287944-05-2

Usage

Uses

Used in Organic Chemistry:
4,4,5,5-Tetramethyl-2-(4-phenyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is used as a reagent in organic chemistry for a variety of synthetic reactions. Its unique structure allows it to participate in palladium-catalyzed cross-coupling reactions and Suzuki-Miyaura coupling reactions, which are essential for the formation of new carbon-carbon and carbon-heteroatom bonds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4,4,5,5-Tetramethyl-2-(4-phenyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is employed as a key intermediate in the synthesis of various drugs. Its ability to form stable intermediates in cross-coupling reactions makes it a valuable component in the development of new pharmaceutical compounds.
Used in Agrochemicals:
4,4,5,5-Tetramethyl-2-(4-phenyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is also utilized in the agrochemical sector for the synthesis of various agrochemicals. Its role in cross-coupling reactions aids in the production of compounds with potential applications in crop protection and pest control.
Used in Materials Science:
In the field of materials science, 4,4,5,5-Tetramethyl-2-(4-phenyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is employed in the synthesis of advanced materials with unique properties. Its involvement in cross-coupling reactions contributes to the development of new materials with potential applications in various industries, such as electronics, energy, and nanotechnology.
Safety Precautions:
It is crucial to handle 4,4,5,5-Tetramethyl-2-(4-phenyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane with care, as it can be hazardous if not used properly. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, should be followed to minimize the risk of exposure and potential health hazards.

InChI:InChI=1/C18H25BO2/c1-17(2)18(3,4)21-19(20-17)16-12-10-15(11-13-16)14-8-6-5-7-9-14/h5-9,12,15H,10-11,13H2,1-4H3

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 86724-17-6 4-methyl-N’-(4-phenylcyclohexylidene)benzenesulfono hydrazide 
• 73183-34-3 bis(pinacol)diborane 
• 25163-93-3 8-phenyl-1,4-dioxaspiro[4,5]decane 
• 724707-89-5 4-phenylcyclohex-3-en-1-one ethylene glycol ketal 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 170011-47-9 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 122948-47-4 4-phenylcyclohex-1-enyl trifluoromethanesulfonate 

Downstream Products

• 1041003-01-3 (4R,5R)-2,2-dimethyl-4,5-bis(2-(4-phenylcyclohex-1-enyl)phenyl)-1,3-dioxolane 
• 1402704-13-5 4-phenyl-1-cyclohexen-1-ylboronic acid 
• 1400901-95-2 (E)-5-benzyl-6-(4-phenylcyclohexyl)-1H-pyrimidine-2,4-dione 
• 1400902-32-0 (Z)-5-benzyl-6-(4-phenylcyclohexyl)-1H-pyrimidine-2,4-dione 
• 1400902-26-2 5-benzyl-6-(4-phenylcyclohex-1-enyl)-1H-pyrimidine-2,4-dione 
• 143287-94-9 1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-carboxylic acid 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents to generate alkenyl boronic esters

An efficient approach for the synthesis of alkenyl boronic esters through the copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents is reported. This method is distinguished by its mild conditions and short reaction time of less than

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Copper(i)-catalysed regio- and diastereoselective intramolecular alkylboration of terminal allenes: via allylcopper(i) isomerization

We report the first copper(i)-catalysed intramolecular alkylboration of terminal allenes with an alkyl halide moiety. The reaction provides alkenylboronates bearing a four-membered ring structure with high regio- and diastereocontrol. A possible reaction mechanism is proposed, involving the facile isomerization of an allylcopper(i) intermediate. A DFT study explains the experimental regio- and diastereoselectivity.

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.

PYRIMIDINE CYCLOHEXYL GLUCOCORTICOID RECEPTOR MODULATORS

The present invention provides a class of pyrimidinedione cyclohexyl compounds and methods of using these compounds as glucocorticoid receptor modulators

Discovery of a novel non-steroidal GR antagonist with in vivo efficacy in the olanzapine-induced weight gain model in the rat

We report the optimization of a series of non-steroidal GR antagonists that led to the identification of compound 7. This compound is efficacious when dosed orally in an olanzapine-induced weight gain model in rats.

Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol·SnCl4 complexes. Optimization, substrate scope and mechanistic investigations

We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl 4 under Yamamoto's concept of Lewis acid assisted Bronsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic aldehydes are obtained in excellent yields with up to 98:2 er. This combined acid manifold is also efficient in catalyzing the diastereo- and enantioselective crotylboration of aldehydes, thus providing the propionate units in >95:5 dr and up to 98:2 er. The X-ray crystal structure of the optimal diol·SnCl4 complex, Vivol (4m)·SnCl 4, unambiguously shows the Bronsted acidic character of this LBA catalyst and its highly dissymmetrical environment. Further controls have ruled out a possible boron transesterification mechanism with the chiral diol and point to LBA catalyst-derived activation of the pinacol allylic boronates 1. Due to slow dissociation of the diol·SnCl4 complex, a small excess of diol is required in order to suppress a competing racemic cycle catalyzed by free SnCl4.

Convenient preparation of cycloalkenyl boronic acid pinacol esters

A practical method for the preparation of cycloalkenyl boronic acid pinacol esters is described. These important synthetic intermediates are typically made using more expensive methods like transition metal-catalyzed borylation of alkenyl halides or trifl