1669-54-1

Basic information

• Product Name: 1-(4-methylphenyl)-3-phenylprop-2-en-1-ol
• Synonyms: 1-(4-methylphenyl)-3-phenylprop-2-en-1-ol
• CAS NO: 1669-54-1
• Molecular Weight: 224.302
• Mol File: 1669-54-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-methylphenyl)-3-phenylprop-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methylphenyl)-3-phenylprop-2-en-1-ol(1669-54-1)
• EPA Substance Registry System: 1-(4-methylphenyl)-3-phenylprop-2-en-1-ol(1669-54-1)

Safety Data

• Hazardous Substances Data: 1669-54-1(Hazardous Substances Data)

Upstream product

• 104-55-2 3-phenyl-propenal 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4224-96-8 3-phenyl-1-p-tolylprop-2-en-1-one 
• 122-00-9 para-methylacetophenone 
• 100-52-7 benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 4363-35-3 Dihydroxy-styryl-boran 
• 14371-10-9 (E)-3-phenylpropenal 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 3883-13-4 2,2,2-trichloroethylbenzene 
• 106-38-7 para-bromotoluene 
• 98-86-2 acetophenone 

Downstream Products

• 1669-50-7 1-phenyl-3-(4-tolyl)propan-1-one 
• 62056-37-5 1-methyl-4-[(1E)-3-phenylprop-1-en-1-yl]benzene 
• 62056-38-6 (E)-1-phenyl-3-p-tolylpropene 
• 4224-96-8 3-phenyl-1-p-tolylprop-2-en-1-one 
• 166824-01-7 α-phenyl p-methylcinnamyl alcohol 
• 1352733-26-6 (E)-5-(4-methylstyryl)-1-phenyl-1H-tetrazole 
• 1352733-07-3 (E)-5-styryl-1-(p-tolyl)-1Htetrazole 
• 5012-90-8 4-methylphenyl phenethyl ketone 
• 109296-94-8 3-acetoxy-3-(4-methylphenyl)-1-phenylpropene 
• 1378409-16-5 1,3-dimethyl-4-phenyl-1,2,3-triazolium iodide 

Relevant articles and documents

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

One-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions: Atom-economic synthesis of selenocarbamates and allyl sulfones

In many reactions involving selenosulfonate or thiosulfonate, the sulfone group often leaves in form of benzenesulfinic acid or sodium benzenesulfinate. A one-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions to afford selenocarbamates and allyl sulfone compounds is reported. The sulfinic acid as the first-step side product is converted to the allyl sulfone compound by water promoted reaction with allyl alcohol. Water acts as both an oxygen source of selenocarbamates and as a promoter to drive the second step reaction. The reactions have the advantages of mild conditions, green, environment-friendly, and high atomic economy.

Potassium Base-Promoted Diastereoselective Synthesis of 1,3-Diols from Allylic Alcohols and Aldehydes through a Tandem Allylic-Isomerization/Aldol–Tishchenko Reaction

This study reports the first base-promoted aldol–Tishchenko reactions of allylic alcohols with aldehydes initiated by allylic isomerization. The reaction enables the diastereoselective synthesis of a variety of 1,3-diols with three contiguous stereogenic centers. Unlike commonly reported systems, our method allows the use of readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones.

Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant

The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway

An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles

A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.

Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols

Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.

Selective arylation of aldehydes with di-rhodium(II)/NHC catalysts

Here is described the preparation of four new rhodium(II) complexes bearing axial NHC ligands. The presence of electron-withdrawing bridging ligands resulted in an enhanced reactivity in the arylation of aldehydes with boronic acids when compared with the tetraacetate counterparts. Complex 15 (Rh 2tfa4(IPr)2) proved to be the most active catalyst for this transformation allowing the selective conversion of aromatic, aliphatic and vinyl aldehydes into the respective alcohols in excellent yields. It was demonstrated that the good group tolerance could be further extended to aromatic and conjugated ketones. DFT calculations carried out on this system showed the complementarily of the bridging ligands and axial ligand in these dinuclear complexes. It was also disclosed that Rh(II)/NHC catalytic system can promote the racemization of 1-phenyl ethanol.