212830
反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯
95%
别名:
Danishefsky 二烯
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关于此项目
线性分子式:
(CH3)3SiOC(=CH2)CH=CHOCH3
化学文摘社编号:
分子量:
172.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1616761
产品名称
反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯, 95%
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
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Application
反式 -1-甲氧基-3-三甲基硅氧基-1,3-丁二烯被用于：
- 合成灰黄霉素（sulfogriseofulvins）、4H-1-氨基吡咯和4,5H-吡唑砜类似物
- 用作合成吡啶酮 和吡喃酮的 Diels-Alder 二烯
- Mannich-Michael 反应中用于制备哌啶酮 和烯胺酮的试剂
General description
反式-1-甲氧基-3-三甲基甲硅烷氧基-1,3-丁二烯是一种官能化的Diels-Alder二烯。研究了反式-1-甲氧基-3-三甲基甲硅烷氧基-1,3-丁二烯（Danishefsky二烯）与1,2-二氮杂-1,3-丁二烯的Mukaiyama-Michael型加成/杂环化反应。已经报道了介孔无机/金属有机杂化材料催化苯甲醛与Danishefsky二烯的不对称杂Diels-Alder环化反应。
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
存储类别
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)
法规信息
危险化学品
此项目有
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
Tetrahedron, 49, 397-397 (1993)
Marie-Laure Teyssot et al.
The Journal of organic chemistry, 72(7), 2364-2373 (2007-03-10)
Electron-poor 6-oxo-1-sulfonyl-1,6-dihydropyridine-3-carboxylates 1b-d undergo cross-Diels-Alder reactions with electron-rich dienes 4a-f under hyperbaric conditions, reacting either as dienophiles to yield normal-electron-demand (NED) cycloadducts 10 and/or 11 or as dienes to give inverse-electron-demand (IED) cycloadducts 12 and/or 13. The latter are converted
The Journal of Organic Chemistry, 57, 4444-4444 (1992)
Orazio A Attanasi et al.
Organic letters, 10(10), 1983-1986 (2008-04-23)
The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky's diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4 H-1-aminopyrroles and 4,5 H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as
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