CAS:4009-98-7 | (Methoxymethyl)triphenylphosphonium Chloride
Molecular Formula: C20H20ClOP
Molecular Weight:342.8
EINECS:223-664-5
Purity:98%
Package:100g/250g/500g/1kg/5kg/10kgbulk package
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Product Introduction
Name | (Methoxymethyl)triphenylphosphonium chloride |
MDL No | MFCD00011800 |
Melting point | 185-195 °C (dec.)(lit.) |
Flash Point | >250°C |
Appearance | White to grey powder or crystals |
Sensitivity | Hygroscopic |
Solubility (soluble in) | Chloroform (Slightly), Methanol (Slightly) |
Storage condition | Store at 10°C - 25°C |
InChI | InChI=1S/C20H21OP/c1-21-17-22(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-16,22H,17H2,1H3 |
InChIKey | SJFNDMHZXCUXSA-UHFFFAOYSA-M |
Smiles | COC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-] |
Applications:
(Methoxymethyl)triphenylphosphonium chloride(CAS:4009-98-7) is used as a phase transfer catalyst and in the synthesis of taxol-A fragment. It is widely used in the synthesis of pharmaceutical product cephalotaxine, which is used as an antiviral and antitumor agent.
References:
Wittig reaction (see Appendix 1) of the derived phosphorane with aldehydes and ketones gives enol ethers, readily hydrolyzed to homologous aldehydes. For an example (adamantanone to adamantanecarboxaldehyde), see: Chem. Ber., 95, 2514 (1962). For use of the reaction in the synthesis of hydroisoquinoline AMPA antagonists, see: J. Med. Chem., 39, 2219 (1996). Reaction with chiral 2,3-epoxyaldehydes provides an enantioselective synthesis of (E)-4-hydroxyalkenes: J. Chem. Soc., Chem. Commun., 232 (1993).
Lee, K.; Poudel, Y. B.; Glinkerman, C. M.; Boger, D. L. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs. Tetrahedron 2015, 71 (35), 5897-5905.
Yu, Q.; Ma, S. An Enantioselective Synthesis of (R)-5,6-Octadecadienoic Acid. Eur. J. Org. Chem. 2015, 2015 (7), 1596-1601.
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