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**2,4-Pentanedione, 3-(1-phenyl-2-propenyl)-** (also known as 3-cinnamyl-2,4-pentanedione) is a branched allylation product derived from the rhodium-catalyzed reaction of acetylacetone with allylic carbonates or internal alkynes. It features a sterically congested structure due to the 1-phenyl-2-propenyl (cinnamyl) group attached to the central carbon of the 2,4-pentanedione framework. 2,4-Pentanedione, 3-(1-phenyl-2-propenyl)- is selectively formed through rhodium-mediated processes, including allylic alkylation or regioselective addition, where rhodium intermediates (e.g., allylrhodium or Rh-H species) play a key role in controlling the branch selectivity. The retro-allylic alkylation pathway may also influence its formation under certain conditions.

113984-53-5

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113984-53-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 113984-53-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,3,9,8 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 113984-53:
(8*1)+(7*1)+(6*3)+(5*9)+(4*8)+(3*4)+(2*5)+(1*3)=135
135 % 10 = 5
So 113984-53-5 is a valid CAS Registry Number.

113984-53-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(1-phenyl-allyl)-pentane-2,4-dione

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:113984-53-5 SDS

113984-53-5Downstream Products

113984-53-5Relevant academic research and scientific papers

Branch selective allylation of acetylacetone catalyzed by Water-soluble rhodium complex catalyst

Komine, Nobuyuki,Ishiguro, Kohtaro,Kanai, Sachiyo,Hirano, Masafumi,Komiya, Sanshiro

, p. 1927 - 1930 (2011)

[RhCl(1,5-cod)]2/PTA is highly active branch-selective catalyst for C-allylation of acetylacetone by allylic carbonates in water/ethyl acetate biphasic system, where either crotyl or 1-methylallyl carbonates gives sterically congested branched allylation product, suggesting formation of a common allylrhodium intermediate.

Rhodium/Lewis Acid Catalyzed Regioselective Addition of 1,3-Dicarbonyl Compounds to Internal Alkynes

Zheng, Wei-Feng,Xu, Qiu-Jing,Kang, Qiang

, p. 2323 - 2330 (2017)

Herein we describe an efficient protocol for the regioselective addition of 1,3-dicarbonyl compounds to internal alkynes catalyzed by rhodium/Lewis acid catalysts. The corresponding branched/linear allylic alkylation products could be selectively obtained in good yields. Rh-H species were considered to be generated by direct C-H oxidative addition of 1,3-dicarbonyl compounds with rhodium catalyst with the assistance of Lewis acid. Moreover, a retro-allylic alkylation process was observed in this transformation.

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

Bao, Can-Can,Zheng, Dong-Song,Zhang, Xiao,You, Shu-Li

, p. 4763 - 4772 (2019/01/04)

N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,

New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions

Gürbüz, Nevin,Demir, Serpil,?zdemir, Ismail,Cetinkaya, Bekir,Bruneau, Christian

experimental part, p. 1346 - 1351 (2010/04/02)

New tetraimidazolinium and tetrabenzimidazolium salts have been prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce new ruthenium catalysts that

Efficient metal-catalyzed direct benzylation and allylic alkylation of 2,4-pentanediones

Rueping, Magnus,Nachtsheim, Boris J.,Kuenkel, Alexander

, p. 825 - 828 (2007/10/03)

(Chemical Equation Presented) A highly effective metal-catalyzed benzylation and allylic alkylation of 2,4-pentanediones has been developed. This new bismuth-catalyzed direct carbon-carbon bond forming reaction provides the corresponding monoalkylated dicarbonyl compounds in high yields after short reaction times using the lowest amounts of catalyst (1 mol %) and the free alcohol. In addition, a new route to substituted indenes is presented.

Regioselective allylic alkylation and etherification catalyzed by in situ generated N-heterocyclic carbene ruthenium complexes

Gürbüz, Nevin,?zdemir, Ismail,?etinkaya, Bekir,Renaud, Jean-Luc,Demerseman, Bernard,Bruneau, Christian

, p. 535 - 538 (2007/10/03)

Benzimidazolium halides are used for the first time as ligand precursors in ruthenium-catalyzed substitution of allylic carbonates and chlorides by carbon nucleophiles and phenols, respectively. After generation of diaminocarbene species upon deprotonatio

Direct carbon-carbon bond formation from alcohols and active methylenes, alkoxyketones, or indoles catalyzed by indium trichloride

Yasuda, Makoto,Somyo, Toshio,Baba, Akio

, p. 793 - 796 (2007/10/03)

(Chemical Equation Presented) The unsalted variety: The direct coupling reaction of alcohols with active methylenes, alkoxyketones, or indoles catalyzed by InCl3 proceeds without the formation of metal salts (see scheme). As H2O is the only by-product of this system, the alkylated products are easily isolated in pure form, and the reaction is suitable for large-scale synthesis.

Ruthenium-bisimine: A new catalytic precursor for regioselective allylic alkylation

Renaud, Jean-Luc,Bruneau, Christian,Demerseman, Bernard

, p. 408 - 410 (2007/10/03)

New complexes [Cp*Ru(bisimine)Cl] are active catalysts for the regioselective alkylation of allylic carbonates by soft carbonucleophiles, in favour of the branched isomers. The catalysts can be conveniently prepared in situ from [Cp*Ru(cod)Cl] and a bulky aromatic bisimine.

Copper(I) promoted C-C bond forming reactions: direct activation of allyl alcohols

Baruah, Jubaraj B.,Samuelson, Ashoka G.

, p. C57 - C60 (2007/10/02)

Allylic alcohols, acetates, carbonates and chlorides can be activated by copper(I) salts towards nucleophilic substitution by carbon nucleophiles under relatively mild conditions.

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