440868
(R)-(+)-3-Chlorostyrene oxide
98%
Synonym(s):
(R)-(+)-(3-Chlorophenyl)oxirane
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About This Item
Empirical Formula (Hill Notation):
C8H7ClO
CAS Number:
Molecular Weight:
154.59
UNSPSC Code:
12352000
MDL number:
assay
98%
optical activity
[α]20/D +21°, neat
refractive index
n20/D 1.551 (lit.)
bp
67-68 °C/1 mmHg (lit.)
density
1.214 g/mL at 25 °C (lit.)
SMILES string
Clc1cccc(c1)[C@@H]2CO2
InChI
1S/C8H7ClO/c9-7-3-1-2-6(4-7)8-5-10-8/h1-4,8H,5H2/t8-/m0/s1
InChI key
YVMKRPGFBQGEBF-QMMMGPOBSA-N
Application
Key chiral synthon for the preparation of the potent antidiabetic and antiobesity agent CL-316,243, a benzodioxole-containing phenethanolamine. Ring opening of this chiral epoxide with amines produces amino alcohols which have been used as β-adrenergic agonists.
Reactant involved in:
- Diastereoselective Wadsworth-Emmons cyclopropanation for synthesis of quaternaty cyclopropyl esters
- Synthesis of phenylethanolamine derivatives as β3-adrenergic receptor agonists
- Stereoselective ring-opening for synthesis of β-aryloxy-substituted alcohols and amines
- Synthesis of Biphenyl benzoic acid derivatives as β3-adrenergic receptor agonists
- Synthesis of (S)-2-, 3-, and 4-chlorostyrene oxides with epoxide hydrolase
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D. Badone et al.
Bioorganic & Medicinal Chemistry Letters, 16, 1921-1921 (1994)
Disodium (R,R)-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-amino] propyl]-1,3-benzodioxole-2,2-dicarboxylate (CL 316,243). A potent beta-adrenergic agonist virtually specific for beta 3 receptors. A promising antidiabetic and antiobesity agent.
J D Bloom et al.
Journal of medicinal chemistry, 35(16), 3081-3084 (1992-08-07)
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