57404-76-9

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-HEPTENYLBORONIC ACID is used as a reactant for the Suzuki-Miyaura alkenylation, a widely employed method in the synthesis of biologically active compounds, including pharmaceuticals. This reaction allows for the formation of carbon-carbon bonds, which are crucial in the development of new drugs and therapeutic agents.
Used in Chemical Research:
In the field of chemical research, TRANS-HEPTENYLBORONIC ACID is utilized as a reactant for palladacycle-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes. This process is significant in the synthesis of complex organic molecules with high enantioselectivity, which is essential for the development of chiral drugs and other specialty chemicals.
Used in Organic Synthesis:
TRANS-HEPTENYLBORONIC ACID is employed in double Suzuki couplings, a type of carbon-carbon bond-forming reaction that is widely used in the synthesis of various organic compounds, including natural products and pharmaceuticals. This reaction contributes to the development of new molecules with potential applications in various industries.
Used in Asymmetric Catalysis:
In the realm of asymmetric catalysis, TRANS-HEPTENYLBORONIC ACID is used as a reactant for rhodium-catalyzed asymmetric addition reactions. These reactions are vital in the synthesis of enantiomerically pure compounds, which are crucial for the development of high-performance materials and advanced pharmaceuticals.
Overall, TRANS-HEPTENYLBORONIC ACID plays a significant role in various chemical processes and industries, particularly in the synthesis of complex organic molecules and the development of new drugs and materials.

InChI:InChI=1/C7H15BO2/c1-2-3-4-5-6-7-8(9)10/h6-7,9-10H,2-5H2,1H3/b7-6+

Upstream product

• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 66-25-1 hexanal 
• 5419-55-6 Triisopropyl borate 
• 60595-37-1 (E)-1-iodohept-1-ene 
• 628-71-7 1-Heptyne 
• 98631-59-5 (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole 
• 123507-49-3 (1E)-1-heptenyldibromoborane-dimethylsulfide complex 

Downstream Products

• 208118-05-2 (S)-3-((E)-1-heptenyl)cyclohexanone 
• 608489-15-2 (R)-3-((E)-hept-1-enyl)cyclohexanone 
• 17574-86-6 cis-1-Acetoxyhepten-(1) 
• 169339-75-7 (E)-2-(hept-1'-en-1'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 846606-93-7 4-hydroxy-2-methoxy-6-(2-oxoheptyl)benzoic acid methyl ester 

Relevant academic research and scientific papers

Stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones: Sex pheromone components of the painted apple moth Teia anartoides

All four isomeric 6,8-heneicosadien-11-ones were synthesised using a Suzuki-coupling strategy.

Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds

The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were explored. A highly Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a unique rearrangement, which involved a two-fold ring expansion, to give a fused bicyclic compound or it could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be higher towards alkynes vs. alkenes, with good to moderate regioselectivity towards the terminal carbon. The second compound, a phosphoranyl-triarylborate, was found to have different reactivity as it was highly stable towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure.

Synthesis and biological evaluation of 6,7-disubstituted 4-aminopyrido[2,3-d]pyrimidines as adenosine kinase inhibitors

The synthesis and structure-activity relationship of a series of 6,7-disubstituted 4-aminopyrido[2,3-d]pyrimidines as novel non-nucleoside adenosine kinase inhibitors is described. A variety of substituents, primarily aryl, at the C6 and C7 positions of the pyridopyrimidine core were found to yield analogues that are potent inhibitors of adenosine kinase. In contrast to the 5,7-disubstituted and 5,6,7-trisubstituted pyridopyrimidine series, these analogues exhibited only modest potency to inhibit AK in intact cells.

A photochemical entry to depsides: Synthesis of gustastatin

(Chemical Equation Presented) Herein, we propose a modular and general strategy to construct orcinol-type depsides based on the photolysis of functionalized benzodioxinones (I). Notably, resorcinylic esters are obtained without competing isocoumarin (II) formation, exemplified by the first total synthesis of gustastatin in 10 steps from commercially available trihydroxybenzoic acid.

2-Pyrones possessing antimicrobial and cytotoxic activities

The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile - base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents.

Kinetic Enzymatic Resolution of Cyclopropane Derivatives

The kinetic enzymatic resolution of various cyclopropane derivatives was systematically investigated. The study focused on synthetically useful cyclopropylmethanols (e.g., 18a/j or 19a/j) as well as some rarely investigated cyclopropanols (e.g., 24/25 or 27). The combination of enantioselective catalytic or diastereoselective synthesis of enantiomerically enriched compounds with enzymatic approaches ultimately led to the most convenient route to enantiomerically pure starting materials. Again, this was especially proven for the synthesis of cyclopropanols 18a/j and 19a/j. Key to the successful investigation was to rigorously establish an analytical tool for the analysis of enantiomeric composition of reaction mixtures.

Preparation, properties, and synthetic potentials of novel boronates in a fluorous version (fluorous boronates)

(equation presented) 4a-j R = aryl, alkenyl, alkyl A series of boronic acids were attached to a fluorous tag by esterification. Functional transformations of these boronates together with the fluorous Suzuki coupling reaction illustrated their usefulness in fluorous-phase techniques.

Synthesis of enantiomerically pure cyclopropanes from cyclopropylboronic acids

A general method for the stereocontrolled synthesis of cyclopropanes is described. Various, highly stable, enantiomerically pure alkenylboronic esters 13 have been conveniently synthesized by the direct hydroboration of alkynes 11 using the new chiral 1,3,2-dioxaborolane 15. The high stability was also demonstrated by the selective deprotection of a tert- butyldimethylsilyl protecting group without hydrolyzing the boronic ester. The diastereoselective cyclopropanation of the olefins was achieved by the palladium(II) acetate catalyzed decomposition of diazomethane. This process was optimized giving cyclopropylboronic esters 20/21 in high yield (89-99%) and with good to excellent diastereomeric ratios (up to 95:5). The diastereomers were separated by means of MPLC and their configurations determined by X-ray crystallography (compound 21c), by transformation to known cyclopropanols, and by correlation of NMR data. Treatment with LiAlH4 followed by acidic hydrolysis yielded the enantiomerically pure cyclopropylboronic acid 27 for the first time and allowed the nearly quantitative recovery of the chiral auxiliary 3. Different protocols for the Suzuki coupling reaction of compound 27 were investigated.

Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates

Lithium alkenylborates couple with the monoacetate of 4-cyclopentene-1,3-diol under the nickel catalyst regioselectively and stereospecifically to afford trans 1,3-isomers in good yields. Moreover, an unexpectedly high level of regio-selectivity is observ

Organoboranes. 30. Convenient procedures for the synthesis of alkyl- and alkenylboronic acids and esters

Alkyl- and alkenyldibromoborane-dimethyl sulfide complexes, readily obtained by the hydroboration of alkenes and alkynes with dibromoborane-dimethyl sulfide (HBBr2-SMe2), react with water, giving the corresponding boronic acids, and with alcohols and glycols to give the corresponding esters. Various procedures have been developed for the preparation of boronic esters with primary and secondary alcohols, glycols, and tertiary alcohols. Boronic acids react with primary and secondary alcohols reversibly to form the corresponding esters. The equilibrium may be conveniently displaced in favor of ester by carrying out the reaction in pentane, from which the water component separates. This procedure does away with the necessity of azeotrope distillation of a ternary mixture, extensively used previously for the esterification of boronic acids.