80352-59-6

Basic information

• Product Name: 1-(trimethylsilyl)hex-1-yn-3-one
• CAS NO: 80352-59-6
• Molecular Formula: C₉H₁₆OSi
• Molecular Weight: 168.3082
• Mol File: 80352-59-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 190.3°C at 760 mmHg
• Flash Point: 68.9°C
• Density: 0.87g/cm³
• Vapor Pressure: 0.545mmHg at 25°C
• Refractive Index: 1.435
• CAS DataBase Reference: 1-(trimethylsilyl)hex-1-yn-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(trimethylsilyl)hex-1-yn-3-one(80352-59-6)
• EPA Substance Registry System: 1-(trimethylsilyl)hex-1-yn-3-one(80352-59-6)

Safety Data

• Hazardous Substances Data: 80352-59-6(Hazardous Substances Data)

Usage

Type of compound

Silyl enol ether

Structure

Contains a silicon atom attached to an oxygen atom, which is doubly bonded to a carbon atom

Functional groups

a. Carbon-carbon triple bond
b. Trimethylsilyl group

Common use

Reagent in organic synthesis

Applications

a. Formation of carbon-carbon bonds
b. Preparation of various organic compounds
c. Studies on natural product synthesis
d. Medicinal chemistry

Role of trimethylsilyl group

Enhances stability and reactivity of the attached carbon-carbon triple bond

Importance

Valuable tool in the field of organic chemistry

Upstream product

• 17874-23-6 1,2-Hexadienyltrimethylsilan 
• 141-75-3 butyryl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 1066-54-2 trimethylsilylacetylene 
• 106-31-0 butanoic acid anhydride 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 

Downstream Products

• 689-00-9 hex-1-yn-3-one 
• 1356145-61-3 N'-(1-(5-cyanopyrazolo[1,5-a]pyridin-3-yl)butylidene)-2-methyl-5-nitrobenzenesulfonohydrazide 
• 1356145-69-1 N'-(1-(5-cyanopyrazolo[1,5-a]pyridin-3-yl)butylidene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide 

Relevant articles and documents

Propargylic C[sbnd]H activation using a Cu(II) 2-quinoxalinol salen catalyst and tert-butyl hydroperoxide

The oxidation of alkynes to α,β-acetylenic carbonyls was achieved using only 1 mol% of a Cu(II) 2-quinoxalinol salen catalyst with tert-butyl hydroperoxide. These reactions proceed under mild conditions (70 °C) with excellent selectivity, producing yields up to 78%, and were used on a variety of alkyne substrates to produce the desired corresponding α,β-acetylenic ketones. In addition, these reactions can be run under aqueous conditions using a sulfonated version of the 2-quinoxalinol salen with good yields, reducing the need for volatile organic solvents.

Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors

We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110α isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a]pyridine ring system, and found compound 5x to be a particularly potent example (p110α IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model.

PYRAZOLO[1,5-A]PYRIDINE AND IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AND THEIR USE IN CANCER THERAPY

The invention relates to pyrazolo[1,5-a]pyridine and/or -imidazo[1,2-a]pyridine derivatives, to their preparation, to their use as agents or drugs for cancer prevention or therapy for treating cancer, either alone or in combination with radiation and/or anticancer drugs.