6638-69-3

Usage

Uses

Used in Organic Synthesis:
(3aS,7aS)-2-phenylhexahydro-1,3,2-benzodioxaborole is used as a building block in organic synthesis for the creation of various biologically active compounds. Its versatile structure allows for the development of new molecules with potential applications in different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3aS,7aS)-2-phenylhexahydro-1,3,2-benzodioxaborole is utilized as a key component in the synthesis of pharmaceuticals. Its unique properties contribute to the design and development of new drugs with improved therapeutic effects.
Used in Drug Development:
(3aS,7aS)-2-phenylhexahydro-1,3,2-benzodioxaborole is employed as a reagent in drug development, aiding researchers in the discovery and synthesis of novel therapeutic agents. Its incorporation into drug candidates can enhance their efficacy and selectivity, leading to more effective treatments for various diseases.

Upstream product

• 1792-81-0 cis-1,2-cyclohexane 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 1061181-00-7 (-)-4,5-dimethyl-2-phenyl[1.3.2]dioxaborolane 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1792-81-0 cis-1,2-cyclohexane 
• 4406-77-3 2-Phenyl-1,3,2-dioxaborinane 
• 7462-37-5 (3aR,6aS)-2-phenyl-hexahydrocyclopenta[d][1,3,2]dioxaborole 

Relevant academic research and scientific papers

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Stability of boronic esters - Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane

Relative rates of reaction of the achiral cyclic phenylboronic ester 2-(phenyl)-1,3,2-dioxaborolane with a wide variety of structurally modified diols, have been studied to understand the factors influencing the relative stabilities of boronic esters. It is found that the alkyl substituents on the α-carbons of diols slow down the transesterification, but produce thermodynamically more stable boronic ester. Six-membered boronic esters are thermodynamically more stable than their corresponding five-membered analogs. Amongst cyclic 1,2-diols, cis-1,2-cyclopentanediol displaces ethylene glycol instantaneously whereas trans-1,2-cyclopentanediol is totally unreactive, which suggests that the cis-stereochemistry of the 1,2-diol is a prerequisite for transesterification. Among the 1,5-diols, diethanolamine displaces ethylene glycol quite rapidly forming a more stable bicyclic chelate in which nitrogen is attached to boron by a coordinating bond (as evident by 11B NMR spectroscopy). The oxygen atom of di(ethylene glycol) and the sulfur atom of 2,2′-thiodiethanol do not assist in displacing the ethylene glycol from their boronic esters.

A comparative study of the relative stability of representative chiral and achiral boronic esters employing transesterification

A comparative study of the transesterification of five representative chiral and achiral boronic esters with various structurally modified diols was undertaken to qualitatively understand the factors influencing the relative stability of these boronic esters. Several factors such as chelation, conformation, steric bulk of the substituents, size of the heterocycle, and entropy influence the relative rate of transesterification as well as the stability of the boronic esters. Amongst these boronic esters, pinanediol phenylboronic ester was found to be the most stable boronic ester whereas DIPT boronic ester appeared to be thermodynamically the least stable one. The transesterification with sterically hindered diols was observed to be relatively slow, but afforded thermodynamically more stable boronic esters. Boronic esters derived from cis-cyclopentanediols and the bicyclo[2.2.1]heptane-exo,exo-2,3- diols are relatively more stable. This study not only presents the qualitative picture of relative stability of various boronic esters, but also provides helpful hints regarding the possible recovery of chiral auxiliaries. Many C 2-symmetric chiral auxiliaries, such as 2,3-butanediol, 2,4-pentanediol, DIPT, and cis-cyclohexane-1,2-diol, can be retrieved by simple transesterification of the corresponding boronic esters with commercial inexpensive diols, such as pinacol, 1,3-propanediol, and neopentyl glycol.