473733-73-2

Basic information

• Product Name: (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal
• Synonyms: (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal
• CAS NO: 473733-73-2
• Molecular Weight: 280.194
• Mol File: 473733-73-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal(473733-73-2)
• EPA Substance Registry System: (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal(473733-73-2)

Safety Data

• Hazardous Substances Data: 473733-73-2(Hazardous Substances Data)

Upstream product

• 62055-46-3 3-ethoxy-2-methylacrolein 
• 104371-20-2 (S)-1-(2',3',4',5',6'-perfluorophenyl)ethanol 

Downstream Products

• 358725-37-8 (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene 

Relevant articles and documents

One-pot, asymmetric and diastereoselective four-component synthesis of polyfunctional (Z)-alkenyl methyl sulfones with three stereogenic centers

The reaction of 1-(trimethylsilyloxy)cyclopentene (9) with (±)-1,3,5-triisopropyl-2-(1-(RS)-[[(1E)-2-methylpenta-1, 3-dienyl]oxy]ethyl)benzene ((±)-4a) in SO2/CH2Cl2 containing (CF3SO2)2NH, followed by treatment with Bu4NF and MeI gave a 3.0:1 mixture of (±)-(2RS)-2{(1RS,2Z,4SR)-2-methyl-4-(methylsulfonyl)-1-[(RS) -1-(2,4,6-triisopropylphenyl)ethoxy]pent-2-en-1-yl}cyclopentanone ((±)-10) and (±)-(2RS)-2{(1RS,2Z)-2-methyl-4-[(SR)-methylsulfonyl]-1-[(SR)-1 -(2,4,6-triisopropylphenyl)ethoxy]pent-2-en-1-yl}cyclopentanone ((±)-11). Similarly, enantiomerically pure dienyl ether (-)-(1S)-4a reacted with 1-(trimethylsilyloxy)cyclohexene (12) to give a 14.1:1 mixture of (-)-(2S)-2-{(1S,2Z,4R)-2-methyl-4-(methylsulfonyl)-1-[(S)-1-(2,4, 6-triisopropylphenyl)ethoxy]pent-2-enyl}cyclohexanone ((-)-13a) and its diastereoisomer 14a with (1S,2R,4R) or (1R,2S,4S) configuration. Structures of (±)-10, (±)-11, and (-)-13a were established by single-crystal X-ray crystallography. Poor diastereoselectivities were observed with the (E,E)-2-methylpenta-1,3-diene-1-ylethers (+)-4b and (-)-4c bearing (1S)-1-phenylethyl and (1S)-1-(pentafluorophenyl)ethyl groups instead of the Greene's auxiliary ((1S)-(2,4,6-triisopropylphenyl)ethyl group). The results demonstrate that high α/β-syn and asymmetric induction (due to the chiral auxiliary) can be obtained in the four-component syntheses of the β-alkoxy ketones. The method generates enantiomerically pure polyfunctional methyl sulfones bearing three chiral centers on C-atoms and one (Z)-alkene moiety.