31469-26-8

Basic information

• Product Name: 3,5-Dioxa-2,6-disilaheptane, 2,2,6,6-tetramethyl-4-(1-phenylethylidene)-
• CAS NO: 31469-26-8
• Molecular Formula: C15H26O2Si2
• Molecular Weight: 294.541
• Mol File: 31469-26-8.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Dioxa-2,6-disilaheptane, 2,2,6,6-tetramethyl-4-(1-phenylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dioxa-2,6-disilaheptane, 2,2,6,6-tetramethyl-4-(1-phenylethylidene)-(31469-26-8)
• EPA Substance Registry System: 3,5-Dioxa-2,6-disilaheptane, 2,2,6,6-tetramethyl-4-(1-phenylethylidene)-(31469-26-8)

Safety Data

• Hazardous Substances Data: 31469-26-8(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 492-37-5 hydratropic acid 

Downstream Products

• 492-37-5 hydratropic acid 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 1071459-99-8 6-(ethanoyloxy)-2-methyl-2-phenylhex-4-enoic acid 
• 28645-07-0 (S)-methyl 2-phenylpropanoate 
• 7782-26-5 (R)-2-Phenylpropionic acid 
• 40348-57-0 Trimethylsilyl-α-phenylpropionat 

Relevant articles and documents

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Enantioselective protonation is a potent and efficient way to construct chiral carbons. Here we report details of the reaction using Lewis acid-assisted chiral Bronsted acids (chiral LBAs). The 1:1 coordinate complex of tin tetrachloride and optically active binaphthol ((R)- or (S)-BINOL) can directly protonate various silyl enol ethers and ketene disilyl acetals to give the corresponding α-aryl ketones and α-arylcarboxylic acids, respectively, with high enantiomeric excesses (up to 98% ee). A catalytic version of enantioselective protonation has also been achieved using stoichiometric amounts of 2,6-dimethylphenol and catalytic amounts of monomethyl ether of optically active BINOL in the presence of tin tetrachloride. This protonation is also effective for producing α-halocarbonyl compounds (up to 91% ee). DFT calculations on the B3LYP/LANL2DZ level show that the conformational structure of the chiral LBA and the orientation of activated proton on (R)-BINOLs are important for understanding the absolute stereochemistry of the products.