54125-02-9 Usage
Description
1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE, also known as Danishefsky's diene, is a functionalized Diels-Alder diene with significant synthetic utility in organic chemistry. It is characterized by its methoxy and trimethylsiloxy groups, which contribute to its reactivity and versatility in various chemical reactions.
Uses
Used in Pharmaceutical Synthesis:
1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE is used as a reagent in the Mannich-Michael reaction for the synthesis of piperidinones and enaminones. These compounds are important building blocks in the development of various pharmaceuticals, particularly those targeting the central nervous system and other therapeutic applications.
Used in Organic Synthesis:
As a Diels-Alder diene, 1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE is employed in the synthesis of various heterocyclic compounds, such as pyridones, pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins), 4H-1-aminopyrroles, and 4,5H-pyrazoles. These compounds have diverse applications in the fields of pharmaceuticals, agrochemicals, and materials science.
Used in Asymmetric Hetero-Diels-Alder Cyclization:
1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE is used in asymmetric hetero-Diels-Alder cyclization reactions, where it reacts with benzaldehyde in the presence of mesoporous inorganic/metalorganic hybrid materials as catalysts. This process allows for the selective formation of complex heterocyclic structures with potential applications in the development of novel pharmaceuticals and other specialty chemicals.
Used in Mukaiyama-Michael-type Addition/Heterocyclization:
1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE is also utilized in Mukaiyama-Michael-type addition/heterocyclization reactions with 1,2-diaza-1,3-butadiene. This reaction provides access to a range of nitrogen-containing heterocycles, which are valuable intermediates in the synthesis of biologically active compounds and advanced materials.
Purification Methods
It may contain up to 1% of the precursor 4-methoxybut-4-ene-2-one. It is easily purified by distilling through a Vigreux column (p 11) in a vacuum and taking the middle fraction. [Danishefsky & Kitihara J Am Chem Soc 96 7807 1974, Danishefsky Acc Chem Res 14 400 1981.]
Check Digit Verification of cas no
The CAS Registry Mumber 54125-02-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,1,2 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 54125-02:
(7*5)+(6*4)+(5*1)+(4*2)+(3*5)+(2*0)+(1*2)=89
89 % 10 = 9
So 54125-02-9 is a valid CAS Registry Number.
54125-02-9Relevant articles and documents
Unexpected regioselectivity in the synthesis of pyranonaphthoquinone via the diels-alder reaction
Cui, Yi,Jiang, Hao,Li, Zhengtao,Wu, Na,Yang, Zhen,Quan, Junmin
, p. 4628 - 4631 (2009)
The unusual regioselectivity In the Diels-Alder reactions of pyranoquinone 1 with (4,4-dlmethoxybuta-1,3-dlen-2-yloxy)trimethylsilane 2 are explored by both computations and experiments. The regioselectivity Is controlled by the electrostatic interaction of the lactone ring-oxygen and the vicinal quinone oxygen on the transition structure, which can be tuned by the terminal methyl group of the butadienes.
Enantioselective Formal [4+1] Cycloaddition of Diazoarylacetates and the Danishefsky's Diene: Stereoselective Synthesis of (-)-1,13-Herbertenediol
Hu, Fang,Zhou, Qing,Cao, Fei,Chu, Wen-Dao,He, Long,Liu, Quan-Zhong
, p. 12806 - 12814 (2018)
Rodium chiral diene complex-catalyzed enantioselective cycloaddition of aryl α-diazoarylacetates and electron-enriched Danishefsky-type dienes afforded highly functionalized and optically enriched cyclopentenones in excellent yields (up to 97% yield) and
Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides
Gueret, Stephanie M.,Furkert, Daniel P.,Brimble, Margaret A.
supporting information; experimental part, p. 5226 - 5229 (2011/02/23)
The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.
