33104-32-4

Upstream product

• 42160-93-0 3-(naphthalen-2-yl)cyclohex-2-en-1-one 
• 626-02-8 3-Iodophenol 
• 591-20-8 3-Bromophenol 
• 32316-92-0 naphthalene-2-boronic acid 
• 667940-23-0 2-(3-bromophenyl)naphthalene 
• 10365-98-7 3-methoxyphenylboronic acid 
• 580-13-2 2-bromonaphthalene 
• 33104-31-3 β-(3-methoxyphenyl)naphthalene 
• 42508-60-1 1-(2-oxopropyl)pyridinium chloride 
• 136539-66-7 3-diethylamino-1-[2]naphthyl-propan-1-one; hydrochloride 
• 87199-18-6 3-hydroxyphenylboronic acid 

Downstream Products

• 933066-91-2 5-naphthalen-2-yl-2,2-diphenyl-2H-chromene 
• 933066-99-0 7-naphthalen-2-yl-2,2-diphenyl-2H-chromene 

Relevant academic research and scientific papers

Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents

An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.

COMPOUNDS AND METHODS FOR TREATING OXALATE-RELATED DISEASES

Disclosed herein are compounds and compositions for modulating glycolate oxidase, useful for treating oxalate-related diseases, such as hyperoxaluria, where modulating glycolate oxidase is expected to be therapeutic to a patent in need thereof. Methods of modulating glycolate oxidase activity in a human or animal subject is also provided.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

An acetatopalladium(II) complex with 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

The Schiff base 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine (HL) and its acetatopalladium(II) complex having the formula [Pd(L)(OAc)] were synthesized. Both HL and [Pd(L)(OAc)] were characterized using elemental analysis and various spectroscopic (infrared, UV–visible, 1H NMR and 13C NMR) and mass spectrometric measurements. The molecular structure of the complex was determined using X-ray crystallographic analysis. In the complex, the pincer-like NNO-donor L? and the monodenate OAc? provide a distorted square-planar N2O2 coordination environment around the metal centre. The physicochemical properties and the spectroscopic features of [Pd(L)(OAc)] are consistent with its molecular structure. The complex was found to be an effective catalyst for the Suzuki–Miyaura cross-coupling reactions of hydroxyaryl halides with arylboronic acids in predominantly aqueous media. The reactions afforded hydroxybiaryl products in good to excellent yields with a wide substrate scope.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

Copper-catalyzed oxidative aromatization of 2-cyclohexen-1-ones to phenols in the presence of catalytic hydrogen bromide under molecular oxygen

Catalytic oxidative aromatization has been achieved using 2-cyclohexen-1-ones to obtain phenol derivatives in the presence of a catalytic amount of copper salt and aqueous HBr under molecular oxygen. The amount of HBr was successfully reduced to a catalytic quantity, and the other additive such as a ligand and an oxidant as well as inert conditions were unnecessary. Various mono-, di-, and trisubstituted phenols with substituents at the desired positions could be synthesized under cheap and simple conditions. An oxidative aromatization/bromination sequence was also demonstrated to obtain bromophenols with excess HBr. The Royal Society of Chemistry 2013.

17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES

The invention relates to the use of non-steroidal 17beta-hydroxysteroid dehydrogenase type 1 inhibitors for the treatment and prophylaxis of hormone-dependent, particularly estrogen-dependent, diseases.The invention further relates to suitable inhibitors and to a method for the production thereof.

Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: Potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases

Human 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) catalyzes the reduction of the weak estrogen estrone (E1) to the highly potent estradiol (E2). This reaction takes place in the target cell where the estrogenic effect is exerted via the estrogen receptor (ER). Estrogens, especially E2, are known to stimulate the proliferation of hormone-dependent diseases. 17β-HSD1 is overexpressed in many breast tumors. Thus, it is an attractive target for the treatment of these diseases. Ligand- and structure-based drug design led to the discovery of novel, selective, and potent inhibitors of 17β-HSD1. Phenyl-substituted bicyclic moieties were synthesized as mimics of the steroidal substrate. Computational methods were used to obtain insight into their interactions with the protein. Compound 5 turned out to be a highly potent inhibitor of 17β-HSD1 showing good selectivity (17β-HSD2, ERα and β), medium cell permeation, reasonable metabolic stability (rat hepatic microsomes), and little inhibition of hepatic CYP enzymes.

Photochromism of arylchromenes: Remarkable modification of absorption properties and lifetimes of o-quinonoid intermediates

(Chemical Equation Presented) A significant π-conjugation in 6- and 7-arylchromenes manifests dramatically in the absorption properties of their photogenerated o-quinonoid intermediates. This in conjunction with facile synthesis via Suzuki coupling may render a myriad of photochromic arylchromenes with wide-ranging spectrokinetic properties readily accessible.

Syntheses of 3-arylphenols from (3-aryl-3-oxopropyl)dialkylammonium chlorides and 1-(2-Oxopropyl)pyridinium chloride

The reactions of (3-aryl-3-oxopropyl)dialkylammonium chlorides 1a-f with 1-(2-oxopropyl)pyridinium chloride (2) and triethylamine gave the 3-arylphenols 3a-f with yields from 43 to 83%.