In Rick Sternbech's 1979 book "The Space Flight Chronology", which elaborated on TOS plus some of the gaps in the TOS history, Earth's first interstellar flight and first contact was with an anti-matter spiked fusion starship called the Icarus when it travelled to Alpha Centurai. The Icarus had a maximum speed of 0.85c.
Transporters capable and safe enough to transmit lifeforms appear pretty much exactly the year specified in SFB and by Geordi LaForge TNG. Before then only inanimate objects could be transported. Cargo transporters had existed at least 20 to 30 years before the date given in in "The Space Flight Chronolgy".
Other key TSFC events are:
United Nations establishes The Solar Fleet to operate space craft for search and rescue, exploration and protection of the Sol solar system.
The UN launches Fusion Torch sublight starship missions to Tau Ceti and Alpha Centurai.
Practical Warp Drive technology invented by Zeffram Cochrane. The original theories of Warp Drive date back to 1956.
UNSS Bon Adventure launched as Earth's first Warp Drive starship.
UNSS Bon Adventure lost on third deep space mission to Barnard's Star.
Vulcans are first contacted after the Earth Fusion Warp starship UNSS Amity rescues a stricken Vulcan starship.
The Federation is loosely founded a year before the start of the Romulan War. It is more of an association similar to Earth's European Union and for mutual protection. Members retain their own navies for a while whilst resources and technology are pooled to design newer starships for a common Federation navy.
Earth develops rudimentary deflector shield technology but only has one class of destroyers equiped with it when the Romulan War starts. Ironically the first starship lost is one of these Marshall Class destroyers.
Romulan War breaks out after a Romulan successful "Pearl Harbour" style attack on Earth's original Starbase / Deep Space One by 14 Romulan warships.
The attack is launched from covert bases established over many years throughout Earth, Vulcan, Andorian and Tellarite space.
The Romulans subsequently declare war on Vulcan, Andor and Tellar.
Most of Earth's poorly armed Fusion Warp Drive starships have armour, hull cooling and simple electromagnetic forcefields to deflect cosmic radiation and particle beams only. The Romulans slaughter them in many of the early space battles.
The first Federation built starship is a cruiser USS Horizon NCC-01. Six are built. It is the first starship in the Federation equiped with MAM Warp Drive and Impulse Power for sublight maneuvering. The increased power levels allow it to host a formidable arsenal of Laser and Particle Beam Cannons plus protection from attack by improved Deflector Shields and hull energy dispersion panels. It totally outclasses all previous Earth and Romulan warships. It proves decisive in forcing the conclusion of the Romulan War.
A prototype state of the art battlecruiser is constructed, tested and then mothballed never to enter service. Its improvements become the main features of a subsquent later cruiser design. The prototype battlecruiser closely resembles the Daedalus class exploration cruiser in layout, so presumably the mentioned cruiser was the Daedalus class.
The Klingon Empire is first contacted around the same time as in SFB when a Federation exploration starship is attacked by a Klingon battlecruiser in what was later realised to be Klingon space. This is the root of all Klingon claims of Federation expansionism and future hostilies.
The USS Moscow, a Baton Rouge class heavy cruiser, become the first Federation starship to be equiped with transporters capable of beaming lifeforms safely.
The books history ends with the launch of the Constitution Class heavy cruisers.
TSFC weapons technology for Earth / Federation:
Lasers -> Laser Cannons -> Laser Bank -> Phaser Bank.
Particle Beam -> Particle Beam Cannon (Disrupters were never developed by the Federation).
Attomic Missile -> Fusion Torpedo -> Photon Torpedo.
Sublight propulsion systems technology for Earth / Federation:
Chemical -> Fission -> Fusion Torch -> Anti-Matter Spiked Fusion Torch -> Ion -> Impulse Power.
Warp Drive technology:
Fusion Warp drive -> MAM warp Drive -> Dilithium Focus MAM Warp Drive.
As Rick Sternbech was involved with both TOS and TNG I've always tended to regard his work nearer to canon than the usual fanon. Much of the ADB timeline parallels his version of Star Trek history.
The Michael Okuda book, though based on more on episode canon and the author also having equal involvement in TNG, does have a few mistakes when compared to actual episodes.
ENT does contradict quite a few things in TOS and TNG especially regarding transporters and Klingon first contact.
ENT is good entertainment with all the politically correct namby pambism that pollutes Voyager removed. However, there are moments and technology that drift totally off course regarding Star Trek canon timeline.