51425-55-9

Basic information

• Product Name: (E)-dihydrocinnamaldehyde trimethyl silyl enol ether
• Synonyms: (E)-dihydrocinnamaldehyde trimethyl silyl enol ether
• CAS NO: 51425-55-9
• Molecular Weight: 206.36
• Mol File: 51425-55-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (E)-dihydrocinnamaldehyde trimethyl silyl enol ether(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-dihydrocinnamaldehyde trimethyl silyl enol ether(51425-55-9)
• EPA Substance Registry System: (E)-dihydrocinnamaldehyde trimethyl silyl enol ether(51425-55-9)

Safety Data

• Hazardous Substances Data: 51425-55-9(Hazardous Substances Data)

Upstream product

• 109283-53-6 (E)-cinnamyloxytrimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 107-02-8 acrolein 
• 104-53-0 3-phenyl-propionaldehyde 
• 108-86-1 bromobenzene 
• 105762-68-3 3-Phenyl-2-phenylsulfanyl-1-trimethylsilanyl-propan-1-ol 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 122-78-1 phenylacetaldehyde 
• 4432-63-7 2-phenylacrolein 
• 14371-10-9 (E)-3-phenylpropenal 
• 128586-68-5 2-allyl-3-phenylpropionaldehyde 

Relevant articles and documents

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates

An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.

Mechanistic analysis of the photocycloaddition of silyl-tethered alkenes

(Chemical Equation Presented) The photochemistry of substituted cinnamyloxy silanes has been examined in both cyclohexane and acetonitrile solvents. Alkene isomerization occurs in addition to cycloaddition. Fluorescence quantum yields and excited singlet state lifetimes have been determined for each compound. We have used the information in order to better understand the regio- and stereoselectivity of photocycloaddition between silyl-tethered cinnamyl groups. This study allows us to conclude that the 2 + 2 photocycloaddition between alkenes is not a Woodward-Hoffmann orbital symmetry controlled event. The most consistent explanation for the excellent regio- and stereoselectivity is that the photocycloaddition is conformationally controlled.

Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride

Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N- dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.