39716-58-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Pentenoyl chloride is used as a synthetic intermediate for the preparation of D-pro-L-derived cyclic peptides, which are essential in the development of novel drugs with potential applications in the treatment of various diseases.
Used in Chemical Research:
4-Pentenoyl chloride is used as a reagent in the synthesis of 4-pentenoylcobalt tricarbonyl, a complex compound that has potential applications in the field of organometallic chemistry and catalysis.
Used in Biochemistry:
4-Pentenoyl chloride is used as a modifying agent for the preparation of N-4-pentenoyl-L-cysteine methyl ester, which is an important compound in the study of protein structure and function, as well as in the development of new bioactive molecules.

InChI:InChI=1/C5H7ClO/c1-2-3-4-5(6)7/h2H,1,3-4H2

Upstream product

• 591-80-0 pent-4-enoic acid 
• 95091-90-0 N-methoxy-N-methyl-4-pentenamide 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 610-89-9 2-acetyl-pent-4-enoic acid ethyl ester 
• 79-37-8 oxalyl dichloride 
• 1968-40-7 ethyl 4-pentenoate 

Downstream Products

• 1577-22-6 5-hexenoic acid 
• 86164-01-4 pent-4-enoic acid-(2-cyclohexyl-4,6-dinitro-phenyl ester) 
• 2565-39-1 hept-6-en-3-one 
• 930-30-3 cyclopent-2-enone 
• 23088-65-5 pent-4-enoic acid [(4-nitro-phenyl)-thiocarbamoyl]-amide 
• 88046-53-1 2-pent-4-enoylcyclohexanone 
• 124643-73-8 1,7,8,8a-Tetrahydro-(7S^*,8aS^*)-5-cyano-7-phenyl-3-(2H)-indolizinone 
• 90735-74-3 2-(4-pentenoyloxy)cyclohex-2-enone 
• 81819-01-4 2',6'-bis(1,1-dimethylethyl)-4'-methylphenyl 4-pentenoate 
• 77320-44-6 methyl 2-(benzoylamido)-3-oxo-6-heptenoate 
• 145801-83-8 N-(5,5-dimethyl-3-oxocyclohex-1-enyl)-N-hexylpent-4-enamide 
• 145801-84-9 N-benzyl-N-(5,5-dimethyl-3-oxocyclohex-1-enyl)pent-4-enamide 
• 131506-91-7 3-Oxo-2-(triphenyl-λ⁵-phosphanylidene)-hept-6-enoic acid tert-butyl ester 
• 145801-82-7 N-benzyl-N-(3-oxocyclohex-1-enyl)pent-4-enamide 

Relevant academic research and scientific papers

Degenerative xanthate transfer to olefins under visible-light photocatalysis

The degenerative transfer of xanthates to olefins is enabled by the iridium-based photocatalyst [Ir{dF(CF3)ppy}2(dtbbpy)](PF6) under blue LED light irradiation. Detailed mechanistic investigations through kinetics and phot

Oxidative Hydro-, Bromo-, and Chloroheptafluoroisopropylation of Unactivated Alkenes with Heptafluoroisopropyl Silver

Oxidant-induced three-component hydro-, bromo-, and chloroheptafluoroisopropylation of unactivated alkenes are disclosed. In these reactions, the CF(CF3)2 radical was generated from the oxidation of AgCF(CF3)2.

Synthesis, characterization and conducting properties of sulfonated poly and co-polymer of cholesteryl 4-pentenoate with 1-hexene

This manuscript reports the synthesis of the liquid crystalline (LC) monomer cholesteryl 4-pentenoate and its sulfone and co-polysulfone with 1-hexene. The polymers were characterized by IR, 1H-NMR, differential scanning calorimetry and thermogravimetric analysis techniques. The LC phases were observed under a hot stage fitted with a polarizing optical microscope. The elemental analysis for the sulfone group was done by SEM (energy dispersive X-ray analysis) analysis. The amount of elemental sulfur present in polysulfone and co-polysulfone is 4.95 weight (%) and 5.71weight (%), respectively. The molecular weights were determined by Gel Permeation Chromatography, using tetrahydrofuran as the solvent. The number average molecular weight of the polysulfone is 5950 g/mol. The molecular weights of the co-polysulfones were found to be higher than the polysulfone. From I-V characteristics, the breaking voltage for the polymers was computed to be around 5 V. The conductivity of the polysulfone and co-polysulfones increases with increasing temperature.

A short and efficient synthesis of bridgehead mono-and dideuteriated tropinones

Studies of the biosynthesis and degradation of alkaloids of the tropane class require substrates isotopically-labelled at specific positions. To investigate the mechanism of the enzyme reactions involved in the hydroxylation of the bridgehead position(s), compounds deuteriated at this position are needed. An efficient synthesis of 1,5-dideuterio-and racemic 1-deuteriotropinone is described in which high levels of deuterium are incorporated from the corresponding di-and mono-labelled 2,5-dibutoxytetrahydrofuran.

Total synthesis of phenanthroindolizidine alkaloids through an amidyl radical cascade/rearrangement reaction

A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanth

Synthesis and recognition properties of polymers containing embedded binding sites

We report the synthesis and guest affinities of polymers featuring a single recognition site in the middle of the polymer chain. These polymers were synthesized from difunctional initiators based on the 2,6-diacyldiaminopyridine moiety. Binding efficiencies were experimentally determined using a complementary fluorescent guest, N(10)-isopropyl flavin. The effect of polymer length on recognition was explored by the synthesis of 5 PMMA samples ranging from 4K to 25K. Over this range binding constants increased almost 2-fold, from 282 to 522 M-1. Variable temperature fluorescence of bound samples shows a 15% difference in release between polymer samples and model compounds.

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes

A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-α-amino-β-hydroxy and α,β-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.

Electrodimerization ofN-Alkoxyamides for the Synthesis of Hydrazines

An efficient and valuable N-N dimerization reaction ofN-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, anN-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, variousN-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.