Month: December 2022

Ergueden, Jens Kerim published the artcilePhosphoryl functionalized bishomoallyl alcohols by ring opening of epoxides with lithiated allyldiphenylphosphine oxide, Category: catalysis-chemistry, the publication is Synthesis (1996), 707-710, database is CAplus.

Epoxides are attacked by the lithiated anion of allyldiphenylphosphane oxide in 1,2-dimethoxyethane as solvent in a BF₃.OEt₂ promoted ring opening reaction to afford a mixture of regioisomeric bishomoallyl alcs. (¦Á- and ¦Ã-attack of the nucleophile) in good overall yields. When toluene is used as reaction medium a pronounced preference for ¦Ã-attack of the anion is observed Thus, BF₃.OEt₂ promoted reaction of CH₂:CHCH:P(OLi)Ph₂ with ethyloxirane in DMF gave Ph₂P(O)CH(CH:CH₂)CH₂CHMeOH (diastereomeric mixture) along with Ph₂P(O)CH:CHCH₂CH₂CHMeOH, whereas similar reaction with (tosyloxyethyl)oxirane in PhMe gave Ph₂P(O)CH:CHCH₂CH₂CH(CH₂CH₂OTs)OH.

Synthesis published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Metz, Alexander published the artcileFrom Determinants of RUNX1/ETO Tetramerization to Small-Molecule Protein-Protein Interaction Inhibitors Targeting Acute Myeloid Leukemia, Related Products of catalysis-chemistry, the publication is Journal of Chemical Information and Modeling (2013), 53(9), 2197-2202, database is CAplus and MEDLINE.

We identified the first small-mol. protein-protein interaction inhibitors of RUNX1/ETO tetramerization applying structure-based virtual screening guided by predicted hot spots and pockets in the interface. A 3D similarity screening revealed specific hot spot mimetics, one of which prevents the proliferation of RUNX1/ETO-dependent SKNO-1 cells at low micromolar concentration Using solely a protein-protein complex structure to start with, this strategy can be the first step in any comparable structure-based endeavor to identify protein-protein interaction inhibitors.

Journal of Chemical Information and Modeling published new progress about 5411-14-3. 5411-14-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2,2-(1,2-Phenylenebis(oxy))diacetic acid, and the molecular formula is C10H10O6, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Luitjes, Hendrikus published the artcileN-Lithio-N,N’,N”,N”-tetramethyldiethylenetriamine and N’-lithio-N,N,N”,N”-tetramethyldiethylenetriamine; oxidative coupling of aminomethyllithium derivatives, Safety of N1,N1,N2-Trimethyl-N2-(2-(methylamino)ethyl)ethane-1,2-diamine, the publication is Synthetic Communications (1994), 24(16), 2257-101, database is CAplus.

N-lithio-N,N’,N”,N”-tetramethyldiethylenetriamine (I) is formed from 2,5,8,11-tetramethyl-2,5,8,11-tetraazadodecane (II) or from 2,5,8,11,14,17-hexamethyl-2,5,8,11,14,17-hexaazaoctadecane (III) with n-BuLi or sec-BuLi, resp., its isomer N’-lithio-N,N,N”,N”,-tetramethyldiethylene-triamine (IV) from tris(2-dimethylaminoethyl)amine (V) with n-BuLi. III results from treatment of N-lithiomethyl-N,N’,N”N”-tetramethyldiethylenetriamine (VI) with 1,2-dibromoethane.

Synthetic Communications published new progress about 61877-80-3. 61877-80-3 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is N1,N1,N2-Trimethyl-N2-(2-(methylamino)ethyl)ethane-1,2-diamine, and the molecular formula is C8H21N3, Safety of N1,N1,N2-Trimethyl-N2-(2-(methylamino)ethyl)ethane-1,2-diamine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Sanders, Charles R. II published the artcileOrientational behavior of phosphatidylcholine bilayers in the presence of aromatic amphiphiles and a magnetic field, Safety of 5,9-Diaminobenzo[a]phenoxazin-7-ium acetate, the publication is Biophysical Journal (1993), 64(4), 1069-80, database is CAplus and MEDLINE.

