97699-36-0

Basic information

• Product Name: Oxirane, 2-ethenyl-2-phenyl-
• Synonyms: Oxirane,2-ethenyl-2-phenyl;2-phenyl-2-vinyloxirane
• CAS NO: 97699-36-0
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Mol File: 97699-36-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Oxirane, 2-ethenyl-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, 2-ethenyl-2-phenyl-(97699-36-0)
• EPA Substance Registry System: Oxirane, 2-ethenyl-2-phenyl-(97699-36-0)

Safety Data

• Hazardous Substances Data: 97699-36-0(Hazardous Substances Data)

Upstream product

• 532-27-4 1-chloroacetophenone 
• 120609-13-4 1-Bromo-2-phenyl-3-buten-2-ol 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 
• 768-03-6 Phenyl vinyl ketone 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 1610376-74-3 (Z)-S-(4-hydroxy-3-phenylbut-2-en-1-yl) O,O-diethyl phosphorodithioate 
• 1610376-81-2 (E)-S-(4-hydroxy-3-phenylbut-2-en-1-yl) O,O-diethyl phosphorodithioate 
• 4411-89-6 (E/Z)-2-phenylcrotonaldehyde 

Relevant articles and documents

Rhodium-Catalyzed Regioselective Formal Hydroacylation of Vinyl Epoxides toward Esters Involving β-Carbon Cleavage

Herein we disclose the first example of the formal hydroacylation reactions of vinyl epoxides with chelating aldehydes enabled by rhodium catalysis for the efficient construction of functionalized esters. Detailed investigations of the mechanistic pathway reveal that the presence of a 2-vinyl group is essential in contributing to the success of this regioselective reaction, which might proceed through β-carbon cleavage as the key procedure.

Synthetic Strategy for Tetraphenyl-Substituted All-E-Carotenoids with Improved Molecular Properties

The synthetic method of tetraphenyl-substituted all-E-carotenes 1 with improved properties of antioxidant and molecular electronic conductance was developed through the formation of tetraphenyl-substituted all-E-apocarotenedial 4. The synthesis highlighted the preparation of novel subunits containing phenyl substituent(s) with E-configuration starting from the key (E)-4-chloro-2-phenylbut-2-enal (10), utilizing conjugation effect with formyl group or easy recrystallization of sulfone compounds. Sulfone-mediated coupling methods of Julia and modified Julia–Kocienski olefinations utilizing the subunits were demonstrated to produce tetraphenyl-substituted apocarotenedials 4. The major all-E-forms (73–85 % selectivity) were easily purified by SiO2 chromatography and trituration with Et2O due to the presence of the polar formyl groups. The olefination of all-E-apocarotenedials 4 and Wittig salt 5 provided all-E-9,9',13,13'-tetraphenylcarotenes 1.

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.