Puoi utilizzare un generatore di righe Oracle :
insert into your_table ( your_column )
select
to_date('2000/01/01', 'yyyy/mm/dd') + N.n
from
(SELECT ROWNUM n
FROM ( SELECT 1 just_a_column
FROM dual
CONNECT BY LEVEL <=
SYSDATE
- to_date('2000/01/01', 'yyyy/mm/dd')
+ 1
) T
) N
where
to_date('2000/01/01', 'yyyy/mm/dd') + N.n <= SYSDATE