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Ethyl 2-(triphenylphosphoranylidene)propionate

Catalog Number
ACM5717373
Product Name
Ethyl 2-(triphenylphosphoranylidene)propionate
Structure
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CAS
5717-37-3
  • Product Overview
  • Usage
Synonyms
(Carbethoxyethylidene)triphenylphosphorane; (1-Ethoxycarbonylethylidene)triphenylphosphorane
IUPAC Name
ethyl 2-(triphenyl-lambda5-phosphanylidene)propanoate
Molecular Weight
362.41
Molecular Formula
C23H23O2P
Canonical SMILES
CCOC(=O)C(=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C;
InChI
KZENFXVDPUMQOE-UHFFFAOYSA-N
InChI Key
InChI=1S/C23H23O2P/c1-3-25-23(24)19(2)26(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18H,3H2,1-2H3
Melting Point
193-195 °C(lit.)
Purity
98%
Appearance
Solid
Storage
0-6°C
Complexity
454
Covalently-Bonded Unit Count
1
EC Number
227-215-4
Exact Mass
362.144g/mol
H-Bond Acceptor
2
Heavy Atom Count
26
Isomeric SMILES
CCOC(=O)C(=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C
Monoisotopic Mass
362.144g/mol
NSC Number
76468
Rotatable Bond Count
6
Topological Polar Surface Area
26.3A^2
Application
Ethyl 2-(triphenylphosphoranylidene)propionate is a versatile yellow crystalline powder that serves as a crucial raw material and intermediate in various fields, including organic synthesis, pharmaceuticals, and agrochemicals. This compound acts as a Horner-Wadsworth-Emmons reagent, playing a key role in olefination processes. Furthermore, it is instrumental in the synthesis of more complex compounds, such as the (29S,37S)-isomer of malevamide E, known for its potent ion-channel inhibition properties.
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