A number of aromatic-containing additives which can influence the orientation of fragments of lipid bilayer membranes by a magnetic field have been investigated. Two properties of these additives prove important: (1) sufficient detergency to facilitate reorganization of bilayer components and (2) sufficient anisotropy in magnetic susceptibility to alter the preferred direction of fragment orientation. Triton X-100 is identified as effective in terms of facilitating magnetic field ordering of bilayer fragments but does not alter the preferred direction of orientation. A combination of the detergent CHAPSO (3-[(3-cholamidopropyl)-dimethylammonio]-1-propane sulfonate) and the aromatic alc. 1-naphthol facilitates both ordering and alters the preferred direction of bilayer orientation. As mixtures of dimyristoylphosphatidylcholine (DMPC) and CHAPSO, which orient with bilayer normals perpendicular to the magnetic field, were titrated with 1-naphthol, the assemblies underwent transitions, first to random orientation, and then to an orientation with bilayer normals parallel to the field. Based on temperature-induced phase transitions and the extent of motional averaging of the ³¹P shielding tensor of the DMPC headgroup, the DMPC in these oriented samples appears to maintain a bilayer morphol. during transitions. The insight provided in this study regarding factors which influence fragment stability and orientation lays the groundwork for the design of improved field-oriented media for spectroscopic investigation of membrane components.

Biophysical Journal published new progress about 10510-54-0. 10510-54-0 belongs to catalysis-chemistry, auxiliary class Other Aromatic Heterocyclic,Salt,Amine,Inhibitor,Inhibitor, name is 5,9-Diaminobenzo[a]phenoxazin-7-ium acetate, and the molecular formula is C18H15N3O3, Safety of 5,9-Diaminobenzo[a]phenoxazin-7-ium acetate.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Krollpfelffer, F. published the artcileRing closures in ¦Ã-arylbutyric acids to derivatives of l-ketotetrahydronaphthalene, Related Products of catalysis-chemistry, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 620-32, database is CAplus.

