71504-26-2 Usage
Description
(E)-1-(trimethylsilyl)buta-1,3-diene is an organic compound that features a conjugated diene system with a trimethylsilyl group attached to the terminal carbon. This unique structure endows it with specific reactivity and stability, making it a valuable building block in organic synthesis.
Uses
Used in Organic Synthesis:
(E)-1-(trimethylsilyl)buta-1,3-diene is used as a diene in Diels-Alder reactions for the creation of allylsilanes. These allylsilanes can be further converted to a variety of functionalized cyclohexenes, which have a double bond shifted from its original position in the cyclo addition. This property makes it a versatile intermediate for the synthesis of complex organic molecules.
Used in the Synthesis of Chiral Allylboranes:
(E)-1-(trimethylsilyl)buta-1,3-diene is also used as a precursor for the synthesis of chiral allylboranes. These chiral allylboranes are important reagents in asymmetric synthesis, allowing for the selective formation of enantiomerically pure compounds, which are crucial in pharmaceutical and agrochemical industries.
Used in the Synthesis of Allylsilanes and Trienes:
Furthermore, (E)-1-(trimethylsilyl)buta-1,3-diene is utilized in the synthesis of other allylsilanes and trienes, which are valuable intermediates in the preparation of various organic compounds, including natural products, pharmaceuticals, and specialty chemicals. The presence of the trimethylsilyl group enhances the stability and reactivity of these intermediates, facilitating their use in a wide range of chemical transformations.
Preparation
(E)-1-Trimethylsilyl-1,3-butadiene is prepared geometrically pure by Wittig.
or Peterson reactions on (E)-3-trimethylsilylpropenal, by
pyrolysis of silylated 3-sulfolenes, and by coupling (E)-2-trimethylsilylvinyl bromide with lithium divinylcuprate. It
can also be prepared geometrically impure, but largely (E),
from allyltrimethylsilane by a vinylogous Ramberg–B?cklund reaction, and from 1,3-butadienyl-1-magnesium chloride and chlorotrimethylsilane.
Check Digit Verification of cas no
The CAS Registry Mumber 71504-26-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,5,0 and 4 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 71504-26:
(7*7)+(6*1)+(5*5)+(4*0)+(3*4)+(2*2)+(1*6)=102
102 % 10 = 2
So 71504-26-2 is a valid CAS Registry Number.
71504-26-2Relevant articles and documents
Une synthese hautement stereoselective de dienes conjugues (E)
Bloch, R.,Abecassis, J.,Hassan, D.
, p. 2019 - 2024 (2007/10/02)
A general method for the preparation of (E) terminal conjugated dienes was developed by the flash thermolysis of 2-substituted 2,5-dihydrothiophene-1,1-dioxides generated by a retro Diels-Alder reaction.This process allows the obtention of conjugated dienes, bearing or not a functionality (alcohols, esters), with an excellent stereoisomeric purity (in general higher than 98percent).An application to the synthesis of (E)-9,11-dodecadien-1-yl acetate, the major component of the sex pheromone of Diparopsis castanea, shows the generality and the efficacy of this method.
The Diels-Alder Route to Allylsilanes from 1-Trimethylsilylbutadienes
Carter, Martin J.,Fleming, Ian,Percival, Alan
, p. 2415 - 2434 (2007/10/02)
The synthesis and Diels-Alder reactions of 1-trimethylsilylbutadiene (3) and its 3-methyl (17), 3-trimethylsilyloxy (20), 4-methyl (4), and 4-trimethylsilyl (6) derivatives are reported.The silyl group reduces somewhat the rate of the Diels-Alder reactions, and has, if anything, a small 'ortho'-directing effect on the regioselectivity in the reactions of (3) with methyl acylate, methyl propiolate, citraconic anhydride, and 2,6-dimethylbenzoquinone.The other substituent in the dienes (17), (20), and (4) is therefore the major influence on the regioselectivity in the reactions of these dienes with methyl acrylate and methyl propiolate.The products of the Diels-Alder reactions of (3), (17), and (4) are allylsilanes, which undergo clean protodesilylation with acid, and, with the acid and ester derived from the maleic anhydride adduct of (3), undergo epoxidation and sulphenylation reactions giving an allyl alcohol (33) and an allyl sulphide (37), respectively.The adducts from (20) can be hydrolysed to β-silylketones, which can be converted into enones by bromination. 1-Pentamethyldisilylbutadiene (15) is no more reactive and no more regioselective than (3).The 'ortho'-adduct (42) from the reaction of (3) and methyl propiolate aromatises with DDQ to give methyl m-trimethylsilylbenzoate (53) in high yield, in a reaction involving rearrangement of the silyl group, even though a direct dehydrogenation is an available pathway.
