213306
苯基乙烯基亚砜
95%
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线性分子式:
C6H5SOCH=CH2
化学文摘社编号:
分子量:
152.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
243-831-6
Beilstein/REAXYS Number:
2039218
MDL number:
产品名称
苯基乙烯基亚砜, 95%
InChI key
MZMJHXFYLRTLQX-UHFFFAOYSA-N
InChI
1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2
SMILES string
C=CS(=O)c1ccccc1
assay
95%
form
liquid
refractive index
n20/D 1.585 (lit.)
bp
93-95 °C/0.2 mmHg (lit.)
density
1.139 g/mL at 25 °C (lit.)
functional group
sulfoxide
storage temp.
2-8°C
Quality Level
Gene Information
human ... LOC129293(129293)
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General description
Phenyl vinyl sulfoxide reacts with lithium enolates of ketones at -78°C in THF to yield bicyclo[n.2.0]alkan-1-ols. It also reacts with in situ generated (dialkylamino)magnesium reagent to yield symmetrical β-(dialkylamino)dithioacetals. It participates as an acetylene equivalent in Diels-Alder reactions.
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions.
Paquette LA, et al.
Journal of the American Chemical Society, 100(5), 1597-1599 (1978)
Masataka Kawakita et al.
The Journal of organic chemistry, 62(23), 8015-8017 (2001-10-24)
Vinyl sulfoxides (PhSOCR(1)=CHR(2): R(1) = H, Me, or Ph; R(2) = H or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines (R(3)R(4)NH: R(3) = Et, i-Pr, or Bn; R(4) = Me
X Ji et al.
Acta crystallographica. Section B, Structural science, 45 ( Pt 1), 93-99 (1989-02-01)
Three diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder [4 + 2] cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene. The isomers were separated by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of
Wendy A Loughlin et al.
Organic & biomolecular chemistry, 1(8), 1347-1353 (2003-08-22)
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel
商品
The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.
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