494127
Benzyl 3-pyrroline-1-carboxylate
90%
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About This Item
Empirical Formula (Hill Notation):
C12H13NO2
CAS Number:
Molecular Weight:
203.24
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
InChI
1S/C12H13NO2/c14-12(13-8-4-5-9-13)15-10-11-6-2-1-3-7-11/h1-7H,8-10H2
SMILES string
O=C(OCc1ccccc1)N2CC=CC2
InChI key
XSKKIFJNZPNVGO-UHFFFAOYSA-N
assay
90%
refractive index
n20/D 1.544 (lit.)
bp
133-137 °C/0.6 mmHg (lit.)
density
1.132 g/mL at 25 °C (lit.)
General description
Benzyl 3-pyrroline-1-carboxylate, also known as N-benzyloxycarbonyl 3-pyrroline, is an N-substituted 3-pyrroline. Its enthalpy of vaporization at boiling point has been evaluated. Its epoxidation using m-chloroperbenzoic acid (m-CPBA) has been reported.
Application
Benzyl 3-pyrroline-1-carboxylate (N-Benzyloxycarbonyl 3-pyrroline) may be used to prepare (+)(3R,4R)-3,4-dihydroxy pyrrolidine via enantioselective trans-dihydroxylation catalyzed by frozen/thawed cells of Sphingomonas sp. HXN-200.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Asymmetric trans-dihydroxylation of cyclic olefins by enzymatic or chemo-enzymatic sequential epoxidation and hydrolysis in one-pot.
Xu Y, et al.
Green Chemistry, 13(9), 2452-2458 (2011)
Yaws CL.
Thermophysical Properties of Chemicals and Hydrocarbons, 598-598 (2014)
Dongliang Chang et al.
The Journal of organic chemistry, 68(22), 8599-8606 (2003-10-25)
The bacterial strain Sphingomonas sp. HXN-200 was used to catalyze the trans dihydroxylation ofN-substituted 1,2,5,6-tetrahydropyridines 1 and 3-pyrrolines 4 giving the corresponding 3,4-dihydroxypiperidines 3 and 3,4-dihydroxypyrrolidines 6, respectively, with high enantioselectivity and high activity. The trans dihydroxylation was sequentially catalyzed
David R Williams et al.
Journal of the American Chemical Society, 126(11), 3434-3435 (2004-03-18)
A powerful cascade reaction process for the construction of functionalized cis-bicyclo[3.3.0]octenes has been developed. Carbolithiation of 3-methylene-1,4-cyclooctadiene with 1 degrees , 2 degrees , or 3 degrees alkyllithium reagents leads to cyclooctadienyl anions, which undergo disrotatory electrocyclization and subsequent trapping
S L Gwaltney et al.
Bioorganic & medicinal chemistry letters, 11(7), 871-874 (2001-04-11)
Sulfonate analogues of combretastatin A-4 have been prepared. These compounds compete with colchicine and combretastatin A-4 for the colchicine binding site on tubulin and are potent inhibitors of tubulin polymerization and cell proliferation. Importantly, these compounds also inhibit the proliferation
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