21175-42-8

Usage

Type

Synthetic organic chemical

Use

Fragrance creation

Applications

Perfumes, cosmetics, food items, pharmaceuticals

Odor

Sweet, caramel-like

Natural sources

Cocoa, coffee

Potential properties

Anticancer, antimicrobial

Upstream product

• 3183-15-1 4-oxo-5-phenylvaleric acid 
• 300-57-2 allylbenzene 
• 174720-07-1 5-phenyl-γ-hydroxyvaleric acid 
• 591-80-0 pent-4-enoic acid 
• 98-80-6 phenylboronic acid 
• 64-19-7 acetic acid 
• 140-29-4 phenylacetonitrile 
• 19881-97-1 3-phenylpropane-1,2-diol 
• 105-53-3 diethyl malonate 
• 108-24-7 acetic anhydride 
• 1729-32-4 5-iodomethyl-dihydro-furan-2-one 
• 591-50-4 iodobenzene 
• 108-95-2 phenol 
• 1269657-62-6 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate 

Downstream Products

• 91025-54-6 N-(3,4,5-trimethoxyphenethyl)-5-phenyl-4-hydroxypentanamide 
• 924893-87-8 4-hydroxy-N,N-dimethyl-5-phenylpentanamide 
• 924893-94-7 (S)-4-hydroxy-N,N-dimethyl-5-phenylpentanamide 
• 1380503-45-6 (S)-4-(dimethylcarbamoyl)-1-phenyl-2-butyl acetate 
• 415902-37-3 (S)-5-benzyl-dihydrofuran-2(3H)-one 
• 437606-63-8 (R)-5-phenyl-γ-valerolactone 
• 1380503-44-5 4-(dimethylcarbamoyl)-1-phenyl-2-butyl acetate 
• 1380503-46-7 (R)-4-hydroxy-N,N-dimethyl-5-phenylpentanamide 
• 122715-97-3 N,N-dimethyl-4-oxo-5-phenylpentaneamide 
• 1248025-66-2 ethyl 4-hydroxy-5-phenylpentanoate 
• 1389318-72-2 C₁₉H₂₃NO₃ 
• 1389318-71-1 C₂₄H₃₁NO₅ 
• 14293-09-5 5-Phenyl-4-hydrovaleramid 
• 20371-41-9 5-phenylvaleric acid chloride 

Relevant academic research and scientific papers

Cascade Synthesis of Five-Membered Lactones using Biomass-Derived Sugars as Carbon Nucleophiles

We report the cascade synthesis of five-membered lactones from a biomass-derived triose sugar, 1,3-dihydroxyacetone, and various aldehydes. This achievement provides a new synthetic strategy to generate a wide range of valuable compounds from a single bio

Aerobic Catalytic Features in Photoredox- and Copper-Catalyzed Iodolactonization Reactions

Mechanistic evaluations and comparison of two important aerobic catalytic oxidation processes, aerobic copper catalysis and photoredox catalysis, are performed. Interesting and distinct catalytic behaviors were observed for a common reaction of iodolacton

MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones

An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

Mn(OAc)3-mediated arylation-lactonization of alkenoic acids: Synthesis of γ,γ-disubstituted butyrolactones

A general method for the oxidative cyclization of 4-alkenoic acids with arylboronic acids has been developed. The reactions described provide a novel access to γ,γ-disubstituted butyrolactones in moderate yields, and allow the direct formation of a C-C bo

Ruthenium pincer-catalyzed synthesis of substituted γ-butyrolactones using hydrogen autotransfer methodology

The ruthenium pincer-catalyzed synthesis of γ-butyrolactones from 1,2-diols and malonates using borrowing-hydrogen methodology is reported. This regioselective domino-process takes place through catalytic C-C bond formation, followed by intramolecular transesterification. Herein, we show the Ru-MACHO-BH complex as a valuable catalyst in hydrogen autotransfer reactions.

Aryl imidazylates and aryl sulfates as electrophiles in metal-free ArSN1 reactions

Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.

Chemo-, regio- and stereoselective heck arylation of allylated malonates: Mechanistic insights by ESI-MS and synthetic application toward 5-arylmethyl-γ-lactones

We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species through the catalytic cycle. Additionally, some Heck adducts were successfully used in the total synthesis of pharmacologically active γ-lactones.

Lipase-catalyzed kinetic resolution of 2-phenylethanol derivatives and chiral oxa-Pictet-Spengler reaction as the key steps in the synthesis of enantiomerically pure tricyclic amines

A series of 5,6,7,8,9,10-hexahydro-5,9-epoxybenzocycloocten-6-amines have been synthesized and pharmacologically evaluated in receptor binding studies (σ1, σ2, NMDA, κ, and μ receptors). The first key step of the synthesis was a chir

A novel convergent method for the synthesis of α-acyl-γ- hydroxylactams and its application in the total synthesis of PI-090 and 091

A novel convergent method for the synthesis of α-acyl-γ- hydroxylactams utilizing the aldol reaction of N-Boc-protected γ-methoxylactams was developed. As the first application of this method for the synthesis of biologically active natural products, the total synthesis of platelet aggregation inhibitors PI-090 and PI-091 were also investigated and successfully achieved.

Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation

A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.