I've been known to build the odd one or two Cleveland with 302 Cleveland closed chamber heads. Actually I've built that combination many times in all forms from tow vehicles to street, street/strip to all out race engines from drags to circuit and even burnout engines. Flat tops, dish tops and even domes, stock stroke, increased stroke, decreased stroke, wet sump, dry sump and running on pump, avgas, LPG or even methanol, with all sorts of carb/s and intake set ups. In fact years ago the main staple of high performance Clevelands here in Australia were 2V cc headed engines as 4V heads were hard to get hold of and expensive, plus all the magazines back then were telling everybody that the 2V heads were heaps better, unless being an all out drag engine, lol. In fact I remember a magazine article over 25 years ago (would have it hidden in my junk somewhere) where they asked some of the best engine builders in the country about Cleveland builds. All but one said the 2V heads were the only way to go, the one that said 4V's is a very renowned Sprintcar and circuit engine builder and one I trusted his word back then, plus my old boss knew him as he use to build Sprintcar engines as well, back in NZ. We had a good formula for street, street/strip Cleveland builds from when I started as an apprentice in the late 80's and kept developing more power as time went on. There's still quite a few decent HP factory cast iron 2V headed engines running around over here in the high 600 to mid 700 HP naturally aspirated, but as aluminium heads become more affordable people are moving away from factory cast iron heads to the better flowing aluminium heads of CHI, AFD and Scott Cook (3V/ 4V style only on the SC) but there's those that still love seeing how far they can get with them.
As for detonation, well fuel plays only one part in the overall scheme of things. Tuning and things like spark plug heat ranges and ignition curves as well as getting you carb right is what helps with detonation. We have 98 Ron octane rated fuel over here which is roughly your 94 and there's plenty of 11:1 and even higher compression cast iron engines 2V engines running on it without detonation issues. There's a lot more 2V headed street engines over here than all the other heads combined. One of the main reasons are price, personally I've never paid more than $50 for a virgin pair of 302 2V heads, in fact I'll hunt down a complete virgin 302 Cleveland for $150-$200 as stock bore Cleveland blocks are getting harder to find. Another old trick was using 302C rods and Pistons to suit. I've personally never had a detonation issue with any Cleveland engine be it 2V or 4V open or closed chamber, get the tuning right and you should not have any problems.
As for dynamic compression ratio, that's an interesting subject that seems to be getting more confusing than answers. I belong to another (small) forum which contains a lot of different engine people from a wide variety of back grounds (not just racing) which was formed as they wanted somewhere to discuss and share ideas without the "know alls" getting involved and having nothing constructive to say (no arguments which I love) In fact that site and this one are the only ones I really post up on as the other ones I look at are full of know alls, know F alls. I have actually had been thinking of DCR lately and a discussion had already started on that site when I went on for a look one night. Unfortunately I can not say too much about any of the discussions on that site (one of their stipulations) but one thing that did come from it that I can't see a problem with mentioning was, if DCR is the be all and end all on engines performing, than how did the muscle car engines back then manage to run without dramas. These were fairly high comp engines with smallish (by today's standards) camshafts and also where's the factory data on DCR's. There is none only static compression ratios. To be honest I'm still on the fence with it, but some of the discussion on it is very enlightening to say the least and has really got me thinking. One thing though was years ago building engines we never thought of DCR and knew what static comp you could get away with Super lead fuels (as we had it here until the end of 95) and what sort of cam it took to be suitable for the build. Look at cam catalogues and their cam recommendations state what static compression ratio is needed, not what DCR it's going to give you. Even when I fully understood what DCR is, I still bring it up on the high side or even over where it's not supposed to be suitable and have managed to have the engines run great without detonation issues. I'd really love to be able to post up what's been discussed on there, but I like being on there too much to loose it, plus the bloke that nominated me to be on there would really be pissed at me.
So yeah, I've built hundreds of flat top piston with single valve relief, 2V cc headed Cleveland engines over the last near 30 years, of all types and detonation has never been a problem when everything is sorted. In saying that too, my 2V cc engines have never had an unmodified combustion chamber either, as they need some reworking to get the most out of them, but compression has still been at 10.5:1 minimum. Also they've all had some reworking in the intake throats as a minimum and on the bigger HP stuff the ports are also done, but don't increase the port size. Intake vales are no bigger than a 2.070 and exhaust valves are standard 2V 1.65 with only the short side radius needing any work on the exhaust ports. Anything else I can help with, just ask or PM me.