Month: December 2022

Craviso, Gale L. published the artcileCompetitive inhibition of stereospecific opiate binding by local anesthetics in mouse brain, HPLC of Formula: 637-58-1, the publication is Life Sciences (1975), 16(12), 1803-8, database is CAplus and MEDLINE.

Cationic local anesthetics inhibited competitively the stereospecific binding of naltrexone (I) [16590-41-3] and etorphine [14521-96-1] to the mouse brain opiate receptor. In contrast, the inhibition produced by benzocaine [94-09-7], a noncationic local anesthetic, was noncompetitive. Thus, it appears that the cationic group of local anesthetics interacts with a specific anionic binding site on the opiate receptor and that there are certain structural similarities between the receptors for both types of drugs. In addition, several drugs appear to be able to unspecifically modify the pharmacol. effects of opiates and they could be useful tools to further characterize the opiate receptor.

Life Sciences published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, HPLC of Formula: 637-58-1.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Tzschucke, C. Christoph published the artcileArenes to anilines and aryl ethers by sequential iridium-catalyzed borylation and copper-catalyzed coupling, HPLC of Formula: 929626-18-6, the publication is Organic Letters (2007), 9(5), 761-764, database is CAplus and MEDLINE.

N-Alkyl- and N-arylanilines were synthesized from arenes by a two-step sequence of iridium-catalyzed borylation and copper-catalyzed coupling with amines. Diaryl ethers were obtained by a related sequence of arene borylation, followed by coupling with phenols. In particular, 3,5-disubstituted arylamines and aryl ethers were prepared by initiating this sequence with meta-substituted arenes.

Organic Letters published new progress about 929626-18-6. 929626-18-6 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ester,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (3-(Methoxycarbonyl)-5-methylphenyl)boronic acid, and the molecular formula is C6H3BF4O2, HPLC of Formula: 929626-18-6.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Berkowitz, Alex J. published the artcileSynthesis of α-Tropolones through Autoxidation of Dioxole-Fused Cycloheptatrienes, Name: 1,2-Dimethoxybenzene, the publication is Journal of Organic Chemistry (2022), 87(7), 4499-4507, database is CAplus and MEDLINE.

Herein, we describe the formation of tropolones through the autoxidation of Buchner reaction-derived cycloheptatrienes. The reaction is exceptionally simple procedurally, as it involves blowing a stream of compressed air over the cycloheptatriene, and the products can be obtained without any need for chromatog. The chem. works specifically on dioxolane-fused systems or close variants, and substitution patterns are also important. A radical-based mechanistic hypothesis is put forward to explain these results. Finally, we demonstrate the utility of the overall process in the synthesis of amide-appended tropolones and an isomer of stipitatic acid.

Journal of Organic Chemistry published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C8H10O2, Name: 1,2-Dimethoxybenzene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Rio, L. Garcia published the artcileKinetic study of the stability of (NH₂)₂CSSC(NH₂)₂²⁺, Safety of Formamidine disulfide dihydrochloride, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1996), 159-62, database is CAplus.

The kinetics of the decomposition of formamidine disulfide dihydrochloride, (NH₂)₂CSSC(NH₂)₂²⁺ 2Cl^–, in aqueous solution at 25° are general base catalyzed, and rate constants were measured over the pH range 1.91-9.03. Anal. of the data yields ionization constants pK₁ = 5.49, pK₂ = 7.66 and rate constants for deprotonation of the substrate by OH^– and H₂O. For the doubly charged cation, reaction occurs through a small concentration of a reactive tautomer, (HN=)(NH₃⁺)CSSC⁺(NH₂)₂, which is attacked by H₂O. The singly charged cation reacts by parallel pathways involving OH^– and H₂O as attacking bases.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Safety of Formamidine disulfide dihydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Mercier, F. published the artcileThe antispasmodic action of several benzyl derivatives of α-aminopyridine, Application of N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Travaux de la Societe de Pharmacie de Montpellier (1947), 131-4, database is CAplus.

