43209-86-5 Usage
Description
3-Trimethylsilyl-3-buten-2-one is a methyl vinyl ketone homolog characterized by its unique chemical structure and versatile reactivity. It is known for its ability to participate in various organic reactions, making it a valuable compound in the field of organic chemistry.
Uses
Used in Organic Chemistry:
3-Trimethylsilyl-3-buten-2-one is used as a Michael acceptor for annulation reactions, which are important in the synthesis of complex organic molecules and the formation of cyclic structures. Its reactivity allows for the creation of γ,δ-unsaturated ketones, which are key intermediates in the synthesis of various organic compounds.
Used in Synthesis of Dienes:
3-Trimethylsilyl-3-buten-2-one is also utilized as a precursor to a stabilized Diels-Alder diene, which is crucial in the Diels-Alder reaction, a fundamental [4+2] cycloaddition process in organic chemistry. This reaction is widely used to form six-membered rings in organic molecules, contributing to the synthesis of a wide range of natural products and pharmaceuticals.
Used in the Formation of Diene Adducts:
3-Trimethylsilyl-3-buten-2-one is employed in the formation of diene adducts, which are essential in the development of complex organic structures and have applications in various chemical industries.
Physical properties:
3-Trimethylsilyl-3-buten-2-one has a boiling point of 72 °C at a pressure of 50 mmHg, which is an important consideration when handling and utilizing this compound in various chemical processes.
Preparation
3-Trimethylsilyl-3-buten-2-one is prepared by the reaction of (1-bromovinyl)
trimethylsilane with acetaldehyde. An alternative
synthesis from acrolein has been published.
Check Digit Verification of cas no
The CAS Registry Mumber 43209-86-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,3,2,0 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 43209-86:
(7*4)+(6*3)+(5*2)+(4*0)+(3*9)+(2*8)+(1*6)=105
105 % 10 = 5
So 43209-86-5 is a valid CAS Registry Number.
43209-86-5Relevant articles and documents
Epoxidation versus Allylic Oxidation (CH Insertion) in the Oxyfunctionalization of Vinylsilanes and β-Hydroxy Derivatives by Dimethyldioxirane
Adam, Waldemar,Prechtl, Frank,Richter, Markus J.,Smerz, Alexander K.
, p. 4991 - 4994 (2007/10/02)
Epoxidation of acyclic vinylsilanes by dimethyldioxirane affords α,β-epoxysilanes in high yields, whereas for cyclic vinylsilanes appreciable amounts of allylic oxidation is observed.These competitive pathways become more pronounced, when the reactivity of the double bond is decreased by electronic and/or steric factors.
One-pot synthesis of α-trimethylsilyl enones from vinylsilanes
Adam,Richter
, p. 176 - 180 (2007/10/02)
Photooxygenation of vinylsilanes in the presence of acetic anhydride and pyridine afforded α-trimethylsilyl enones 1 in moderate to good yields. Since the required starting materials are readily available, the present approach constitutes a useful alterna
UNSYMMETRICAL MONOPROTECTED α-DIKETONES VIA THE PALLADIUM-CATALYZED VINYLATION OF ACID CHLORIDES WITH ORGANOTIN COMPOUNDS
Soderquist, John A.,Leong, William Wei-Hwa
, p. 2361 - 2362 (2007/10/02)
Under benzyl(chloro)bis triphenylphosphinepalladium(II) catalysis, α-oxygenated vinyltin compounds undergo clean cross coupling with acid chlorides to give α-oxygenated enones which are converted to unsymmetrical α-diketones, butadienyl ethers or substituted methyl vinyl ketones.
