Detect Ctrl-Click BoolProp #Blender

blender-detect-ctrl-click-boolprop.py

import bpy

class SimpleOperator(bpy.types.Operator):
    """Tooltip"""
    bl_idname = "object.simple_operator"
    bl_label = "Simple Object Operator"

    def invoke(self, context, event):
        ev = []
        if event.ctrl:
            ev.append("Ctrl")
        if event.shift:
            ev.append("Shift")
        if event.alt:
            ev.append("Alt")
        if event.oskey:
            ev.append("OS")
        ev.append("Click")
        
        self.report({'INFO'}, "+".join(ev))
        return {'FINISHED'}

class HelloWorldPanel(bpy.types.Panel):
    """Creates a Panel in the Object properties window"""
    bl_label = "Hello World Panel"
    bl_idname = "OBJECT_PT_hello"
    bl_space_type = 'PROPERTIES'
    bl_region_type = 'WINDOW'
    bl_context = "object"

    def draw(self, context):
        layout = self.layout
        wm = context.window_manager
        layout.prop(wm, "my_bool")


def upd(self, context):
    bpy.ops.object.simple_operator('INVOKE_DEFAULT')
       
def register():
    bpy.utils.register_class(HelloWorldPanel)
    bpy.utils.register_class(SimpleOperator)
    bpy.types.WindowManager.my_bool = bpy.props.BoolProperty(update=upd)

def unregister():
    bpy.utils.unregister_class(HelloWorldPanel)
    del bpy.types.WindowManager.my_bool

if __name__ == "__main__":
    register()

Great !! Thanks again for taking the time