIII), b₅₀ 87-92°, n²⁰_D 1.5080-1.5089. VII and PBr₃ yielded 77% VIII. VIII and Zn in aqueous EtOH yielded 70-88% V. Cyclopentanone (from adipic acid) with MeMgBr yielded 1-methylcyclopentanol (IX), b₇₄₅ 133-6°, m. 32-4°. IX yielded II, b₁₂₁ 66°, n²⁰_D 1.4467. Cyclohexanone yielded the tertiary alc. (X), b₂₉ 72-3.5°, n²⁰_D 1.4609. X yielded IV, b₁₀₀ 83-4°, n²⁰_D 1.4578. Cycloheptanone (b₇₄₇ 172-4°, n²⁰_D 1.4613) yielded 1-methylcycloheptanol (XI), b₂₀ 82-3.5°, n²⁰_D 1.4960. XI with dry HCl yielded 83% III, b_20.5 77-7.5°, n²⁰_D 1.4710. Cycloöctanone (4.06 g.) in 50 cc. Et₂O added MeMgI (from 14.2 g. MeI in 30 cc. Et₂O and 2.43 g. Mg in 15 cc. Et₂O) during 45 min., the mixture refluxed 4 hrs., titrated with saturated NH₄Cl, and the Et₂O evaporated in vacuo yielded 2 g. 1-methylcyclöctanol (XII), m. 34-6°. Distillation of XII yielded 1-methylcycloöctene (XIII), b₇₄₁ 159-64°, n²⁰_D 1.4710. XIII with HCl at 0° yielded the chloride b₄ 64-5°, n²⁰_D 1.4796. Di-Me azelate (b₁₀ 142-50°, n²⁰_D 1.4350-1.4363) by the method of Prelog, et al. (C.A. 42, 1893g), and Stoll, et al. (C.A. 42, 3741dh), yielded 26% crude acyloin fraction (XIV), b₁₂ 110-24°. XIV with Zn-HCl yielded 61% cyclononanone (XV), b₁₂ 92-6°, n⁴⁰_D 1.4682-1.4696. XV (9.8 g.) added during 2 hrs. to 0.21 mole Me Grignard reagent and the mixture refluxed 6 hrs. yielded 6.42 g. 1-methylcyclohexanol (XVI), m. 51-2°. XVI treated 2 hrs. at room temperature with HCl yielded 1-chloro-1-methylcyclononane. Sebacoin (b_0.1 75-85°, m. 36-7.5°, n⁵⁵_D 1.4788) on reduction yielded 73% ketone fraction (b₁₂ 95-112°), which on fractionation (b₁₂106-9°) m. 22-4°, n³⁰_D 1.4784. 1-Methylcyclodecanol (39% yield) m. 52.5-3.1°, Di-Me hendecanedioate (b₃139-50°, n²⁰_D 1.4379-91) yielded 61% acyloin fraction, b_0.08 88-93°, n⁵⁵_D 1.4803, m. 29-32°, which on reduction yielded 55% ketone fraction, b₁₂ 114-20°, n²⁰_D 1.4811; semicarbazone, m. 200-1°. Cycloundecanone (0.05 mole) and 0.15 mole MeMgI yielded 0.60 g. crystalline product, m. 128.5-9.5°, and 5.92 g. 1-methylcycloundecanol, m. 40-2°. For the larger rings, the ketone, its m.p., the tertiary alc., % yield, and m.p. are: cyclotridecanone, 30°, 1-methylcyclotridecanol, 92, 75.5-6.5°; cyclopentadecanone, 61.5-4.5°, 1-methyl-cyclopentadecanol, 80, 83.5-85°; cycloheptadecanone, 58-60°, 1-methylcycloheptadecanol, 92, 77.5-8.5°. -Am MgCl and EtOAc yielded the tertiary alc., b₂ 84.5-6.5°, n²⁰_D 1.4401; diamylmethylcarbinyl chloride was prepared

Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Name: 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Izquierdo, Inaki published the artcileComparative bioavailability study of triflusal oral solution vs. triflusal capsules in healthy subjects: a single, randomized, two-way cross-over, open-label phase I study, Formula: C8H5F3O3, the publication is Arzneimittel Forschung (2010), 60(1), 36-41, database is CAplus and MEDLINE.

Triflusal (CAS 322-79-2) is an antiplatelet agent that irreversibly acetylates cyclooxygenase isoform 1 (COX-1) and therefore inhibits thromboxane biosynthesis. The main metabolite of triflusal, 2-hydroxy-4-trifluoromethyl benzoic acid (HTB), possesses also antiaggregant activity. Recently a new oral 600 mg (10 mL) solution form of triflusal has been developed. The purpose of this clin. trial was to study the relative bioavailability of the new oral solution of triflusal vs. the capsules formulation, both administered as a single dose. This was a randomized, two-way, cross-over, open-label, single-site phase I clin. trial, in 24 healthy volunteers who received triflusal as 600 mg oral solution and as two 300 mg capsules in a single administration separated by a washout period of at least 17 days. Blood samples were collected and plasma concentrations of HTB were measured. Pharmacokinetic parameters used for bioequivalence assessment included AUC_0-t, AUC_0-inf and C_max. The formulations were considered bioequivalent if the geometric mean ratios of AUC_0-t, AUC_0-inf and C_max were within the predetermined equivalence range (80% to 125%). Tolerability was based on the recording of adverse events (AEs), phys. examination, ECG and laboratory tests. The parameters for bioequivalence, mean [SD] values were as follows: AUC_0-t (μg/h/mL): 3574.08 [628.17] for triflusal oral solution and 3901.78 [698.43] for triflusal capsules; AUC_{0-âˆ?/sub> (μg/h/mL): 4089.21 [842.54] for triflusal oral solution and 4471.33 [905.93] for triflusal capsules; Cmax (μg/mL): 91.24 [12.88] for triflusal oral solution and 88.61 [13.46] for triflusal capsules; Cmax/AUC0-âˆ?/sub> (h^-1): 0.03 (0.00) for triflusal oral solution and 0.02 (0.00) for triflusal capsules. The 90% confidence intervals for the ratio exptl./control by anal. of variance after log transformed AUC0-âˆ?/sub>, AUC0-t, and Cmax were within 80% to 125%. Similar results were found for the data without log transformation. All adverse events were of mild or moderate intensity and all subjects recovered. Nine and 12 subjects reported at least one adverse event during treatment with triflusal oral solution and with triflusal capsules, resp. The most frequently reported adverse events were headache and dizziness. It was concluded that the 600-mg solution of triflusal appeared to be bioequivalent to the reference formulation capsules. Both formulations were well tolerated.}

