81658-47-1

Usage

Uses

Used in Organic Chemistry:
(3-hydroxy-2-methylpropyl)triphenylphosphonium bromide is used as a phase transfer catalyst for facilitating the transfer of reactants between immiscible phases in organic chemistry reactions. Its ability to bridge different phases enhances the efficiency and selectivity of various chemical processes.
Used in Anticancer Applications:
In the field of oncology, (3-hydroxy-2-methylpropyl)triphenylphosphonium bromide is studied for its potential as an anti-cancer agent. It has demonstrated the ability to induce mitochondrial membrane depolarization and trigger apoptosis in cancer cells, making it a promising candidate for further research and development in cancer treatment.
Used in Antimicrobial Applications:
(3-hydroxy-2-methylpropyl)triphenylphosphonium bromide has also shown antimicrobial properties, which can be leveraged in biomedical and pharmaceutical applications. Its capacity to inhibit the growth of microorganisms positions it as a valuable component in the development of new antimicrobial agents and treatments.
Used in Biomedical Applications:
Due to its unique chemical structure and properties, (3-hydroxy-2-methylpropyl)triphenylphosphonium bromide finds utility in various biomedical applications. Its potential roles in these fields include enhancing drug delivery systems, improving diagnostic tools, and contributing to the advancement of medical research.

InChI:InChI=1/C22H24OP.BrH/c1-19(17-23)18-24(20-11-5-2-6-12-20,21-13-7-3-8-14-21)22-15-9-4-10-16-22;/h2-16,19,23H,17-18H2,1H3;1H/q+1;/p-1/t19-;/m1./s1

Upstream product

• 60782-65-2 (R)-(-)-3-tert-Butoxy-2-methyl-1-bromopropane 
• 603-35-0 triphenylphosphine 
• 93381-28-3 (R)-3-bromo-2-methyl-1-propanol 

Downstream Products

• 371784-87-1 (Z)-(S)-5-Benzyloxy-2-methyl-pent-3-en-1-ol 
• 479495-43-7 (E)-(S)-4-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-methyl-but-3-en-1-ol 
• 753488-80-1 (25S)-4β,7α-dibenzyloxymethoxy-5α-cholest-23-ene-3α,26-diol 3α-benzoate 
• 950669-47-3 (2S)-6-benzyloxy-2-methylhex-3-en-1-ol 
• 573673-77-5 C₂₄H₄₂O₂ 
• 500701-82-6 (Z)-(S)-5-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-2-methyl-pent-3-en-1-ol 
• 79681-06-4 <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole 
• 79681-06-4 <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole 
• 81802-32-6 (R)-(E)-2-methyl-4-phenylbut-3-en-1-ol 

Relevant academic research and scientific papers

Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans

We describe the design and development of the first catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphorimidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.

Progress towards the decalin portion of (+)-compactin

A new approach to a chiral tetrahydronaphthalene precursor for the decalin portion of (+)-compactin is disclosed. The strategy utilises two key steps: a boron-catalysed diastereoselective annulation reaction to a key dioxaborin ester which was then transf

Trimethylsilyl triflate catalysed Diels-Alder reaction of TMS ethers of conjugated dienols with cyclic enones: Evidence for an endo transition state, and first application to synthesis of enantiopure octalins

The AlCl3 catalysed 'ionic' Diels-Alder (DA) reaction of 6-methyl-2- cyclohexenones with 3,5-hexadien-1-ol in dichloromethane gives a trans-fused octalin hemiacetal with a β-equatorial methyl group and an axial hydroxyl. In contrast, trimethylsilyl triflate (TMSOTf, 5 mol%) at -20 °C in acetonitrile catalyses the DA reaction to give the trans-fused adduct acetal, whose controlled hydrolysis gives the hemiacetal with an α-axial methyl group. The adduct is thereby differentiated from the AlCl3 DA adduct, and may be converted into the latter by treatment with p-toluenesulfonic acid in aqueous THF or by AlCl3 in dichloromethane. In similar fashion, TMSOTf provides full acetal adducts from 2-cyclohexenone, 2-cycloheptenone and methyl vinyl ketone. The optically active enone acetal derived from (1R,2R)- 1,2-diphenyl-1,2-ethanediol and 2-cyclohexenone gives a racemic acetal adduct derived from the TMS ether of hexadienol. The TMS ether of a mixture enriched in the 3E-isomer of (2R,5E)-2-methyl-3,5-heptadien-1-ol in acetonitrile containing TMSOTf (10 mol%) at -20 °C with 6-methyl-2-cyclohexenone gives the trans-fused acetal adduct, hydrolysis which provides the corresponding octalin hemiacetal as a single enantiomer. Similarly, the mixture enriched in the 3E-isomer of (2S, 5E)-2-methyl-3,5-heptadienol TMS ether is converted by way of the octalin acetal into the octalin hemiacetal, enantiomeric with the foregoing product. The reactions are thereby shown to proceed via endo transition states.

Intramolecular Nitrile Oxide Cycloaddition (INOC) Reactions in the Indole Series. 2. Total Synthesis of Racemic and Optically Active Paliclavine and 5-epi-Paliclavine

The first total synthesis of the ergot alkaloid paliclavine and the formal total synthesis of paspaclavine in optically active form are described.