444575-79-5

Basic information

• Product Name: Carbonic acid, 1,1-dimethylethyl 1-phenyl-2-propenyl ester
• Synonyms: tert-butyl (1-phenylallyl) carbonate;(+/-)-tert-butyl 1-phenylprop-2-en-1-yl carbonate;tert-butyl (1-phenylallyl)carbonate
• CAS NO: 444575-79-5
• Molecular Formula: C14H18O3
• Molecular Weight: 234.295
• Mol File: 444575-79-5.mol

Chemical Properties

• Boiling Point: 295.4±29.0 °C(Predicted)
• Density: 1.031±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Carbonic acid, 1,1-dimethylethyl 1-phenyl-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid, 1,1-dimethylethyl 1-phenyl-2-propenyl ester(444575-79-5)
• EPA Substance Registry System: Carbonic acid, 1,1-dimethylethyl 1-phenyl-2-propenyl ester(444575-79-5)

Safety Data

• Hazardous Substances Data: 444575-79-5(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 100-52-7 benzaldehyde 

Downstream Products

• 1476-07-9 (E)-(3-ethoxy-1-propen-1-yl)benzene 
• 861216-68-4 N'-(1-phenyl-allyl)-hydrazinecarboxylic acid t-butyl ester 
• 119793-72-5 (E)-2-(3-phenyl-allyl) malonic acid dimethyl ester 
• 87802-78-6 dimethyl 2-(1-phenylallyl)malonate 
• 34591-24-7 (E)-2-(3-phenyl-2-propen-1-yl)-4-methylphenol 
• 69299-31-6 (E)-4-cinnamyl-2,6-dimethylphenol 
• 189562-31-0 1,4-dimethyl-2-[(2E)-3-phenylprop-2-en-1-yl]benzene 
• 149045-39-6 1-methoxy-2-[(2E)-3-phenyl-2-propen-1-yl]benzene 
• 20442-73-3 (1E)-3-(4-methoxyphenyl)-1-phenylpropene 
• 149045-33-0 (E)-1-(3-phenyl-2-propen-1-yl)naphthalen-2-ol 

Relevant articles and documents

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

F- Nucleophilic-Addition-Induced Allylic Alkylation

Herein we present a novel strategy based on palladium-catalyzed allylic alkylation by taking advantage of the nucleophilic addition of external fluoride onto gem-difluoroalkenes as the initiation step. The merit of this protocol is highly appealing, as it enables a formal allylation of trifluoroethylarene derivatives through the in situ generation of β-trifluorocarbanions, which otherwise are deemed to be problematic in deprotonative allylation. Furthermore, this strategy distinguishes itself by high modularity, operational simplicity, and wide substrate scope with respect to allyl carbonates, giving rise to a broad array of homoallyltrifluoromethane derivatives, which otherwise would not be easily obtained using existing synthetic methods.

Formaldehyde N, N-dialkylhydrazones as neutral formyl anion equivalents in iridium-catalyzed asymmetric allylic substitution

The use of formaldehyde N,N-dialkylhydrazones as neutral C1-nucleophiles in the iridium-catalyzed substitution of allylic carbonates is described for two processes. Kinetic resolution or, alternatively, stereospecific substitution affords configurationally stable α,α-disubstituted aldehyde hydrazones in high enantiomeric excess and yield. This umpolung approach allows for the construction of optically active allylic nitriles and dithiolanes as well as branched α-aryl aldehydes. A catalyst-controlled reaction with Enders' chiral hydrazone derivatives followed by diastereoselective nucleophilic addition to the hydrazone products constitutes a two-step stereodivergent synthesis of chiral amines.

Direct palladium-catalyzed intermolecular allylation of highly electron-deficient polyfluoroarenes

A simple operation: The use of readily available PPh3, high reaction efficiency, and good stereo- and regioselectivity provided useful and operationally simple access to polyfluoroarylated derivatives through the title transformation (see schem

Pd-catalyzed enantioselective allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of

Synthesis of enantiopure 1-arylprop-2-en-1-ols and their tert-butyl carbonates

(Chemical Equation Presented) Enantiomerically pure 1-arylpropenols 8 have been prepared by resolution of the corresponding racemates, using the lipase formulation Novozyme 435. Deprotonation of the latter alcohols with n-BuLi, followed by derivatization with (t- BuO)2CO, afforded the corresponding carbonates 5. Optimization of the process is presented.

Iridium-catalyzed selective N-allylation of hydrazines

A highly chemo- and regioselective iridium-catalyzed allylic amination is described. The reaction of various hydrazones and hydrazides with allylic carbonates proceeds at ambient temperature in the presence of an [Ir(COD)Cl]2/pyridine catalyst,

General method for the palladium-catalyzed allylation of aliphatic alcohols

A palladium catalysis-mediated approach to coupling aliphatic alcohols with allyl carbonates has been developed. The method allows for the allylation of primary, secondary, and tertiary alcohols efficiently under mild conditions. Limitations were explored as well as the asymmetric application of the chemistry. Regiochemical and olefin geometry was controlled in the coupling of unsymmetrical allylating agents. Transient allyl carbonates were observed in the coupling, which comprised the trans-carboxylation of the allyl-carbonate with the requisite alcohol.