Arzneimittel Forschung published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Formula: C8H5F3O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gros, Philippe published the artcileFirst activation of sodium amide by polymer-supported alkoxides and amino-alkoxides, HPLC of Formula: 101-98-4, the publication is Reactive & Functional Polymers (2000), 43(1,2), 117-122, database is CAplus.

Polystyrene-supported alkoxides and amino-alkoxides are shown to act as efficient and reusable activating agents of sodium amide. This constitutes an unprecedented example of heterogeneous activation in sodium carbanion chem.

Reactive & Functional Polymers published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, HPLC of Formula: 101-98-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Peiro Cadahia, Jorge published the artcileSynthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis, COA of Formula: C14H21BO3, the publication is Journal of Medicinal Chemistry (2018), 61(8), 3503-3515, database is CAplus and MEDLINE.

A series of novel hydrogen peroxide sensitive prodrugs I (11–13; R = H, Me, F) of methotrexate (MTX) and aminopterin (AMT) were synthesized and evaluated for therapeutic efficacy in mice with collagen induced arthritis (CIA) as a model of chronic rheumatoid arthritis (RA). The prodrug strategy selected is based on ROS-labile 4-methylphenylboronic acid promoieties linked to the drugs via a carbamate linkage or a direct C-N bond. Activation under pathophysiol. concentrations of H₂O₂ proved to be effective, and prodrug candidates were selected in agreement with relevant in vitro physicochem. and pharmacokinetic assays. Selected candidates showed moderate to good solubility, high chem. and enzymic stability, and therapeutic efficacy comparable to the parent drugs in the CIA model. Importantly, the prodrugs displayed the expected safer toxicity profile and increased therapeutic window compared to MTX and AMT while maintaining a comparable therapeutic efficacy, which is highly encouraging for future use in RA patients.

Journal of Medicinal Chemistry published new progress about 1370732-71-0. 1370732-71-0 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester, name is (3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol, and the molecular formula is C14H21BO3, COA of Formula: C14H21BO3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Klein, Victoria G. published the artcileAmide-to-Ester Substitution as a Strategy for Optimizing PROTAC Permeability and Cellular Activity, Application of Pentane-1,5-diol, the publication is Journal of Medicinal Chemistry (2021), 64(24), 18082-18101, database is CAplus and MEDLINE.

Criteria for predicting the druglike properties of “beyond Rule of 5” Proteolysis Targeting Chimeras (PROTAC) degraders are underdeveloped. PROTAC components are often combined via amide couplings due to their reliability. Amides, however, can give rise to poor absorption, distribution, metabolism, and excretion (ADME) properties. We hypothesized that a bioisosteric amide-to-ester substitution could lead to improvements in both physicochem. properties and bioactivity. Using model compounds, bearing either amides or esters, we identify parameters for optimal lipophilicity and permeability. We applied these learnings to design a set of novel amide-to-ester-substituted, VHL-based BET degraders with the goal to increase permeability. Our ester PROTACs retained intracellular stability, were overall more potent degraders than their amide counterparts, and showed an earlier onset of the hook effect. These enhancements were driven by greater cell permeability rather than improvements in ternary complex formation. This largely unexplored amide-to-ester substitution provides a simple strategy to enhance PROTAC permeability and bioactivity and may prove beneficial to other beyond Ro5 mols.

Journal of Medicinal Chemistry published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, Application of Pentane-1,5-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Roy, Niloy published the artcileProbing Host-Guest inclusion complexes of Ambroxol Hydrochloride with α- & β-Cyclodextrins by physicochemical contrivance subsequently optimized by molecular modeling simulations, Recommanded Product: trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride, the publication is Chemical Physics Letters (2020), 137372, database is CAplus.

Herein, we report the inclusion of AMB in cyclodextrins leading to host-guest assemblies. The inclusion complexes comprised of Ambroxol Hydrochloride (AMB) with α-cyclodextrin (αCD) and β-cyclodextrin (βCD) have been confirmed by exptl. (UV-vis titration, FTIR, ESI-MS, ¹NMR, 2D-NMR) and computational studies (mol. docking, mol. mechanics calculation). The mol. docking studies demonstrate a better insight into geometry and inclusion mode of AMB inside αCD as well as βCD cavity. Formation of inclusion complexes with different cyclodextrins causes some structural changes of guest mols. during the encapsulation process confirmed by bond length, dihedral angle changes and dynamic simulations.

Chemical Physics Letters published new progress about 23828-92-4. 23828-92-4 belongs to alcohols-buliding-blocks, auxiliary class Membrane Transporter/Ion Channel,Sodium Channel, name is trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride, and the molecular formula is C13H19Br2ClN2O, Recommanded Product: trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts