Preheat the oven to 375ºF. Butter the sides and bottom of a 9x13 glass or light-colored metal baking pan. Set aside.
Place the chocolate chips in a small bowl and toss them with the bourbon until covered. Sprinkle 2 tablespoons of flour over the chips and toss until coated. Set aside.
Place the oats and cubed butter in a large bowl. Pour the boiling water over the oat mixture, wait 30 seconds, and stir to moisten all the oats and melt the butter. Set the mixture aside for 25 to 30 minutes to allow it to cool.
In a separate bowl, whisk together the both sugars, eggs, baking soda, baking powder, and cinnamon until combined. Fold in the cooled oatmeal and stir until well combined. Gently fold in the remaining flour and then the chocolate chips. Pour the batter into the prepared pan and smooth out the top.
Bake the cake for 35-45 minutes or until a toothpick inserted in the center comes out clean.
Let the cake cool in the pan on a wire rack for at least 30 minutes.
Cinnamon Cream Cheese Frosting
In the bowl of a standing mixer fitted with the paddle attachment, beat the butter until completely smooth. Add the cream cheese and beat until combined. Add the powdered sugar, vanilla, and cinnamon and beat until smooth, about 1 minute. Cover the bowl tightly and refrigerate for at least 30 minutes.
Spread a thin, even layer of frosting over the cooled cake. Chill it for 15 minutes so that it can set. Slice and serve. The frosted cake will keep, refrigerated and tightly covered, for up to 3 days. Bring the cake back to room temperature before serving.