Do any Greek texts discuss Jewish monotheism? Do any pre-Roman Jewish texts discuss Greek philosophy?
Because both peoples had an exceptionalist attitude toward themselves, I'm interested in how they may have viewed each other.
There isn't as much surviving Jewish text from the period of the Golden Era of Greece as you might expect. There's a ton we don't know about what was going on in Judaism at that point, and much of what we do know/suspect comes from later sources that may or may not be historically accurate.
The book the Wisdom of Sirach (aka Ben Sira or Ecclesiasticus) has sometimes been described as responding to/influenced by Stoic Philosophy, but that's debated.
The First Book of the Maccabees, which is basically propoganda, talks about some of the problems that the Maccabees had with Hellenistic culture, but I wouldn't describe it as philosophically engaged and probably isn't what you're looking for. The Second Book of the Maccabees has a more theological take and might be of some interest, but is at the very end of the time period you're interested in.
There was a tradition, recorded in Josephus and I Maccabees, that the Jews and the Spartans were somehow related. Both include letters sent between Jewish and Spartan leaders to this effect around the time of the Maccabean revolt.
These sources were both written long after Alexander's time and the letters recorded in these sources may be fraudulent, but it's interesting that the tradition existed at all. They show that Jews at the time were interested in showing a connection between themselves and one particular Greek city.
That's about all I can think of on this score. You'll find a ton of writings by each group about the other from the Hellenistic and Roman periods, but nothing earlier that I can recall.