287944-06-3

Usage

Uses

Used in Organic Synthesis:
4,4,5,5-Tetramethyl-2-(4-tert-butyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is used as a reagent in Suzuki-Miyaura cross-coupling reactions for forming carbon-carbon bonds. Its steric hindrance and unique structure make it a valuable tool in organic chemistry for constructing complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4,5,5-Tetramethyl-2-(4-tert-butyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is used as a building block for the synthesis of various pharmaceutical compounds. Its ability to form carbon-carbon bonds through Suzuki-Miyaura cross-coupling reactions allows for the creation of diverse and complex drug molecules.
Used in Chemical Research:
4,4,5,5-Tetramethyl-2-(4-tert-butyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane is also used in chemical research as a model compound to study the properties and reactions of boron-containing compounds. Its unique structure and reactivity provide insights into the behavior of similar compounds in various chemical processes.

InChI:InChI=1/C16H29BO2/c1-14(2,3)12-8-10-13(11-9-12)17-18-15(4,5)16(6,7)19-17/h10,12H,8-9,11H2,1-7H3

Upstream product

• 77412-96-5 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 
• 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 
• 41780-53-4 4-tert-butylcyclohexanone tosylhydrazone 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1041002-99-6 (4R,5R)-4,5-bis(2-(4-tert-butylcyclohex-1-enyl)phenyl)-2,2-dimethyl-1,3-dioxolane 
• 850567-91-8 4-tert-butylcyclohex-1-en-1-ylboronic acid 
• 1402704-34-0 C₁₈H₂₁NO₃ 

Relevant academic research and scientific papers

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.

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

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.

Vanilloid receptor ligands and their use in treatments

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache,

1,2-Di(cyclic)substituted benzene compounds

In one aspect, the present invention provides compounds having formula (1) or (100), a salt thereof or a hydrate of the foregoing, which compounds exhibit excellent cell adhesion inhibitory action or cell infiltration inhibitory action, and are useful as therapeutic or prophylactic agents for various inflammatory diseases and autoimmune diseases associated with adhesion and infiltration of leukocytes, such as inflammatory bowel disease (particularly ulcerative colitis or Crohn's disease), irritable bowel syndrome; rheumatoid arthritis, psoriasis, multiple sclerosis, asthma and atopic dermatitis. wherein R10 represents optionally substituted cycloalkyl, etc., R20-23 represent hydrogen, alkyl, alkoxy, etc., R30-32 represent hydrogen, alkyl, oxo, etc., and R40 represents optionally substituted alkyl, etc.

Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: Convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence

The synthesis of 1-alkenylboronic acid pinacol esters via a palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron (pin2B2, pin = Me4C2O2) with 1-alkenyl halides or triflates was carrie

Synthesis of alkenylboronates via palladium-catalyzed borylation of alkenyl triflates (or Iodides) with pinacolborane

Various alkenyl iodides and triflates were borylated with pinacolborane in the presence of Et3N and a catalytic amount of PdCl2(dppf) and AsPh3 to afford the corresponding alkenylboronates in good yields.