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About This Item
Linear Formula:
C5H7CO2CH3
CAS Number:
Molecular Weight:
126.15
Beilstein/REAXYS Number:
2040162
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
assay
97%
form
liquid
refractive index
n20/D 1.4660 (lit.)
bp
76-78 °C/9 mmHg (lit.)
density
1.031 g/mL at 20 °C (lit.)
functional group
ester
SMILES string
COC(=O)C1=CCCC1
InChI
1S/C7H10O2/c1-9-7(8)6-4-2-3-5-6/h4H,2-3,5H2,1H3
Inchi Key
VTYCAXIAUKEGBQ-UHFFFAOYSA-N
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General description
Methyl 1-cyclopentene-1-carboxylate, a cyclic alkene, is a cyclopentene derivative. It participates in the synthesis of azulene derivatives by initially forming the corresponding cyclopropanol followed by oxy-Cope rearrangement.[1]
Application
Methyl 1-cyclopentene-1-carboxylate may be used as starting material in the synthesis of pinnaic acid and halichlorine.[2] It undergoes asymmetric oxidative Heck reaction with aryl boronic acids to form coupling products in the presence of chiral NHC (N-heterocyclic carbine)-palladium (II) complex.[3]
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
143.6 °F - closed cup
flash_point_c
62 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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Rodrigo B Andrade et al.
Organic letters, 7(25), 5733-5735 (2005-12-03)
[chemical reaction: see text]. Concise formal syntheses of marine alkaloids (+/-)-pinnaic acid (1) and (+/-)-halichlorine (2) have been accomplished from a common intermediate. The syntheses illustrate the utility of selective olefin cross metathesis methodologies for the elaboration of advanced synthetic
THE ORGANIC CHEMISTRY NOTEBOOK SERIES, A DIDACTICAL APPROACH,?(I) A THEORETICAL MECHANISTIC APPROACH TO DIASTEROSELECTIVE SYNTHESIS OF CIS-1, 2-DIALKENYLCYCLOPROPANOLS AND SUBSEQUENT OXY-COPE REARRANGEMENT BY JIN KUN CHA ET AL.
Bravo J.
Revista Boliviana de Quimica, 22(1), 1-10 (2005)
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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