422436

Sigma-Aldrich

Methyl 1-cyclopentene-1-carboxylate

97%

Linear Formula:
C5H7CO2CH3
CAS Number:
Molecular Weight:
126.15
Beilstein/REAXYS Number:
2040162
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

97%

refractive index

n20/D 1.4660 (lit.)

bp

76-78 °C/9 mmHg (lit.)

density

1.031 g/mL at 20 °C (lit.)

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.

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.

Packaging

1, 10 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

WGK Germany

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

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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