I've played a map with 2 jails (specific to each team). The map name is not coming to me (Loial used to put it on I believe), but it is definitely possible to have team specific jails.
Edit: "routez"
Edit: Looking at a 'info_player_deathmatch' entity, it seems like you would just make a normal player spawn with the correct team colour and add 'jail 1' to the variables of the entity.
eg.
Entity:
info_player_deathmatch
Variables:
'teamnumber' set to '1' <---- Sets the team colour.
'GiveGun' set to 'carbine' <---- Spawn with carbine.
'GiveHopper' set to '200' <---- Spawn with 200 hopper.
'GiveAmmo' set to '200' <---- Spawn with 200 ammo.
'GiveBarrel' set to 'Chrome' <---- Spawn with chrome barrel.
'GiveCO2' set to '40oz' <---- Spawn with unloaded 40oz CO2.
'LoadedCO2' set to '20oz' <---- Spawn with loaded 20oz CO2.
'jail' set to '1' <---- Sets the spawn to a jail spawn.
(Off the top of my head)