1833-53-0 Usage
Description
ISOPROPENYLOXYTRIMETHYLSILANE, also known as (Isopropenyloxy)trimethylsilane, is an enol silyl ether with a clear colorless liquid appearance. It is known for its participation as a nucleophile in Lewis acid-promoted C3-nucleophile substitution of tetracyclic bromide and has been reported to be involved in the total synthesis of (±)-powelline. Additionally, it takes part in dityltin bis(triflate) catalyzed Michael addition reactions of enol silyl ethers.
Uses
Used in Chemical Synthesis:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a nucleophile for [Lewis acid-promoted C3-nucleophile substitution of tetracyclic bromide] because of its ability to participate in such reactions, making it a valuable component in chemical synthesis processes.
Used in Total Synthesis:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a key component in the total synthesis of [±)-powelline] due to its involvement in the synthesis process, contributing to the creation of this compound.
Used in Michael Addition Reactions:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a reactant in dityltin bis(triflate) catalyzed Michael addition reactions of enol silyl ethers for [enhancing the reaction efficiency and selectivity] as it plays a crucial role in these specific types of reactions.
Used in Pharmaceutical Industry:
ISOPROPENYLOXYTRIMETHYLSILANE is used as an intermediate or reagent in the [pharmaceutical industry] for [the synthesis of various drugs and drug candidates], given its involvement in chemical reactions that can lead to the development of new pharmaceutical compounds.
Used in Research and Development:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a research compound in [academic and industrial research] for [exploring new reaction pathways and understanding the reactivity of enol silyl ethers], as it provides valuable insights into the behavior of such compounds in various chemical reactions.
Purification Methods
Purify it by fractional distillation using a very efficient column at atmospheric pressure. It usually contains 5% of hexamethyldisiloxalane which boils at 99-101o, but is generally non-reactive and need not be removed. [Hauser & Hance J Am Chem Soc 71 5091 1952.] It has been distilled under N2 through a 15cm column packed with glass helices. Fraction b 99-104o is further purified by gas chromatography through a Carbowax column (Autoprep A 700) at a column temperature of 87o, and has a retention time of 9.5minutes. [Krüger & Rochow J Organomet Chem 1 476 1963-4.]
Check Digit Verification of cas no
The CAS Registry Mumber 1833-53-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,3 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1833-53:
(6*1)+(5*8)+(4*3)+(3*3)+(2*5)+(1*3)=80
80 % 10 = 0
So 1833-53-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H14OSi/c1-6(2)7-8(3,4)5/h1H2,2-5H3
1833-53-0Relevant articles and documents
Gusel'nikov et al.
, p. 18,22 (1975)
Tandem 1,4-addition reactions with benzene and alkylated benzenes promoted by pentaammineosmium(II)
Ding, Fei,Kopach, Michael E.,Sabat, Michal,Harman, W. Dean
, p. 13080 - 13087 (2002)
Electrophiles such as dimethoxymethane and 3-penten-2-one react with the complex [Os(NH3)5-(η2-benzene)]2+ in the presence of triflic acid to form metastable benzenium intermediates. These benzenium intermediates further react with carbon nucleophiles including silyl ketene acetals, (silyloxy)alkenes, and phenyllithium in an overall tandem 1,4-addition sequence. The metal fragment controls the relative stereo- and regiochemistry for both electrophilic and nucleophilic addition steps. Upon oxidative demetalation with silver triflate, cis-1,4 cyclohexadienes are formed in yields ranging from 16 to 82%. This methodology can also be used to dearomatize toluene and ortho- and meta-xylene with unexpectedly high regio- and stereocontrol.
Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis
Fujimoto, Hayato,Kusano, Momoka,Kodama, Takuya,Tobisu, Mamoru
supporting information, p. 18394 - 18399 (2021/11/22)
We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.
Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes
Zhang, Changhe,Lupton, David W.
supporting information, p. 4456 - 4459 (2017/09/11)
An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.