422436
Methyl 1-cyclopentene-1-carboxylate
97%
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About This Item
Linear Formula:
C5H7CO2CH3
CAS Number:
Molecular Weight:
126.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2040162
Product Name
Methyl 1-cyclopentene-1-carboxylate, 97%
InChI
1S/C7H10O2/c1-9-7(8)6-4-2-3-5-6/h4H,2-3,5H2,1H3
SMILES string
COC(=O)C1=CCCC1
InChI key
VTYCAXIAUKEGBQ-UHFFFAOYSA-N
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
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Application
Methyl 1-cyclopentene-1-carboxylate may be used as starting material in the synthesis of pinnaic acid and halichlorine. 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.
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.
Storage Class
10 - Combustible liquids
wgk
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)
Regulatory Information
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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)
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
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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