57404-77-0

Usage

Uses

Used in Organic Synthesis:
Trans-nonenylboronic acid is utilized as a reagent for the formation of carbon-carbon bonds, specifically through 1,4-addition reactions. Its application is crucial in the synthesis of complex organic molecules, which is vital for the development of new pharmaceuticals and other chemical products.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, trans-nonenylboronic acid serves as a key building block. It is instrumental in the creation of complex organic molecules that can be further developed into potential drug candidates, contributing to the advancement of new therapeutic agents.
Used in Natural Product Synthesis:
Trans-nonenylboronic acid is also employed in the synthesis of natural products. Its unique reactivity and structure facilitate the construction of complex organic frameworks that are often found in naturally occurring compounds, which are of interest for their biological activities and potential applications in medicine and other industries.

InChI:InChI=1/C9H19BO2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9,11-12H,2-7H2,1H3

Upstream product

• 124-13-0 Octanal 
• 59278-44-3 tris(ethylenedioxyboryl)methane 

Downstream Products

• 1067225-25-5 trans-1-(1,3-dimethylphenyl)-1-nonene 
• 1067225-26-6 trans-1-(2-nitrophenyl)-1-nonene 
• 42036-73-7 1-((E)-non-1-enyl)benzene 
• 167858-37-9 1-(4-octyloxyphenyl)-2-[4-(1-trans-nonenyl)-3-fluorophenyl]acetylene 

Relevant academic research and scientific papers

Lithium bis(ethylenedioxyboryl)methide and its reactions with carbonyl compounds and with the chlorotriphenyl derivatives of germanium, tin and lead

Transesterification of tris(dimethoxyboryl)methane, HC[B(OCH3)2]3, with ethylene glycol yielded tris(ethylenedioxyboryl)methane (I), HC(BO2C2H4)3 which with methyllithium in THF at -70°C precipitated lithium bis(ethylenedioxyboryl)methide (II), Li+ HC(BO2C2H4)2-. Reaction of II with Ph3MCl, where M = Ge, Sn, or Pb, gave Ph3MCH(BO2C2H4)2. The analogous 1,3-propanediol ester, Li+HC(BO2C3H6)2-, yielded Ph3MCH(BO2C3H6)2. Treatment of Ph3SnCH(BO2C2H4)2 with MeLi followed by Ph3SnCl gave (Ph3Sn)2CHBO2C2H4, showing that one B and one Sn atom are sufficient to stabilize a carbanion. Reaction of II with aldehydes gave high yields of 1-alkene-1-boronic esters, RCHCHBO2C2H4, with unexpectedly high stereoselectivity, 90-100% trans by NMR analysis. Aqueous work-up of these boronic esters yielded the boronic acids, RCHCHB (OH)2, which crystallized as the pure trans isomers. Ketones react with II in an analogous manner. The reaction with acetophenone was not stereospecific. Functional group compatibility has been demonstrated in condensations of II with 1,3-dichloroacetone, cinnamaldehyde, p-nitrobenzaldehyde, and p-dimethylaminobenzaldehyde. The trans geometry of the major isomer of CH3CHCHBO2C2H4 was proved by B-butylation with butyllithium followed by rearrangement with iodine and base to form cis-2-heptene, a sequence of known stereochemistry, and analogous structure proofs were carried out with cis-CH3CHCHBO2C2H4 and trans-C6H5CHCHBO2C2H4.