Dibenzyl chloroMethyl phosphate

China [CN]

I. Basic Information

Chinese Name: Dibenzyl chloromethyl phosphate

English Name: Dibenzyl chloromethyl phosphate

CAS Number: 1080-35-3

Molecular Formula: C₁₅H₁₆ClO₄P

Molecular Weight: 326.71 (Calculated: C 55.14%, H 4.93%, Cl 10.85%, O 19.59%, P 9.49%)

II. Chemical Structure and Characteristics

Structural Analysis: This molecule is an organophosphate derivative, with a core phosphate group (-PO₄-), two of which are benzyloxy groups (-OCH₂Ph, where Ph represents a phenyl group), and a third substituent is a chloromethyl group (-CH₂Cl). Core Features:

The phosphate structure imparts stability and polarity to the molecule, while the two benzyl groups (-CH₂Ph) enhance lipid solubility through the hydrophobic interaction of the benzyl ring.

The chlorine atom in the chloromethyl group (-CH₂Cl) has a high leaving ability and serves as the primary nucleophilic reaction site. Reactivity is regulated by the electron-withdrawing effect of the phosphate group.

The presence of the benzyl group enhances solubility in aromatic solvents and facilitates subsequent deprotection (e.g., hydrogenolysis to remove the benzyl group).