576-12-5

Basic information

• Product Name: 2-(TRIFLUOROACETYL)INDAN-1-ONE
• Synonyms: 2-(TRIFLUOROACETYL)INDAN-1-ONE;2-TRIFLUOROACETYL-1-INDANONE;2-(2,2,2-Trifluoroacetyl)-2,3-dihydro-1H-inden-1-one;2-(2,2,2-Trifluoroacetyl)indan-1-one
• CAS NO: 576-12-5
• Molecular Formula: C11H7F3O2
• Molecular Weight: 228.17
• Mol File: 576-12-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(TRIFLUOROACETYL)INDAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIFLUOROACETYL)INDAN-1-ONE(576-12-5)
• EPA Substance Registry System: 2-(TRIFLUOROACETYL)INDAN-1-ONE(576-12-5)

Safety Data

• Hazardous Substances Data: 576-12-5(Hazardous Substances Data)

Usage

General Description

2-(trifluoroacetyl)indan-1-one is a chemical compound with the molecular formula C11H7F3O. It is a yellow crystalline solid that is commonly used as a reagent in organic synthesis and pharmaceutical research. 2-(TRIFLUOROACETYL)INDAN-1-ONE is known for its strong electron-withdrawing properties due to the presence of the trifluoroacetyl group, making it a useful building block in the development of various pharmaceutical and agrochemical products. Its unique structure and properties make it a valuable tool in the field of medicinal chemistry and drug discovery.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 83-33-0 inden-1-one 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 

Relevant articles and documents

Stereoarrayed CF3-Substituted 1,3-Diols by Dynamic Kinetic Resolution: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation

CF3-substituted 1,3-diols were stereoselectively prepared in excellent enantiopurity and high yield from CF3-substituted diketones by using an ansa-ruthenium(II)-catalyzed asymmetric transfer hydrogenation in formic acid/triethylamine. The intermediate mono-reduced alcohol was also obtained in very high enantiopurity by applying milder reaction conditions. In particular, CF3C(O)-substituted benzofused cyclic ketones underwent either a single or a double dynamic kinetic resolution during their reduction. Doubling up: A double dynamic kinetic resolution is described for the ansa-ruthenium(II)-catalyzed asymmetric transfer hydrogenation of diketones in formic acid/triethylamine to yield the title compounds, displaying a stereotriad, in excellent stereopurity. The intermediate mono-reduced alcohols were isolated in very high enantiopurity by using milder reaction conditions.

Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine

An efficient method for the α-methylenation of carbonyl groups is reported, and this transformation is accomplished by a facile elimination of trifluoroacetate during the formation of the olefin. This method represents an improvement beyond existing protocol in cases of steric hindrance, and we have demonstrated the utility of the process across a series of ketones, lactams, and lactones. Additionally, we have applied this method to produce semisynthetic derivatives of the natural products (+)-sclareolide and (-)-eburnamonine, in which the carbonyl group is proximal to bulky functional groups. Mechanistic insight is also provided from a time course of 19F NMR. Biological evaluation of the natural-product-derived enones led to the identification of a derivative of (-)-eburnamonine with significant cytotoxicity (LC50 = 14.12 ?M) in drug-resistant MDA-MB-231 breast cancer cells.