212830
trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene
95%
Synonym(s):
Danishefsky’s diene
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About This Item
Linear Formula:
(CH3)3SiOC(=CH2)CH=CHOCH3
CAS Number:
Molecular Weight:
172.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1616761
Assay:
95%
Form:
liquid
InChI
1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+
SMILES string
CO\C=C\C(=C)O[Si](C)(C)C
InChI key
SHALBPKEGDBVKK-VOTSOKGWSA-N
assay
95%
form
liquid
impurities
2-5% 4-methoxy-3-buten-2-one
refractive index
n20/D 1.454 (lit.)
bp
68-69 °C/14 mmHg (lit.)
density
0.885 g/mL at 25 °C (lit.)
functional group
ether
storage temp.
2-8°C
Quality Level
Related Categories
General description
trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene. Mukaiyama-Michael-type addition/heterocyclization of trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky′s diene) with 1,2-diaza-1,3-butadiene has been investigated. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported.
Application
trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:
- in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins), 4H-1-aminopyrroles and 4,5H-pyrazoles
- as Diels-Alder diene for the synthesis of pyridones and pyranones
- as reagent employed in the Mannich-Michael reaction for preparation of piperidinones and enaminones
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
138.2 °F - closed cup
flash_point_c
59 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Regulatory Information
危险化学品
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M Friedrich et al.
Archiv der Pharmazie, 329(7), 361-370 (1996-07-01)
Syntheses of substituted, especially of fluoro substituted benzoxathiole 1,1-dioxides, are described. These derivatives were transformed via the Peterson olefination into substituted 2-alkylidene derivatives 27. Diels-Alder reactions of 27 with 1,1-dimethoxy- and 1-methoxy-3-trimethylsiloxy-1,3-butadiene (30, 32) gave sulfone analogues 31 of griseofulvin
The Journal of Organic Chemistry, 57, 4444-4444 (1992)
Tetrahedron, 49, 397-397 (1993)
The Journal of Organic Chemistry, 57, 3605-3605 (1992)
Mingji Dai et al.
Journal of the American Chemical Society, 129(3), 645-657 (2007-01-18)
The paper describes the course of cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups. Consistently, it was found that in the enyne cases the Diels-Alder reaction occurred specifically at the acetylenic center. Furthermore, it was
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