7766-48-5

Usage

Uses

Used in Organic Synthesis:
5-iodo-1-pentene is utilized as a reagent in organic synthesis for its ability to participate in nucleophilic substitution and metal-catalyzed cross-coupling reactions. Its distinctive structure and reactivity contribute to its effectiveness in these processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 5-iodo-1-pentene is employed as a key intermediate in the synthesis of various organic compounds, including potential drug candidates. Its unique properties facilitate the creation of new molecules with therapeutic potential.
Used in Chemical Research:
5-iodo-1-pentene is also used in chemical research as a model compound to study the behavior of alkenes and the effects of halogen substitution on reactivity and molecular properties. This helps in understanding the fundamental principles of organic chemistry and contributes to the advancement of the field.

Upstream product

• 928-50-7 5-chloropent-1-ene 
• 16408-62-1 cyclobutylmethyl iodide 
• 19300-54-0 toluene-4-sulfonic acid pent-4-enyl ester 
• 821-09-0 n-Pent-4-enyl alcohol 
• 1119-51-3 bromopentene 

Downstream Products

• 71721-20-5 7-Benzenesulfonyl-7-pent-4-enyl-bicyclo[4.2.0]octa-1,3,5-triene 
• 28239-18-1 Dimethyl-5,5-(penten-4-yl)-2-cyclohexandion-1,3 
• 15775-35-6 2-methyl-1-phenylhept-6-en-1-one 
• 124243-68-1 2-(4-Pentenyl)-4-(phenylthio)-3-sulfolene 
• 88046-50-8 3-ethyoxy-6-(4-pentenyl)-2-cyclohexen-1-one 
• 133124-32-0 Phenylsulfonyle-2 heptene-6-oate de methyle 
• 116453-82-8 3,6-Bis-pent-4-enyloxy-phthalonitrile 
• 144542-64-3 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4'-pentenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 104323-54-8 tert-butyl 3-(4'-pentenyl)-2-oxocyclohexanecarboxylate 
• 88046-48-4 2-(pent-4-en-1-yl)cyclohexane-1,3-dione 
• 73172-45-9 2-Hydroxy-1,2-diphenyl-hept-6-en-1-one 
• 182944-12-3 3-(3,3-Dimethyl-but-1-ynyl)-5,5-dimethyl-2-pent-4-enyl-cyclohex-2-enone 
• 485386-66-1 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-methoxy-5-pent-4-enyloxy-6-vinyl-tetrahydro-pyran 
• 830-13-7 cyclododecanone 

Relevant academic research and scientific papers

Total synthesis of guanacastepene A: A route to enantiomeric control

The goal of the total synthesis of guanacastepene A served as a focus to bring together several chemical inquiries. One involved the synthesis of fused 5,7-hydrazulenones (see structure 20). Another issue had to do with the mechanistic intermediates in re

Photocycloisomerization of Boc-protected 5-alkenyl-2,5-dihydro-1H-pyrrol-2-ones

On irradiation (254 nm), the newly synthesized Boc-protected 5-alkenyl-2,5-dihydro-1H-pyrrol-2-ones 13 undergo regioselective intramolecular [2 + 2] photocycloadditions. While the allyl derivatives 13a-13c afford mainly azatricyclo[3.3.0.02.7]octanones, i.e., crossed cycloadducts, the butenyl- and pentenyl-substituted compounds 13d and 13e isomerize preferentially to straight cycloadducts.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Switching substitution groups on the in-tether chiral centre influences backbone peptides' permeability and target binding affinity

Different substitution groups on the in-tether chiral centre of chirality-induced helical peptides (CIH peptides) showed distinguishable effects on the peptides' cellular uptakes and binding affinities with the estrogen receptor α(ER-α). This study proves that in-tether chiral centres are a valuable modification site for constructing peptide ligands with preferable biophysical properties.

Improved synthesis of unnatural amino acids for peptide stapling

The procedures for the synthesis of various α-alkenyl and alkyne amino acids were systematically optimized in light of enhancing atom economy, reducing hazardous reagent usage, and simplifying workup. By starting with Boc-Pro-OH and coupling with EDCI/DMAP followed by alkylation, chiral auxiliary was synthesized with high yield and enantioselectivity. For alkylation of the chiral complex, tBuONa was found and proved by quantitative calculation to be superior to tBuOK in generating more nucleophilic enolate salt, thereby can significantly enhance yield under room temperature. Final Fmoc protection was also dramatically facilitated in one-pot sequential manner by adding EDTA-2Na as the nickel chelator. Synthesis of α-bisalkenyl amino acid was also accomplished by achiral complex approach with high yield and efficacy. Accordingly, five most commonly used N-Fmoc protected α-alkenyl and alkynyl amino acids were synthesized and characterized.

Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes

We report the first copper-catalyzed regio- and stereoselective borylalkylation of dialkylsubstituted internal alkynes with bis(pinacolato)diboron and alkyl halides. A catalytically generated borylcopper species containing a novel π-accepting N-heterocycl

Stabilized alpha helical peptides and uses thereof

Novel polypeptides and methods of making and using the same are described herein. The polypeptides include cross-linking (“hydrocarbon stapling”) moieties to provide a tether between two amino acid moieties, which constrains the secondary structure of the polypeptide. The polypeptides described herein can be used to treat diseases characterized by excessive or inadequate cellular death.

STITCHED POLYPEPTIDES

The present invention provides inventive stitched polypeptides, pharmaceutical compositions thereof, and methods of making and using inventive stitched polypeptides.

Monosubstituted alkenyl amino acids for peptide "stapling"

Alkenylglycine amino acids were assessed as potential candidates for hydrocarbon stapling and shown to be effective in stapling of the BID BH3 peptide.

HEPATITIS C VIRUS INHIBITORS

The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, esters, or prodrugs thereof: Q-G-A-L-B-W (I) which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the