7070-85-1

Upstream product

• 107-21-1 ethylene glycol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 80459-46-7 3-formylphenyl 4-methylbenzenesulfonate 
• 17789-14-9 3-(1,3-dioxolan-2-yl)-phenylbromide 
• 1198597-52-2 C₁₈H₃₀O₃Si 

Downstream Products

• 1196475-04-3 2-bromo-4-(3-[1,3]dioxolan-2-yl-phenoxy)-benzaldehyde 
• 135879-40-2 3,3'-oxybis(benzaldehyde) 
• 906673-24-3 AN₂₇₂₈ 
• 1426224-18-1 C₁₈H₂₀BNO₄*ClH 
• 1426224-14-7 C₁₄H₁₁BO₄ 
• 1196473-84-3 (1-hydroxy-6-(3-morpholin-4-ylmethyl-phenoxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid hydrochloride salt 
• 1196475-02-1 4-[3-(3-carboxymethyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1196475-07-6 (1-hydroxy-6-(3-morpholin-4-ylmethyl-phenoxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 
• 1196475-06-5 (6-(3-[1,3]dioxolan-2-yl-phenoxy)-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 
• 1196475-00-9 [6-(3-formyl-phenoxy)-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester 
• 1196474-98-2 4-[3-(3-ethoxycarbonylmethyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1196473-82-1 (1-hydroxy-6-(3-piperazin-1-ylmethyl-phenoxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 
• 1225034-49-0 (1-hydroxy-6-{3-[(2-methoxy-ethylamino)-methyl]-phenoxy}-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 
• 1196473-83-2 (1-hydroxy-6-{3-[(2-methoxy-ethylamino)-methyl]-phenoxy}-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 

Relevant academic research and scientific papers

Preparation method of crisaborole key intermediate

The invention discloses a method for preparing a crisaborole key intermediate with a structure as shown in a formula I. A synthetic route of the method is as shown in the specification, and the method specifically comprises the following steps: (1) reacting m-hydroxyl benzaldehyde-glycol acetal (II) with an iodine source in the presence of a catalyst to generate an iodinated product III; (2) in the presence of alkali, condensing III and a compound IV to generate V; and (3) in an inert gas atmosphere, carrying out a Miyaura boronation reaction between the compound V and the compound IV under the action of a catalyst to generate a compound VII, which does not need to be further purified, and removing the protection group under the action of acid to obtain a compound I, namely the crisaborole key intermediate. The method has the characteristics of cheap and easily available raw materials, low EHS risk of the used reagent and the synthesis process, simple and convenient separation and purification operation, suitability for industrial production and the like.

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.

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.

Synthesis of Tetranuclear Palladium(II) Complexes and Their Catalytic Activity for Cross-Coupling Reactions

We have developed a short and simple synthesis of tetranuclear palladium(II) complexes that have been structurally confirmed by X-ray analysis. These complexes were formed in about 30 % overall yield by spontaneous metalation of dimethylaminoarene derivatives and exhibit a high stability. We have studied the utility of the tetranuclear palladium(II) complexes as precatalysts for Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions. Our novel complexes show excellent catalytic activities with high turnover numbers (TON) and high turnover frequencies (TOF) (e.g., for the Suzuki–Miyaura reaction: TON up to 538000 and TOF up to 23400 h?1 at room temperature).

Mesoporous sulfated zirconia mediated acetalization reactions

A novel, convenient, one step synthetic procedure for the synthesis of mesoporous sulfated zirconia (m-SZ) using zirconium carbonate complex and its use as solid acid catalyst for the acetalization of different carbonyl compound is reported. The high specific BET surface area (234 m2 g -1) of m-SZ is achieved after the removal of the surfactant (cetyltrymethylammonium bromide, CTAB) through calcination at 550 °C for 6 h. Microscopic analysis indicated the presence of spherical particles with worm like pores. DRIFT (diffuse reflectance FTIR) of pyridine adsorbed m-SZ and NH3-TPD (temperature programmed desorption) analysis suggested the presence of appreciable amount of Bro?nsted acid sites. The synthesized m-SZ showed high catalytic activity towards protection of carbonyl compounds through acetal/ketal formation. For the open ketal (from cyclohexanone and methanol) 97% conversion with 100% selectivity was obtained in 1 h at room temperature under solvent free condition. The catalyst can be easily recycled after separation from the reaction system without considerable loss in catalytic activity.

BORON-CONTAINING SMALL MOLECULES

This invention relates to, among other items, 6-substituted benzoxaborole compounds and their use for treating bacterial infections.

[Hmim]3PW12O40: A high-efficient and green catalyst for the acetalization of carbonyl compounds

[Hmim]3PW12O40 was developed and used in the acetalization of carbonyl compounds in excellent yields. The ionic liquid-heteropoly acid hybrid compound and reaction medium formed temperature-dependent phase-separation system with the ease of product as well as catalyst separation. The catalyst was recycled more than 10 times without any apparent loss of catalytic activity.

Practical, environment-benign and atom economic KOAc-catalysed deprotection of aryl TIPS ethers under mild fluoride-free conditions

A KOAc-catalysed, fluoride-free protocol not only effects chemoselective deprotection of phenolic TIPS ethers without affecting acetal, ketal, carbamate, O-acetyl and aliphatic silyl ethers, but also improves its atom economy by recycling the silanol byproduct.

Co-existence of α-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development

Liver X receptors (LXR), which were originally reported as oxysterol-activated nuclear receptors, were recently found to recognize glucose as a physiological ligand. On this basis, we have already developed novel LXR antagonists based upon α-glucosidase i

An efficient procedure for the preparation of cyclic ketals and thioketals catalyzed by zirconium sulfophenyl phosphonate

A convenient method for the preparation of cyclic ketals and thioketals using zirconium sulfophenyl phosphonate as catalyst is described.