The ¦Ã-arylbutyric acids were prepared by letting the corresponding ¦Ã-keto acids and 10 parts amalgamated Zn stand at least 2-3 hrs., with frequent shaking, under just enough 30% HCl to cover the Zn and then boiling vigorously 6-10 hrs. Although attempts to convert these acids into 1-keto-1,2,3,4-tetrahydronaphthalene (I) derivatives by direct elimination of H₂O between the side chain and the nucleus by means of concd, H₂SO₄ were not successful in all cases, it may be said in general that their tendency to undergo such a condensation is quite pronounced. PhCH₂CH₂CH₂C0₂H (obtained in 80% yield), heated 3 hrs. on the H₂O bath with 5 parts concentrated H₂SO₄ gives 50% I, b₁₃ 127¡ã. From 15 g. p-MeC₆H₄(CH₂)₃CO₂H (obtained in 80% yield) is obtained 9 g. of the 7-Me derivative of I, m. 32.5-3.5¡ã; semicarbazone, m. 224-5¡ã. The ketone (5 g.), reduced by Clemmensen’s method, gives 2 g. 2-methyl-5,6,7,8-tetrahydronaphthalene, b. 224-6¡ã, and with Br in CS₂ yields the 7-methyl-2-bromo derivative of I, m. 80.5¡ã, which produces severe burns on the skin and 9 g. of which, boiled 1 hr. with 50 g. PhNEt₂, regenerates about 1 g. of the Br-free ketone and yields 2 g. 7-methyl-I-naphthol, b₁₂. 158-9¡ã, m. 109¡ã, couples with diazotized P-O₂NC₆H₄NH₂ in alk. solution to a blue dye changing to red with acids. p- EtC₆H₄COCH₂CH₂CO₂H, obtained in 70 g. yield from 60 g. succinic anhydride and 100 g. PhEt with AlCl₃ in C₆H₆, m. 98-9¡ã. ¦Ã-p-Ethylphenylbutyric acid, m. 69-70¡ã, gives 50-5% of the 7-Et derivative of I, b₁₂ 152-3¡ã, slowly becomes brown-red in the air; semicarbazone, m. 223-5¡ã. Reduction of the ketone gives 2-ethyl-5,6,7,8-tetrahydronaph- thalene, b. 245-6¡ã. 2,4-Me₂C₆H₃COCH₂CH₂CO₂H, m. 111-2¡ã; the Me₂C₆H₃(CH₂)₃– CO₂H, m. 71¡ã, gives 10-5 % of the 5,7-Me₂ derivative of I, m. 49-50¡ã, the small yield being due to sulfonation of the xylylbutyric acid. The ketone, which b₁₄ 180-2¡ã, is obtained in 40% yield from Me₂C₆H₃COCl heated in vacuo at 150¡ã until the evolution of HCl ceases; semicarbazone, m. 234-5¡ã. ar-I,3-Dimethyltetralin (2.5 g. from 5 g. of the ketone with amalgamated Zn and HCl), b. 250-2¡ã. ¦Â-2-Tetroylpropionic acid (60 g. from 50 g. succinic anhydride and 100 g. tetralin with AlCl₃ in C₆H₆), m. 121-2¡ã. ¦Â-2-Tetralyl- butyric acid, m. 49-50¡ã, gives 75% 1-ketooctahydroanthracene (“octhracenone,” Schroeter, C. A. 15, 525), b₁₃ 202¡ã, m. 46-7¡ã; semicarbazone, m. 252-3¡ã; 2-Br derivative, m. 110¡ã, produces severe burns on the skin and with PhNEt₂ in part regenerates the Br-free ketone and in part forms 5,6,7,8-tetrahydro-I-anthrol, m. 124¡ã, becomes brown in the air, couples with diazotized P-O₂NC₆H₄NH₂ to a violet dye which is not fast to acids. ¦Â-¦Á’- Naphthoylisosuccinic acid, from CH₂(CO₂Et)₂ refluxed in C₆H₆ with Na and then with ¦Á-C₁₀H₇COCH₂Br, decomposes 158¡ã, with loss of CO₂, 10 g. giving 5 g. of ¦Â-¦Á’-naphthoylpropionic acid, m. 131-2¡ã. ¦Ã-p-Methoxyphenylbutyric acid, m. 59-60¡ã, gives with H₂SO₄ only an easily soluble SO₃H acid, but vacuum distillation of its chloride gives the 7-MeO derivative of I, m. 60-1¡ã; semicarbazone, m. 222-4¡ã. ¦Â-Benzoyl-¦Á-methylpropionic acid (50 g. from 60 g. pyrotartaric anhydride and AlCl₃ in C₆H₆, m. 139-40¡ã. PhCH₂– CH₂CHMeCO₂H, b₁₅ 174¡ã; anilide, m. 140¡ã. 2-Me derivative of I (2 g. from 5 g. of the above acid), b₁₅ 132¡ã, slowly turns brown in the air; semicarbazone, formed exceedingly slowly (3 days), m. 199-201¡ã. Below are given, resp., t¡ã, d₄^t and n for ¦Á, D, ¦Â and ¦Ã at t¡ã for the derivatives of I: ac-2-Me, 20.9¡ã, 1.0600, 1.54669, 1.55154, 1.56542, 1.57764; 7-Me, 35.0¡ã, 1.0569, 1.55168, 1.55674, 1.57160, 1.58479; 7-Et, 17.2¡ã, 1.0556, 1.55478, 1.55988, 1.57454, 1.58752; 5,7-Me₂, 15.5¡ã, 1.0654, 1.55986, 1.56496, 1.57971, 1.59284. Derivatives of tetrahydronaphthalene: ar-2-Me, 15.1¡ã, 0.9541, 1.53316, 1.53719, 1.54907, 1.55897; ar-2-Et, 17.6¡ã, 0.9499, 1.53072, 1.53474, 1.54627, 1,55594; ar-1,3-Me₂, 21.0¡ã, 0.9589, 1.53683, 1.54094, 1.55287.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Vermesse-Jacquinot, Claude published the artcileSpectrophotometric study of the autoprotolytic reaction of 2-aminoethanol, Recommanded Product: Bis(4-nitrophenyl)amine, the publication is Compt. Rend. (1962), 3679-81, database is CAplus.

The autoprotolytic reaction of 2 aminoethanol (I) (2 NH₂CH₂CH₂OH ? NH₃⁺CH₂CH₂OH + NH₂CH₂CH₂O^–) was studied. The value of pK was determined to be 5.14 at 20¡ã, on the basis of previous measurements (CA 55, 17181e) and of measurements of the optical d. of solutions of 4,4′-dinitrodiphenylamine and 2,4-dinitrodiphenylamine in I at 5800 and 5100 A., resp.

Compt. Rend. published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C15H21BO3, Recommanded Product: Bis(4-nitrophenyl)amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Terrier, Francois published the artcileComparison between acidity functions of KOMe and NaOMe in MeOH, Synthetic Route of 1821-27-8, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1966), 263(6), 476-9, database is CAplus.

