Which books in the Catholic Old Testament, precede the canonisation of the Hebrew Bible?

Which books in the Catholic Old Testament, precede the canonisation of the Hebrew Bible? I understand for example that the *Books of Maccabees* is not part of the Hebrew Bible Canon, but from what I heard, it follows it in time, rather than being rejected from it. So it wouldn't precede it. I know that the Protestant Old Testament Canon is the same one as Jews use today in their Hebrew Bible, and that the Catholic Old Testament Canon has all that plus extra books. So I am wondering if any books in the Catholic Old Testament are so old in origin that they precede the canonisation of the Hebrew Bible / canonisation of the Hebrew Bible used today (which is in the masoretic tradition)? There is a complexity here also, but one that opens up a possible avenue that help address the question. The Septuagint is so old it even precedes Christianity, and it has a number of books not in the modern Hebrew canon. And furthermore, my understanding is that one skilled in biblical hebrew, and ancient greek, that studies the Septuagint carefully, sees that the underlying text it is translating is slightly different in some places, implying that there was a Hebrew version for it. Further backing that up, my understanding is that in the Judean desert, while there's lots of uniformity, (and particularly uniformity within the Torah), still there are different versions/variations of text for various Hebrew books of the bible, in places here and there, small variations. And it has been viewed(perhaps by Emmanuel Tov?), as there being hebrew proto-septuatint and (of course hebrew), proto-masoretic. Moving from that to books. If there were Hebrew proto-masoretic books not in the masoretic canon of today then perhaps we wouldn't know. But it'd be interesting to know if there are Hebrew proto-septuagint books in the Dead Sea Scrolls / Scrolls from the Judean Desert? And perhaps some of those books in Greek form might be in the catholic bible, so would fit what I am asking of any books in the Catholic Bible that precede the canonization of the Hebrew Bible. But perhaps even without considering the DSS/scrolls of the Judean desert, there might be an answer to if any books of the Catholic Old Testament are known to precede canonization of the Hebrew Bible used today?