3092-20-4

Basic information

• Product Name: DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE
• Synonyms: DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE;DIETHYL 2-PHENYLCYCLOPROPANE-1,1-DICARBOXYLATE
• CAS NO: 3092-20-4
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.3
• Mol File: 3092-20-4.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 324.1°C at 760 mmHg
• Flash Point: 153°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.000252mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE(3092-20-4)
• EPA Substance Registry System: DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE(3092-20-4)

Safety Data

• Hazardous Substances Data: 3092-20-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 36, p. 3517, 1980 DOI: 10.1016/0040-4020(80)88047-1

InChI:InChI=1/C15H18O4/c1-3-18-13(16)15(14(17)19-4-2)10-12(15)11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3

Upstream product

• 5292-53-5 diethyl benzalmalonate 
• 70775-39-2 dimethylsulfoxonium methylide 
• 100-42-5 styrene 
• 20165-81-5 diethyl dichloromalonate 
• 2181-42-2 trimethylsulphonium iodide 
• 15277-68-6 bis(ethoxycarbonyl)(phenyliodinio)methanide 
• 105-53-3 diethyl malonate 
• 100-52-7 benzaldehyde 
• 5256-74-6 1,3-diethyl 2-diazopropanedioate 
• 75326-15-7 (2-bromo-1-phenylethyl)dimethylsulphonium bromide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 685-87-0 Diethyl 2-bromomalonate 
• 631-22-1 diethyl dibromomalonate 
• 38066-17-0 Methyl-phenyl-sulfonium-diethoxyphosphinyl-methylid 

Downstream Products

• 3092-22-6 1-(ethoxycarbonyl)-2-phenylcyclopropanecarboxylic acid 

Relevant articles and documents

A practical and reusable catalyst for the synthesis of donor-acceptor cyclopropane

Herein, a convenient, recyclable and inexpensive Cu-based catalytic system is developed for the synthesis of donor-acceptor (D-A) cyclopropane via the cycloaddition of styrene derivatives with diethyl bromomalonate. A core-shell catalyst of Fe3

Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates

A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.