Trabalhando AppleScript:
on deleteTrack(trackName)
tell application "iTunes"
set theTrack to track named trackName of playlist "Library"
set songFile to location of theTrack
delete theTrack
end tell
tell application "Finder" to delete songFile
end deleteTrack
on run
tell application "iTunes"
set currentSong to name of current track
end tell
deleteTrack(currentSong)
end run
Testado e confirmado para trabalhar em músicas atualmente sendo reproduzidas sem problemas.
Acredite no link para excluir o código AppleScript.