217166
1-Methoxy-1,3-cyclohexadiene
technical grade, 65%
Synonym(s):
2,3-Dihydroanisole
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About This Item
Empirical Formula (Hill Notation):
C7H10O
CAS Number:
Molecular Weight:
110.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
218-483-3
MDL number:
InChI key
LNRUJSUKKBJFOM-UHFFFAOYSA-N
InChI
1S/C7H10O/c1-8-7-5-3-2-4-6-7/h2-3,5H,4,6H2,1H3
SMILES string
COC1=CC=CCC1
grade
technical grade
concentration
65%
refractive index
n20/D 1.488 (lit.)
bp
40 °C/15 mmHg (lit.)
density
0.929 g/mL at 25 °C (lit.)
General description
1-Methoxy-1,3-cyclohexadiene is a useful Diels-Alder diene employed in Diels-Alder cycloadditions. It undergoes Diels-Alder reaction with alkyne to yield anisole derivative.
Application
1-Methoxy-1,3-cyclohexadiene was used in the following studies:
- Synthesis of tetracyclic polyhydroxyquinones via Diels-Alder reaction.
- Synthesis of tetra-ortho-substituted biaryls via Diels-Alder reaction.
- Synthesis of optically active form of dihydroisocoumarin fragment of the gastroprotective natural product AI-77-B, via regiospecific Diels-Alder reaction with an acetylenic ester derivative.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
80.6 °F - closed cup
flash_point_c
27 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Bradley O Ashburn et al.
Journal of the American Chemical Society, 129(29), 9109-9116 (2007-07-03)
The application of the Diels-Alder approach to biaryls (DAB) is described for the synthesis of tetra-ortho-substituted biaryl compounds containing orthogonally functionalized substituents. The syntheses of phosphorus-containing, disubstituted alkynes and carbonyl-containing, disubstituted alkynes were accomplished in two to three steps from
Bradley O Ashburn et al.
Organic & biomolecular chemistry, 6(2), 255-257 (2008-01-05)
A series of nitrophenyl acetylenes were evaluated for their utility in a cycloaddition-cycloreversion approach to polysubstituted biaryls. ortho-Nitrophenyl acetylene consistently provided the target biaryls in superior yields as compared to the meta and para nitro substituted variants.
M. Carmen Carreño et al.
The Journal of organic chemistry, 61(18), 6136-6138 (1996-09-06)
The synthesis of tetracyclic polyhydroxyquinones 5a and 5b was achieved through a sequence involving two Diels-Alder reactions with 1-methoxy-1,3-cyclohexadiene: the first with 2-(p-tolylthio)naphthazarin and the second on the resulting tricyclic derivative previously transformed into a (p-tolylsulfinyl)naphthazarin. The success of this
Stereoselective synthesis of dihydroisocoumarin moiety of microbial agent AI-77-B: a Diels-Alder based strategy.
Ghosh AK and Cappiello J.
Tetrahedron Letters, 39(48), 8803-8806 (1998)
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