2-(4-Methoxybenzylamino)pyridine (I) (m.p. 120-1°), 2-(3,4-dimethoxybenzylamino)pyridine (II) (m.p. 165°), and 2-(3,4-methylenedioxybenzylamino)pyridine (III) (m.p. 96°) were prepared from the appropriate aldehyde and 2-aminopyridine in the presence of Na (cf. Funke and Fourneau, C.A. 38, 3262.8). At concentrations of 1:12,500 and 1:25,000 in Tyrode solution all 3 compounds depressed the tonus and activity of isolated rabbit intestine preparations Their action in this regard was inferior to that of papaverine. The spasms produced in the isolated intestine by acetylcholine or BaCl₂ were diminished by all 3 compounds (spasmolytic action). The order of effectiveness was: I > III > II. By administration prior to the BaCl₂ the spasm could be suppressed by I, somewhat diminished by III, but unmodified by II. None of the compounds had any effect on the spasm when administered prior to acetylcholine.

Travaux de la Societe de Pharmacie de Montpellier published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Application of N-(4-Methoxybenzyl)pyridin-2-amine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Eggen, MariJean published the artcileTotal Synthesis of Cryptophycin-24 (Arenastatin A) Amenable to Structural Modifications in the C16 Side Chain, Formula: C21H37BO, the publication is Journal of Organic Chemistry (2000), 65(23), 7792-7799, database is CAplus and MEDLINE.

Two efficient protocols for the synthesis of tert-Bu (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-8-phenyl-2,7-octadienoate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of Me 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1′ Me of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analog, tert-Bu (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-Ph compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analog. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lamola, Jairus L. published the artcileEvaluation of P-bridged biaryl phosphine ligands in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, Product Details of C11H10O, the publication is RSC Advances (2021), 11(43), 26883-26891, database is CAplus and MEDLINE.

A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks was described. The rigid biaryl phosphacycles were efficient for synthesis of biaryls ArAr¹ [Ar = 3-MeC₆H₄, 2-naphthyl, 2-thienyl, etc.; Ar¹ = Ph, 2-MeC₆H₄, 2,6-di-MeC₆H₃] via palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl bromides/chlorides with phenylboronic acids. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature

RSC Advances published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Product Details of C11H10O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Toupalas, Georgios published the artcileNon-innocent electrophiles unlock exogenous base-free coupling reactions, Application of 2-Methoxynaphthalene, the publication is Nature Catalysis (2022), 5(4), 324-331, database is CAplus.

Introduced a unifying strategy that eliminates the need for an exogenous base through the use of non-innocent electrophiles (NIE), which were equipped with a masked base that was released in a controlled fashion during the reaction. The universal applicability of this concept were demonstrated by turning multiple, traditionally base-dependent, catalytic reactions into exogenous base-free homogeneous processes. Furthermore, the advantageous features of NIEs were demonstrated in multiple applications, such as in a micromole-scale fluorescence-based assay. This led to the discovery of a Ni-catalyzed deoxygenation reaction of aryl carbamates using isopropanol as a benign reductant. In a broader context, this work provided a conceptual blueprint for the strategic utilization of NIEs in catalysis.

Nature Catalysis published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C8H5F3O3, Application of 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Buchanan, Gerald W. published the artcileCarbon-13 nuclear magnetic resonance studies of ortho-substituted anisoles and diphenyl ethers, Quality Control of 2944-47-0, the publication is Canadian Journal of Chemistry (1974), 52(5), 767-74, database is CAplus.

Carbon-13 NMR chem. shifts for 8 anisoles and 15 diphenyl ethers are reported. para-Carbon shieldings are sensitive to the degree of steric interference to conjugative electron release by the ethereal O atom. An empirical correlation between the para-carbon shifts and the average twist angle of the Ph rings from a reference plane was developed. Satisfactory agreement was found between the angles of twist derived from C-13 chem. shifts and those based on other phys. measurements.

Canadian Journal of Chemistry published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Quality Control of 2944-47-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

McClain, Edward J. published the artcileDesign and implementation of a catalytic electron donor-acceptor complex platform for radical trifluoromethylation and alkylation, Synthetic Route of 93-04-9, the publication is ACS Catalysis (2020), 10(21), 12636-12641, database is CAplus.

Electron donor-acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodol. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated Et isonicotinate N-oxide acceptor that undergo a fast N-O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables regeneration of the donor species, representing a rare example of EDA photochem. in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex-promoted reaction is evidenced by the successful multigram-scale trifluoromethylation of Me N-Boc pyrrole-2-carboxylate in a continuous flow manifold.

ACS Catalysis published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Synthetic Route of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem