87751-69-7

Usage

Uses

Used in Organic Synthesis:
(±)-trans-1,3-Diphenylallyl acetate is utilized as a key starting material in organic synthesis for the production of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in creating pharmaceuticals, fragrances, and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (±)-trans-1,3-Diphenylallyl acetate serves as an essential intermediate in the synthesis of various drugs. Its unique properties allow for the development of new medicinal compounds with potential therapeutic applications.
Used in Fragrance Industry:
(±)-trans-1,3-Diphenylallyl acetate is employed as a building block for creating unique fragrances and scents. Its chemical structure contributes to the development of novel aroma compounds used in perfumes, cosmetics, and other scented products.
Used in Food and Beverage Industry:
As a flavoring agent and aroma compound, (±)-trans-1,3-Diphenylallyl acetate plays a significant role in enhancing the taste and smell of various food and beverage products. Its incorporation into these products contributes to their overall sensory appeal.
Used in Scientific Research:
(±)-trans-1,3-Diphenylallyl acetate is also an important compound in scientific research, where it is studied for its properties and potential applications in various chemical and biological processes. Researchers explore its reactivity and behavior in different reaction conditions to gain insights into its potential uses and mechanisms.

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 108-24-7 acetic anhydride 
• 100-58-3 phenylmagnesium bromide 
• 108-22-5 Isopropenyl acetate 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 75-36-5 acetyl chloride 
• 4663-33-6 1,3-diphenyl-3-hydroxypropene 
• 108-86-1 bromobenzene 
• 104-55-2 3-phenyl-propenal 
• 591-50-4 iodobenzene 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 136859-93-3 (S)-1',1'-dimethylethyl 2-carbo-1'',1''-dimethylethoxy-3,5-diphenylpent-4-enoate 
• 136859-93-3 (R)-1',1'-dimethylethyl 2-carbo-1'',1''-dimethylethoxy-3,5-diphenylpent-4-enoate 
• 136859-90-0 2-Benzyl-2-((E)-1,3-diphenyl-allyl)-malonic acid dimethyl ester 
• 130866-13-6 (E)-2-(Diethoxy-phosphoryl)-3,5-diphenyl-pent-4-enoic acid ethyl ester 
• 136859-91-1 2-((E)-(R)-1,3-Diphenyl-allyl)-2-(2,2,2-trifluoro-acetylamino)-malonic acid dimethyl ester 
• 136859-91-1 2-((E)-(S)-1,3-Diphenyl-allyl)-2-(2,2,2-trifluoro-acetylamino)-malonic acid dimethyl ester 
• 204578-86-9 ((1E,5E)-hexa-1,5-diene-1,3,4,6-tetrayl)tetrabenzene 
• 3412-44-0 (1E)-1,3-diphenylpropene 
• 121440-78-6 (E)-N-(1,3-diphenyl-1λ³-allyl)-4-methylbenzenesulfonamide 
• 119477-58-6 (E)-(S)-2-Acetyl-3,5-diphenyl-pent-4-enoic acid methyl ester 
• 104637-10-7 (E)-(R)-2-Acetyl-3,5-diphenyl-pent-4-enoic acid methyl ester 
• 121440-87-7 (-)-(R,E)-N-benzyl-(1,3-diphenyl-2-propenyl)amine 
• 121440-87-7 (+)-(S,E)-N-benzyl-(1,3-diphenyl-2-propenyl)amine 

Relevant academic research and scientific papers

Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids

We describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under ne

Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands

The application of palladium complexes of a modular series of axially chiral phosphinamine ligands, the Quinazolinaps, to the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate and methyl dimethyl malonate is described.

Carbamate-based P,O-ligands for asymmetric allylic alkylations

Herein we report the design and successful catalytic application of modified Trost-ligands in asymmetric allylic alkylation (AAA) reactions. A small set of carbamate-monophosphine P,O-ligands has been prepared in a straightforward two-step synthetic procedure. After optimization of the reaction conditions, high catalytic activities and excellent enantioselectivity up to >99% have been attained.

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).

METHODS AND COMPOSITIONS FOR SUBSTITUTED ARYLCYCLOHEPTANE ANALOGS

In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of aryl-cycloheptene scaffolds. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising an aryl-cycloheptene

Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction to Synthesize 8-Quinolylsulfimides

An efficient copper-catalyzed, quinolyl N-directed nitrene transfer reaction to 8-quinolylsulfides was described. A variety of 8-quinolylsulfimides with different functional groups were synthesized in moderate to high yields. The obtained 8-quinolylsulfimides were proved to be promising novel type of bidentate ligands in Pd(II)-catalyzed allylic alkylation.

Spiroketal-Based C2-Symmetric Scaffold For Asymmetric Catalysis

Provided herein is a compound of formula (I): wherein each R is independently selected from the group consisting of C1-8 alkyl, C1-8 heteroalkyl having 1-4 heteroatoms independently selected from N, O, and S, C3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S, C6-10 aryl, and 5-10 membered heteroaryl having 1-4 heteroatoms independently selected from N, O, and S; each X is independently selected from OH, PAr2, P(O)Ar2, OPAr2, C3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S or each X together form O2PNR′2; Ar is C6-10aryl; and each R′ is independently selected from hydrogen and C1-8 alkyl. Also provided are methods of making and using the compound of formula (I).

Preparation and Application of Amino Phosphine Ligands Bearing Spiro[indane-1,2′-pyrrolidine] Backbone

P,Nsp3-bidentate chiral ligands bearing spiro[indane-1,2′-pyrrolidine] backbone were prepared in gram scale for the first time. Pd complexes of these air-stable amino phosphine ligands could catalyze asymmetric allylic substitutions of malonate-, alcohol-, and amine-type nucleophiles in up to 97percent ee and 99percent yield. A crystal structure of [Pd(II)(η3-1,3-diphenylallyl)(ligand)]PF6 indicated possible transition states of the catalytic reactions. These ligands are characteristic of a very rigid backbone, which is simple but highly effective. They rival C2-symmetric bisphosphine, P,Nsp2-bidentate, and P,Nsp3-bidentate ligands in tested allylic substitutions. ?

Ligand's electronegativity controls the sense of enantioselectivity in BIFOP-X palladium-catalyzed allylic alkylations

Palladium-catalyzed allylic alkylations of sodium dimethyl malonate with 1,3-diphenylallyl acetate, employing BIFOP-H (biphenylbisfencholphosphite) and analogue (i.e. BIFOP-X, X = D, Cl, CN, N3) ligands, all yield (S)-enantiomeric products, while alkylations to cyclohexenyl acetate yield the (R)-enantiomeric C-C coupling product (up to 91% yield, 70% ee). The fluoro derivative BIFOP-F however, "switches" the sense of enantioselectivity, yielding the (R)-enantiomer for 1,3-diphenylallyl acetate and the (S)-enantiomer for the cyclohexenyl acetate (up to 92% yield, 67% ee). Computational analyses of transition structures (M06-2X-D3/def2-TZVP//B3LYP-D3(BJ)/def2-SVP) for these Pd-catalyzed allylic alkylations reproduce the experimental preference of BIFOP-H (and analogue BIFOP-X ligands) for (R)- or (S)-enantiomeric products of 1,3-diphenylallyl or cyclohexenyl acetate, respectively. The "F-switch" of the sense of enantioselectivity from BIFOP-H to BIFOP-F is also apparent computationally and is found (NBO-analyses) to originate from lp(Pd) → σ?(P-O) or lp(Pd) → σ?(P-F) hyperconjugations. The higher electronegativity of F vs. H in BIFOP-X hence controls the sense of enantioselectivity of this Pd-catalyzed allylic alkylation.

Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

We present an expedient and economical route to a new spiroketal-based C2-symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in iridium-catalyzed hydroarylations (up to 95 % ee), palladium-catalyzed allylic alkylations (up to 97 % ee), intermolecular palladium-catalyzed Heck couplings (up to 94 % ee), and rhodium-catalyzed dehydroalanine hydrogenation (up to 93 % ee).