The following pK values were determined with indicators in KOMe and NaOMe up to 5.5M, resp.: 2,4-dinitrodiphenylamine, 17.16, 17.16; 4,4′-dinitrodiphenylamine 17.49, 17.49; 2,4-dinitroaniline 18.40, 18.35; 4-nitrodiphenylamine 19.62, 19.24; 2,4-dichloro-6-nitroaniline 19.83, 19.36; 2-nitrodiphenylamine 21.36, 20.37; o-nitroaniline 22.30, 21.45; p-nitroaniline 22.40, 21.67. Different solvations of the ions MeOH₂ + .qMeOH and MeO-.p-MeOH are postulated. Important divergences appear rapidly between the 2 acidity functions in each of 2 media (H_m = pK_a + log c + f[log(MeOH)] and J_m = pK_a + log [A-]/[AH]).

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C7H14N4, Synthetic Route of 1821-27-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Di Terlizzi, Lorenzo published the artcileVisible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones, COA of Formula: C14H14, the publication is Journal of Organic Chemistry (2022), 87(7), 4863-4872, database is CAplus and MEDLINE.

The preparation of sym. (hetero)biaryls via arylazo sulfones was successfully carried out upon visible light irradiation in the presence of PPh₃AuCl as the catalyst. The present protocol led to the efficient synthesis of a wide range of target compounds in an organic-aqueous solvent under photocatalyst-free conditions.

Journal of Organic Chemistry published new progress about 613-33-2. 613-33-2 belongs to catalysis-chemistry, auxiliary class Benzene, name is 4,4′-Dimethyldiphenyl, and the molecular formula is C14H14, COA of Formula: C14H14.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Castelli, Riccardo published the artcileBenzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines, Safety of 2,2′-Dithiodibenzoic acid, the publication is Journal of Medicinal Chemistry (2020), 63(3), 1261-1280, database is CAplus and MEDLINE.

We describe a set of benzisothiazolinone (BTZ) derivatives that are potent inhibitors of monoacylglycerol lipase (MGL), the primary degrading enzyme for the endocannabinoid 2-arachidonoyl-sn-glycerol (2-AG). Structure-activity relationship studies evaluated various substitutions on the nitrogen atom and the benzene ring of the BTZ nucleus. Optimized derivatives with nanomolar potency allowed to investigate the mechanism of MGL inhibition. Site-directed mutagenesis and mass spectrometry experiments showed that BTZs interact in a covalent reversible manner with regulatory cysteines, Cys201 and Cys208, causing a reversible sulfenylation known to modulate MGL activity. Metadynamics simulations revealed that BTZ adducts favor a closed conformation of MGL that occludes substrate recruitment. The BTZ derivative 13 protected neuronal cells from oxidative stimuli and increased 2-AG levels in mouse brain. The results identify Cys201 and Cys208 as key regulators of MGL function, and point to the BTZ scaffold as a useful starting point for the discovery of allosteric MGL inhibitors.

Journal of Medicinal Chemistry published new progress about 119-80-2. 119-80-2 belongs to catalysis-chemistry, auxiliary class sulfides,Carboxylic acid,Benzene, name is 2,2′-Dithiodibenzoic acid, and the molecular formula is C14H10O4S2, Safety of 2,2′-Dithiodibenzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Barber, Joyann S. published the artcileRhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones, Application of O-Pivaloylhydroxylamine trifluoromethanesulfonate, the publication is Organic Letters (2019), 21(14), 5689-5693, database is CAplus and MEDLINE.

Rh-catalyzed C-H functionalization of O-pivaloyl benzhydroxamic acids with propene gas provides access to 4-methyl-substituted dihydroisoquinolones. Good to excellent levels of regioselectivity are achieved using [Cp^tRhCl₂]₂ as a precatalyst under optimized conditions. Thorough examination of aryl/heteroaryl O-pivaloyl hydroxamic acid substrates, ligand effects on C-H site selectivity, alkene scope, and demonstration of scale are discussed within.

Organic Letters published new progress about 1293990-73-4. 1293990-73-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is O-Pivaloylhydroxylamine trifluoromethanesulfonate, and the molecular formula is C6H12F3NO5S, Application of O-Pivaloylhydroxylamine trifluoromethanesulfonate.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia