7382-06-1

Basic information

• Product Name: ethyl 2,3-diphenylcycloprop-2-ene-1-carboxylate
• CAS NO: 7382-06-1
• Molecular Formula: C₁₈H₁₆O₂
• Molecular Weight: 264.3184
• Mol File: 7382-06-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 357.5°C at 760 mmHg
• Flash Point: 163.8°C
• Density: 1.174g/cm³
• Vapor Pressure: 2.71E-05mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: ethyl 2,3-diphenylcycloprop-2-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3-diphenylcycloprop-2-ene-1-carboxylate(7382-06-1)
• EPA Substance Registry System: ethyl 2,3-diphenylcycloprop-2-ene-1-carboxylate(7382-06-1)

Safety Data

• Hazardous Substances Data: 7382-06-1(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 501-65-5 diphenyl acetylene 

Relevant articles and documents

Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes

A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.

Cu(I)-Catalyzed Intramolecular Tandem Cyclization of N-Indole-Tethered Cyclopropenes: Synthesis of Functionalized Hydrogenated Diazabenzo[ a]cyclopenta[ cd]azulene Derivatives

A Cu(I)-catalyzed [3 + 2] intramolecular cycloaddition reaction of N-indole-tethered cyclopropenes is presented in this paper. This reaction starts from the formation of ?-allyl cationic intermediate or its resonance-stabilized metal carbenoid intermediate upon activation of cyclopropene with Cu(I) catalyst and a Friedel-Crafts-type cyclization to give functionalized hydrogenated diazabenzo[a]cyclopenta[cd]azulenes in good to excellent yields along with moderate to good dr values. The asymmetric variant of this cycloaddition reaction can be realized, giving the desired products with moderate ee values.

RhI-Catalyzed Carbonylative [3+1] Construction of Cyclobutenones via C?C σ-Bond Activation of Cyclopropenes

With a catalytic amount of Rh(cod)2BF4 and dppm, cyclopropenes undergo a direct carbonylative [3+1] cycloaddition reaction under an atmosphere of CO to produce the cyclobutenones in excellent yields, in which the regio- and diastereoselectivities can be controlled in certain cases with the help of chelating groups. Cyclobutenone with a chiral 4-position was prepared by diastereoselective induction. Rhodacyclopentenone has been determined as the key intermediate, as it was synthesized and applied to the reductive elimination step.