Dipole moment on the microscopic scale and dielectric constant on the macroscopic are highly related, but there are exceptions. How are they related? Are there any classic readings on this question?
Tamar Schlick, Molecular Modeling and Simulation: An Interdisciplinary Guide (2nd edition). Springer New York Dordrecht Heidelberg London (2010). p 292 Dielectric Function.
Attached is a one-page summary of the concepts that I use in my lecture notes. The insight is to consider each in terms of a response to an electric field. The response is electronic, ionic, or molecular polarization (charge separation). The fundamental is driven by molecular polarizability. The macroscopic is driven by bulk dielectric constant. One exception to an otherwise "direct" relationship may be likely when local electric fields are not homogeneous.
Some information about the relation of the dielectric constant with the dipole moment you can find in the classical textbook: C. Kittel. Introduction to solid state physics. Chapter 13.