5-phenylpenta-2,4-dienal

CAS

13466-40-5

Catalog Number

ACM13466405

Category

Main Products

Molecular Weight

158.19

Molecular Formula

C11H10O

MSDS COA Spec Sheet

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Specification

Synonyms

5-Phenyl-2,4-pentadienal

Appearance

Yellow liquid

Study on the Selectivity of the Addition Reaction of 5-Phenyl-2,4-Pentadienal to α,β-γ,δ-Diunsaturated Aldehydes

Hayashi, Yujiro, et al. ChemCatChem, 2012, 4(7), 959-962.

In order to study the 1,4- and 1,6-selectivity in the conjugate addition of α,β-γ,δ diunsaturated aldehydes, the reaction of 5-phenyl-2,4-pentadienal with nitromethane was used as a model and the reaction conditions were studied. The results show that the 1,4-addition reaction is the main reaction mode of the Michael addition reaction of α,β-γ,δ-diunsaturated aldehydes.
Addition reaction of 5-Phenyl-2,4-pentadienal
· The diphenylprolinol silyl ether serves as a highly efficient catalyst for the Michael reaction involving α,β-unsaturated aldehydes and nitromethane, specifically using diphenylprolinol trimethylsilyl ether 1. When 5-phenyl-2,4-pentadienal is reacted with nitromethane in the presence of catalyst 1 and benzoic acid in methanol, the process smoothly generates a 1,4-addition product with a yield of 70% and 85% ee. Importantly, no formation of a 1,6-addition product was observed.
· To enhance the enantioselectivity, a further examination of the reaction conditions was conducted. It was determined that catalysts with bulkier substituents on the silicon atom yielded improved enantioselectivity. The diphenylmethylsilyl ether of diphenylprolinol (3) demonstrated remarkable enantioselectivity, achieving 94% ee.
· Furthermore, not only does nitromethane react with 5-phenyl-2,4-pentadienal, but cyclopentadiene and nitroethanol also participate, resulting in the formation of the 1,4-addition product with good yields and enantioselectivities ranging from high to excellent. Again, no 1,6-addition products were detected in these cases.

Cascade Catalytic Reaction of 5-Phenyl-2,4-Pentadienal and Cinnamaldehyde

Shi, Yuanyuan, et al. Nanoscale Advances, 2019, 1(9), 3654-3659.

In the presence of O2, K2CO3 and ethanol, cinnamaldehyde can be converted into oxygenated compounds and C11 and C13 hydrocarbons through a primary cascade reaction of oxidative esterification, aldol condensation and Michael addition over Au/NiO catalyst. Among them, esters (ethyl cinnamate (EC) and ethylcinnamylideneacetate (ECDA)) and furan derivatives (benzylfuran (BF) and cinnamylfuran (CF)) can be obtained through oxidative esterification, aldol condensation and Michael addition of cinnamaldehyde and 5-phenyl-2,4-pentadienal, respectively.
aldol condensation
Single-pot cascade experimental procedures
· The Au/oxide catalysts, which include oxides such as NiO, SiO2, TiO2, or CeO2, are easily synthesized through a wet-chemical method utilizing polyvinyl alcohol-stabilized Au colloids along with oxide powders.
· The one-pot cascade reactions were conducted at a temperature of 130 °C and a pressure of 1 MPa of air in a 10 mL reactor over a duration of 4 hours. Initially, the reactor was filled with 3 mL of ethanol, 40 mg of cinnamaldehyde, and 10 mg of the catalyst. During the hydrodeoxygenation process, the reactor's atmosphere was switched to 1 MPa of H2 gas. The resulting supernatant was analyzed using gas chromatography-mass spectrometry (GC-MS) equipped with an MS-5977 and an HP-5MS capillary column, which enabled the assessment of conversion rates and product selectivity.

What is the molecular formula of 5-phenylpenta-2,4-dienal?

The molecular formula of 5-phenylpenta-2,4-dienal is C11H10O.

What is the molecular weight of 5-phenylpenta-2,4-dienal?

The molecular weight of 5-phenylpenta-2,4-dienal is 158.20 g/mol.

When was 5-phenylpenta-2,4-dienal created?

5-phenylpenta-2,4-dienal was created on April 28, 2006.

What is the InChI of 5-phenylpenta-2,4-dienal?

The InChI of 5-phenylpenta-2,4-dienal is "InChI=1S/C11H10O/c12-10-6-2-5-9-11-7-3-1-4-8-11/h1-10H/b6-2+,9-5+".

What is the InChIKey of 5-phenylpenta-2,4-dienal?

The InChIKey of 5-phenylpenta-2,4-dienal is "UWTZBVTWSKWXMN-VDESZNBCSA-N".

What is the canonical SMILES of 5-phenylpenta-2,4-dienal?

The canonical SMILES of 5-phenylpenta-2,4-dienal is "C1=CC=C(C=C1)C=CC=CC=O".