55066-45-0

Basic information

• Product Name: 3-methyl-5-phenylpent-1-en-3-ol
• Synonyms: 3-methyl-5-phenylpent-1-en-3-ol;3-Methyl-5-phenyl-1-penten-3-ol;Benzenepropanol, alpha-ethenyl-alpha-methyl-;Einecs 259-460-8
• CAS NO: 55066-45-0
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.25484
• EINECS: 259-460-8
• Mol File: 55066-45-0.mol

Chemical Properties

• Boiling Point: 281.5°C at 760 mmHg
• Flash Point: 117.2°C
• Appearance: /
• Density: 0.974g/cm³
• Vapor Pressure: 0.00169mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 3-methyl-5-phenylpent-1-en-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-5-phenylpent-1-en-3-ol(55066-45-0)
• EPA Substance Registry System: 3-methyl-5-phenylpent-1-en-3-ol(55066-45-0)

Safety Data

• Hazardous Substances Data: 55066-45-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O/c1-3-12(2,13)10-9-11-7-5-4-6-8-11/h3-8,13H,1,9-10H2,2H3

Upstream product

• 75-01-4 chloroethylene 
• 2550-26-7 4-Phenyl-2-butanone 
• 3377-92-2 vinyl pivalate 
• 1082207-38-2 (3-methylpenta-3,4-dien-1-yl)benzene 
• 67-63-0 isopropyl alcohol 
• 1826-67-1 vinyl magnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 1226953-84-9 4-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)butan-2-ol 
• 2344-70-9 1-phenyl-3-butanol 

Downstream Products

• 94118-13-5 (3-methylenepent-4-en-1-yl)benzene 
• 136559-10-9 3-Methyl-5-phenyl-1,3-pentadiene 
• 55066-46-1 3-methyl-5-phenylpent-1-en-3-yl acetate 
• 76803-81-1 2-methyl-2-(2-phenylethyl)but-3-enoic acid 
• 137513-39-4 Acetic acid (E)-4-hydroxy-4-methyl-6-phenyl-hex-2-enyl ester 

Relevant articles and documents

α-C-H borylation of secondary alcohols: Via Ru/Fe relay catalysis: Building a platform for alcoholic C-H/C-O functionalizations

An unprecedented α-C-H borylation of secondary alcohols was successfully achieved and delivered various tertiary α-boryl alcohols via [Ru]/[Fe] relay catalysis. The dehydrogenation catalyst (Ru) and borylation catalyst (Fe) interacted to increase the chemoselectivity. By installing the "platform functional group" Bpin via this α-C-H borylation, several alcoholic α-C-H and C-O bond functionalizations were successfully achieved.

Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters

We describe here the first general asymmetric synthesis of sterically encumbered α,α-disubstituted allylic sulfones via Pd-catalyzed allylic substitution. The design and application of a new and highly efficient phosphoramidite ligand (L10) proved to be crucial, and a wide variety of challenging allylic sulfones featuring quaternary stereocenters could be obtained in good yields and with good to excellent levels of regio- and enantioselectivities under attractive process conditions. The developed methodology employs easily accessible chemical feedstock including racemic allylic precursors and sodium sulfinates. The utility of the method is further demonstrated by the synthesis of the sesquiterpene (?)-Agelasidine A.

Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

Switchable Site-Selective Catalytic Carboxylation of Allylic Alcohols with CO2

A switchable site-selective catalytic carboxylation of allylic alcohols has been developed in which CO2 is used with dual roles, both facilitating C?OH cleavage and as a C1 source. This protocol is characterized by its mild reaction conditions, absence of stoichiometric amounts of organometallic reagents, broad scope, and exquisite regiodivergency which can be modulated by the type of ligand employed.

Asymmetric Synthesis of α,α-Disubstituted Allylic Amines through Palladium-Catalyzed Allylic Substitution

The first asymmetric synthesis of important α,α-disubstituted N-alkyl allyl amine scaffolds through allylic substitution is reported. This approach is based on palladium catalysis and features ample scope with respect to both the allylic precursor and amine reagent, and high asymmetric induction with enantiomeric ratios (e.r.) up to 98.5:1.5. The use of less-reactive anilines is also feasible, providing enantioenriched α,α-disubstituted N-aryl allylic amines.

Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products

Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SNi pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.

Organoselenium-catalyzed, hydroxy-controlled regio- and stereoselective amination of terminal alkenes: Efficient synthesis of 3-amino allylic alcohols

An efficient route to prepare 3-amino allylic alcohols in excellent regio- and stereoselectivity in the presence of bases by orangoselenium catalysis has been developed. In the absence of bases α,β-unsaturated aldehydes were formed in up to 97% yield. Control experiments reveal that the hydroxy group is crucial for the direct amination.

Ligand-controlled regiodivergent Ni-catalyzed reductive carboxylation of allyl esters with CO2

A novel Ni-catalyzed regiodivergent reductive carboxylation of allyl esters with CO2 has been developed. This mild, user-friendly, and operationally simple method is characterized by an exquisite selectivity profile that is dictated by the ligand backbone.

Regioselective synthesis of tert-allylic ethers via gold(l)-catalyzed Lntermolecular hydroalkoxylation of allenes

[Chemical equation presented] A highly regioselective method towards tertiary allylic ethers via gold(l)-catalyzed intermolecular hydroalkoxylation of alienes is disclosed. Preventing subsequent isomerizatlon of the tertiary allylic ether products to primary allylic ethers appears to be the key to achieving high regioselectivities.

Titanocene(II)-promoted cross-coupling of unsaturated compounds

Vinyl pivalate in the presence of the titanocene(II) reagent Cp 2Ti[P(OEt)3]2 reacts both with nonpolar C≡C triple bonds and with polar C=O double bonds, to produce conjugated dienes and allylic alcohols, respectively. Similar alkenylation also takes place when (Z)-alkenyl sulfones are treated with alkynes and carbonyl compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.