13159-16-5

Basic information

• Product Name: 5-phenylpent-4-enyl-1-ol
• Synonyms: 5-phenylpent-4-enyl-1-ol;(E)-5-phenylpent-4-en-1-ol
• CAS NO: 13159-16-5
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• Mol File: 13159-16-5.mol
• Article Data: 87

Chemical Properties

• Boiling Point: 279.3°Cat760mmHg
• Flash Point: 122.5°C
• Appearance: /
• Density: 1.008g/cm³
• Vapor Pressure: 0.00193mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 5-phenylpent-4-enyl-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylpent-4-enyl-1-ol(13159-16-5)
• EPA Substance Registry System: 5-phenylpent-4-enyl-1-ol(13159-16-5)

Safety Data

• Hazardous Substances Data: 13159-16-5(Hazardous Substances Data)

Usage

Description

PPA is the product of peroxidase-catalyzed reduction of PPHP. It can be used as a reference standard for HPLC analysis of peroxidase assays.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 167, 1988 DOI: 10.1016/S0040-4039(00)80043-X

InChI:InChI=1/C11H14O/c12-10-6-2-5-9-11-7-3-1-4-8-11/h1,3-5,7-9,12H,2,6,10H2/b9-5+

Upstream product

• 121746-04-1 ethyl (4Z)-5-phenyl-4-pentenoate 
• 100-52-7 benzaldehyde 
• 70398-43-5 phenyl-tetrahydrofuran-2-yl-malonic acid diethyl ester 
• 137472-45-8 erythro-2-<1-hydroxy(phenyl)methyl>-1-isopropoxy-1-methylsilacyclopentane 
• 6963-10-6 trans-3-chloro-2-phenyltetrahydro-2H-pyran 
• 129454-82-6 2-((E)-5-phenylpent-4-enyloxy)tetrahydro-2H-pyran 
• 211568-52-4 (E)-5-phenylpent-4-en-1-yl acetate 
• 198410-88-7 (Z)-5-dimethylphenylsilyl-5-phenyl-4-penten-1-ol 
• 100-42-5 styrene 
• 821-09-0 n-Pent-4-enyl alcohol 
• 591-50-4 iodobenzene 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 162754-74-7 1-methyl-1-<(Z)-2-phenylethenyl>silacyclobutane 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 10521-91-2 5-phenylpentan-1-ol 
• 16424-50-3 (E)-(5-chloropent-1-en-1-yl)benzene 
• 1129-66-4 5-Cyclohexyl-1-pentanol 
• 32346-57-9 erythro-1-phenyl-1,2,5-pentanetriol 
• 129454-82-6 2-((E)-5-phenylpent-4-enyloxy)tetrahydro-2H-pyran 
• 105364-63-4 (E)-(5-(benzyloxy)pent-1-en-1-yl)benzene 
• 13664-88-5 trans-5-Phenyl-penten-⁽⁴⁾-yl-⁽¹⁾-p-brom-benzolsulfonat 
• 910788-16-8 (E)-(5-iodopent-1-en-1-yl)benzene 
• 503025-52-3 tert-butyldimethyl-[3-(3-phenyloxiranyl)propoxy]silane 
• 503025-53-4 5-(tert-butyldimethyl silyloxy)-1-(4-methoxyphenyl)-1-phenylpentan-2-ol 
• 503025-56-7 5-(4-methoxyphenyl)-4-octyloxy-5-phenylpentanal 
• 503025-60-3 1-(5-iodo-2-octyloxy-1-phenylpentyl)-4-methoxybenzene 
• 503025-62-5 8-(4-methoxyphenyl)-3-methylene-7-octyloxy-8-phenyloctan-2-one 
• 503025-61-4 3-[5-(4-methoxyphenyl)-4-octyloxy-5-phenylpentyl]-pentane-2,4-dione 

Relevant articles and documents

SmI2-H2O-mediated 5-exo/6-exo lactone radical cyclisation cascades

The SmI2-H2O reagent system mediates challenging 5-exo/6-exo lactone radical cascade cyclisations that deliver carbo[5.4.0]bicyclic motifs in a diastereoselective, one-pot process that establish two new carbocyclic rings and four ste

Peroxidase-catalyzed oxidation of 2,4,6-trichlorophenol

2,4,6-Trichlorophenol (TCP) is an environmental contaminant that is toxic, mutagenic, and carcinogenic. We have investigated peroxidase-catalyzed oxidation of TCP as an alternative pathway of TCP bioactivation using horseradish peroxidase (HRP) as a model peroxidase. TCP was shown to function as a reducing substrate for HRP as evidenced by TCP-dependent, HRP-catalyzed reduction of 5-phenyl-4-penten-1-yl hydroperoxide (PPHP) to its corresponding alcohol. In addition, TCP was shown to undergo hydroperoxide (H2O2, ethyl hydroperoxide, or PPHP)-dependent metabolism as evidenced by electronic absorption spectroscopic analysis of reaction mixtures. A single major product was detected by reverse phase HPLC and was identified as 2,6- dichloro-1,4-benzoquinone (2,6-dichloro-2,5-cyclohexadiene-1,4-dione, CAS no. 697-91-6) on the basis of electronic absorption spectroscopy, mass spectrometry, and cochromatography with synthetic standard. In addition, HRP- catalyzed oxidation of TCP yielded EPR-detectable phenoxyl radical intermediates whose EPR spectrum consisted of a 1:2:1 triplet characterized by proton hyperfine coupling constants a(H(3,5)) = 2.35 gauss. Mechanisms for the hydroperoxide-dependent, HRP-catalyzed oxidation of TCP are proposed that are consistent with these results.

Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.