36884-28-3

Usage

Uses

5-Phenylpentanal is used in preparation of Dihydropyrans for perfumes.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 3243, 1972 DOI: 10.1021/ja00764a063The Journal of Organic Chemistry, 40, p. 2021, 1975 DOI: 10.1021/jo00902a001Tetrahedron Letters, 30, p. 6629, 1989 DOI: 10.1016/S0040-4039(00)70636-8

Upstream product

• 55089-11-7 2-(4-phenyl-butyl)-4,5-dihydro-thiazole 
• 4119-41-9 1-iodo-3-phenylpropan 
• 36884-27-2 2,3,4,4,6-pentamethyl-5,6-dihydro-4H-[1,3]oxazinium; iodide 
• 7726-45-6 5-phenylvaleronitrile 
• 86088-36-0 2-(3-phenyl-propyl)-oxirane 
• 591-50-4 iodobenzene 
• 821-09-0 n-Pent-4-enyl alcohol 
• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 10521-91-2 5-phenylpentan-1-ol 
• 313058-73-0 4-phenyl-1-(2,5-dioxacyclopentyl)butane 
• 201230-82-2 carbon monoxide 
• 768-56-9 4-Phenylbut-1-ene 
• 201486-62-6 1-Indol-1-yl-5-phenyl-pentan-1-ol 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 126613-22-7 5-Phenylpentanal dimethyl acetal 
• 132777-37-8 1-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-5-phenyl-pentan-1-ol 
• 124211-67-2 2-(4-phenylbutyl)phenyl 
• 63223-29-0 (5-Hydroxy-6-methoxyhexyl)benzol 
• 193550-51-5 t-butyl 7-phenyl-hept-2-enoate 
• 1027368-69-9 2-methyl-7-phenyl-hept-2-enoic acid tert-butyl ester 
• 260050-33-7 5-(4-phenyl-butyl)-4-tosyl-2-oxazoline 
• 260050-21-3 (E)-methyl 7-phenylhept-2-enoate 
• 33046-68-3 (E)-8-Phenyl-3-octen-2-on 
• 2270-20-4 5-Phenylpentanoic acid 
• 821785-90-4 (R)-8-phenyloct-1-en-4-ol 
• 868566-32-9 (R)-6-[(2S,4S)-2,4-dihydroxy-8-phenyloctyl]-5,6-dihydro-2H-pyran-2-one 
• 942292-90-2 (5S,2E)-5-hydroxy-9-phenylnon-2-ene 

Relevant academic research and scientific papers

Novel monoacylglycerol lipase inhibitor as well as preparation method and application thereof

The invention discloses a novel monoacylglycerol lipase inhibitor as well as a preparation method and application thereof. Specifically, the invention provides a compound shown as a formula I, or a pharmaceutically acceptable salt, a stereoisomer, or a deuterated derivative thereof. Experimental results show that the compound provided by the invention can effectively inhibit MAGL activity, can beused for preparing an MAGL inhibitor and preparing medicines for preventing and/or treating diseases (including endometrial cancer, colorectal cancer, liver cancer, breast cancer, ovarian cancer, neurodegenerative diseases and the like) related to abnormal MAGL activity, and has a wide application prospect.

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Method for synthesizing fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound

The invention discloses a method for synthesizing a fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound. The method comprises the following steps: S1, sequentially adding 0.01 mmol (1 mol%) of [Rh(cod)Cl]2, 0.1 mmol of a phosphine ligand(P/Rh=10/1) and 1 mmol of diene into a reaction flask, adding 1 ml of a solvent DMF, putting the reaction flask into a high-pressure reaction kettle, after the reaction is finished, transferring a mixed solution into a 25 mL glass bottle with 200 microliters of n-tridecane as an internal standard by using a rubber head dropper, and detecting; and S2, determining the product yield and the structure through a gas chromatograph and a nuclear magnetic resonance spectrum, wherein the obtained olefin conversion rate is larger than 99%, the aldehyde yield ranges from 61% to 99%, and the regioselectivity of the product aldehyde ranges from 70/30 to 100/0. According to the method disclosed by the invention, the separation and purification steps of aldehyde products are simplified, and the substrate of the dialkene hydroformylation reaction is excellent in universality.

Selective Production of Linear Aldehydes and Alcohols from Alkenes using Formic Acid as Syngas Surrogate

Performing carbonylation without the use of carbon monoxide for high-value-added products is an attractive yet challenging topic in sustainable chemistry. Herein, effective methods for producing linear aldehydes or alcohols selectively with formic acid as both carbon monoxide and hydrogen source have been described. Linear-selective hydroformylation of alkenes proceeds smoothly with up to 88 % yield and >30 regioselectivity in the presence of single Rh catalyst. Strikingly, introducing Ru into the system, the dual Rh/Ru catalysts accomplish efficient and regioselective hydroxymethylation in one pot. The present processes utilizing formic acid as syngas surrogate operate simply under mild condition, which opens a sustainable way for production of linear aldehydes and alcohols without the need for gas cylinders and autoclaves. As formic acid can be readily produced via CO2 hydrogenation, the protocols represent indirect approaches for chemical valorization of CO2.

A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation

Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.

Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of α-hydroxy-α-alkenylsilanes

Acid-catalyzed intramolecular Friedel-Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee). The silyl group attached to the chiral carbon played a crucial role in the chirality transfer.

Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis

The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Radical C(sp2)-H Trifluoromethylation of Aldehydes in Aqueous Solution

The copper-mediated C(sp2)-H trifluoromethylation of aldehydes is described. The reaction of aldehydes with (bpy)Cu(CF3)3, Et3SiH, and K2S2O8 in aqueous acetone at room temperatu

Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors

A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.