83622-41-7

Usage

Uses

Used in Organic Synthesis:
1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,4,5,5-tetramethylis used as a general reagent for the iterative synthesis of asymmetric (secondary) alkyl boronate esters. This allows for the creation of a wide range of chemical compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,4,5,5-tetramethylis used as a key intermediate in the synthesis of various drug molecules. The ability to form asymmetric alkyl boronate esters enables the development of new and innovative medications with improved efficacy and selectivity.
Used in Chemical Research:
1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,4,5,5-tetramethylis also used in chemical research to explore new methods of derivatization and chemical transformations. This helps to expand the understanding of organic chemistry and contributes to the discovery of new synthetic pathways and applications.
Used in Material Science:
In the field of material science, 1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,4,5,5-tetramethylcan be employed in the development of new materials with unique properties. The versatility of this reagent allows for the synthesis of novel polymers, coatings, and other materials with potential applications in various industries.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 62260-98-4 (dichloromethyl)boronic acid 
• 121-43-7 Trimethyl borate 
• 115921-03-4 dichloromethyl boronic acid dimethyl ester 
• 75-09-2 dichloromethane 

Downstream Products

• 83622-42-8 2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 94242-82-7 2-(1-chloro-2-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1242770-50-8 (E)-4,4,5,5-tetramethyl-2-(4-trifluoromethylphenyl-vin-1-yl)-1,3,2-dioxaborolane 
• 1253943-66-6 (E)-4,4,5,5-tetramethyl-2-(3-bromophenyl)ethen-1-yl-1,3,2-dioxaborolane 
• 933986-82-4 (E)-4-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl]phenol 
• 2066512-27-2 2-(diiodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 87100-31-0 2-(chloro(cyclohexyl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Asymmetric Synthesis and Biological Screening of Quinoxaline-Containing Synthetic Lipoxin A4Mimetics (QNX-sLXms)

Failure to resolve inflammation underlies many prevalent pathologies. Recent insights have identified lipid mediators, typified by lipoxins (LXs), as drivers of inflammation resolution, suggesting potential therapeutic benefit. We report the asymmetric preparation of novel quinoxaline-containing synthetic-LXA4-mimetics (QNX-sLXms). Eight novel compounds were screened for their impact on inflammatory responses. Structure-activity relationship (SAR) studies showed that (R)-6 (also referred to as AT-02-CT) was the most efficacious and potent anti-inflammatory compound of those tested. (R)-6 significantly attenuated lipopolysaccharide (LPS)- and tumor-necrosis-factor-α (TNF-α)-induced NF-κB activity in monocytes and vascular smooth muscle cells. The molecular target of (R)-6 was investigated. (R)-6 activated the endogenous LX receptor formyl peptide receptor 2 (ALX/FPR2). The anti-inflammatory properties of (R)-6 were further investigated in vivo in murine models of acute inflammation. Consistent with in vitro observations, (R)-6 attenuated inflammatory responses. These results support the therapeutic potential of the lead QNX-sLXm (R)-6 in the context of novel inflammatory regulators.

Studies on a catalytic version of the Matteson asymmetric homologation reaction

Studies of a catalytic asymmetric version of the Matteson reaction between dichloromethylboronates and organolithium reagents have been undertaken. From several different chiral catalytic systems studied, only one based on a mannitol derivative has given substantial asymmetric induction close to that previously achieved with a bis(oxazoline) derivative and ytterbium triflate. More detailed study of the latter reaction revealed that fresh ytterbium triflate actually reduced the level of asymmetric induction, while "aged"ytterbium triflate, or a fresh sample that had been treated with water, brought about improved induction. The implications of these findings are discussed.

Discovery of LOU064 (Remibrutinib), a Potent and Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase

Bruton's tyrosine kinase (BTK), a cytoplasmic tyrosine kinase, plays a central role in immunity and is considered an attractive target for treating autoimmune diseases. The use of currently marketed covalent BTK inhibitors is limited to oncology indications based on their suboptimal kinase selectivity. We describe the discovery and preclinical profile of LOU064 (remibrutinib, 25), a potent, highly selective covalent BTK inhibitor. LOU064 exhibits an exquisite kinase selectivity due to binding to an inactive conformation of BTK and has the potential for a best-in-class covalent BTK inhibitor for the treatment of autoimmune diseases. It demonstrates potent in vivo target occupancy with an EC90 of 1.6 mg/kg and dose-dependent efficacy in rat collagen-induced arthritis. LOU064 is currently being tested in phase 2 clinical studies for chronic spontaneous urticaria and Sjoegren's syndrome.

Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions

Herein, we report a user-friendly and metal-free UV-A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly

Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

The combination of diiodomethylboronate ester, CrCl2 with TMEDA promoted borylcyclopropanation of unactivated alkenes under mild conditions. Compared with the typical Simmons-Smith cyclopropanation, the current protocol offers the following adv

Diastereoselective borocyclopropanation of allylic ethers using a boromethylzinc carbenoid

A borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities. Several postfunction-alization reactions were also performed to illustrate the versatility of these building blocks.

Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of Its Analogues

Bongkrekic acid (BKA), isolated from the bacterium Burkholderia cocovenenans, is an inhibitor of adenine nucleotide translocator, which inhibits apoptosis, and is thus an important tool for the mechanistic investigation of apoptosis. An efficient total synthesis of BKA has been achieved by employing a three-component convergent strategy based on Kocienski-Julia olefination and Suzuki-Miyaura coupling. It is noteworthy that segment B has been prepared as a new doubly functionalized coupling partner, which contributes to shortening of the number of steps. Torquoselective olefination with an ynolate has also been applied for the efficient construction of an unsaturated ester. Furthermore, it is revealed that 1-methyl-2-azaadamantane N-oxyl is an excellent reagent for final oxidation to afford BKA in high yield. Based on the total synthesis, several BKA analogues were prepared for structure-activity relationship studies, which indicated that the carboxylic acid moieties were essential for the apoptosis inhibitory activity of BKA. More easily available BKA analogues with potent apoptosis inhibitory activity were also developed. Stripped BKA: The highly efficient second-generation total synthesis of bongkrekic acid (BKA), an apoptosis inhibitor, has been developed. The synthesis features a three-component convergent strategy based on a Kocienski-Julia olefination and Suzuki-Miyaura coupling. The structure-activity relationship (SAR) is also examined for the first time (see scheme).

RESVERATROL ANALOGS AND THERAPEUTIC USES THEREOF

Resveratrol analogs and their use to inhibit Kv1.5 channels are provided. The resveratrol analogs are useful in the treatment of atrial arrhythmias, including atrial fibrillation (AF). Exemplary resveratrol analogs are compounds of general Formula (I):

Catalytic Asymmetric Total Syntheses of Quinine and Quinidine

The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity. Copyright