20279-47-4

Basic information

• Product Name: phenethyl pyruvate
• Synonyms: phenethyl pyruvate;2-Oxopropanoic acid 2-phenylethyl ester;2-Oxopropanoic acid phenethyl ester;Einecs 243-674-3
• CAS NO: 20279-47-4
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21118
• EINECS: 243-674-3
• Mol File: 20279-47-4.mol

Chemical Properties

• Boiling Point: 303.7°Cat760mmHg
• Flash Point: 136.2°C
• Appearance: /
• Density: 1.115g/cm³
• Vapor Pressure: 0.000916mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: phenethyl pyruvate(CAS DataBase Reference)
• NIST Chemistry Reference: phenethyl pyruvate(20279-47-4)
• EPA Substance Registry System: phenethyl pyruvate(20279-47-4)

Safety Data

• Hazardous Substances Data: 20279-47-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12O3/c1-9(12)11(13)14-8-7-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

Upstream product

• 60-12-8 2-phenylethanol 
• 5704-66-5 pyruvoyl chloride 

Relevant articles and documents

Selective Carbonyl?C(sp3) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis

Carbon–carbon bond cleavage/functionalization is synthetically valuable, and selective carbonyl?C(sp3) bond cleavage/alkynylation presents a new perspective in constructing ynamides, ynoates, and ynones. Reported here is the first alkoxyl-radical-enabled carbonyl?C(sp3) bond cleavage/alkynylation reaction by photoredox catalysis. The use of novel cyclic iodine(III) reagents are essential for β-carbonyl alkoxyl radical generation from β-carbonyl alcohols, including alcohols with high redox potential (EoxP>2.2 V vs. SCE in MeCN). β-Amide, β-ester, and β-ketone alcohols yield ynamides, ynoates, and ynones, respectively, for the first time, with excellent regio- and chemoselectivity under mild reaction conditions.

Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ

We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp3 hydrocarbon tether and a sp2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.