466433
1-Acetyl-1-cyclopentene
97%
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About This Item
Linear Formula:
C5H7COCH3
CAS Number:
Molecular Weight:
110.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
InChI
1S/C7H10O/c1-6(8)7-4-2-3-5-7/h4H,2-3,5H2,1H3
SMILES string
CC(=O)C1=CCCC1
InChI key
SLNPSLWTEUJUGY-UHFFFAOYSA-N
assay
97%
refractive index
n20/D 1.483 (lit.)
bp
70 °C/20 mmHg (lit.)
density
0.955 g/mL at 25 °C (lit.)
functional group
ketone
General description
1-Acetyl-1-cyclopentene is a cyclic alkene. Its lithium enolate undergoes Brook rearrangement-mediated [3+4] annulation with 3-alkyl-3-haloacryloylsilanes to afford tricyclo[5.3.0.01,4]decenone derivatives. Asymmetric oxidative Heck reaction of 1-acetyl-1-cyclopentene in the presence of a Pd-ligand has been reported.
Application
1-Acetyl-1-cyclopentene may be used in the preparation of the following allenylcycloalkanes:
- 1-vinylidenyl-2-[4-(trimethylsilyl)-3-butynyl]-cyclopentane
- 1-vinylidenyl-2-(3-butynyl)-cyclopentane
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B Green et al.
Steroids, 59(8), 479-484 (1994-08-01)
The addition of diphenylnitrilimine and C-o-chlorodiphenylnitrilimine to 3 beta-hydroxyandrost-5,16-diene (3b) produced a 1/1 ratio of regioisomeric, 1,3-diaryl-2-pyrazolines (6a, 7a and 6b, 7b), whereas the addition of N-o-chlorodiphenylnitrilimine gave a 5/1 ratio in favor of the [17 alpha, 16 alpha-d] regioisomer
Facile Construction of a Tricyclo [5.3. 0.01, 4] decenone Ring System by the Brook Rearrangement-Mediated [3+4] Annulation.
Takeda K and Ohtani Y.
Organic Letters, 1(4), 677-680 (1999)
An intramolecular allenic [2+ 2+ 1] cycloaddition.
Brummond KM, et al.
The Journal of Organic Chemistry, 63(9), 6535-6545 (1998)
Kyung Soo Yoo et al.
The Journal of organic chemistry, 75(1), 95-101 (2009-12-04)
Chiral dimeric tridentate NHC-amidate-alkoxide palladium(II) complexes, 3a and 3b, effected oxidative boron Heck-type reactions of aryl boronic acids with both acyclic and cyclic alkenes at room temperature to afford the corresponding coupling products with high enantioselectivities. The high degree of
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