699005-11-3

Basic information

• Product Name: 2-Cyclopropene-1-carboxylic acid, 1-phenyl-2-(trimethylsilyl)-, methyl ester
• CAS NO: 699005-11-3
• Molecular Formula: C14H18O2Si
• Molecular Weight: 246.381
• Mol File: 699005-11-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Cyclopropene-1-carboxylic acid, 1-phenyl-2-(trimethylsilyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopropene-1-carboxylic acid, 1-phenyl-2-(trimethylsilyl)-, methyl ester(699005-11-3)
• EPA Substance Registry System: 2-Cyclopropene-1-carboxylic acid, 1-phenyl-2-(trimethylsilyl)-, methyl ester(699005-11-3)

Safety Data

• Hazardous Substances Data: 699005-11-3(Hazardous Substances Data)

Upstream product

• 101-41-7 benzeneacetic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 21233-61-4 quinoline-4-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Diastereoselective Trapping of Transient Carboxylic Oxonium Ylides with α,β-Unsaturated 2-Acyl Imidazoles

By developing a diastereoselective reaction of cyclopropene carboxylic acids with α,β-unsaturated 2-acyl imidazoles, we reported here a Michael-type trapping of transient carboxylic oxonium ylides. This transformation provides a direct approach for the construction of valuable γ-butenolide derivatives in good yields (60–99%) with high diastereoselectivities (up to >95:5 dr) under mild reaction conditions. (Figure presented.).

Enantioselective, facially selective carbomagnesation of cyclopropenes

Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step. Copyright