Configure IIS to send email from another IP

TLS just enables encryption on the smtp session and doesn't directly affect whether or not Postfix will be allowed to relay a message.

The relaying denied message occurs because the smtpd_recipient_restrictions rules was not matched. One of those conditions must be fulfilled to allow the message to go through:

smtpd_recipient_restrictions =
    permit_sasl_authenticated
    check_recipient_access hash:/etc/postfix/filtered_domains
    permit_mynetworks
    reject_unauth_destination

To explain those rules:

permit_sasl_authenticated

permits authenticated senders through SASL. This will be necessary to authenticate users outside of your network which are normally blocked.

check_recipient_access

This will cause postfix to look in /etc/postfix/filtered_domains for rules based on the recipient address. (Judging by the file name on the file name, it is probably just blocking specific domains... Check to see if gmail.com is listed in there?)

permit_mynetworks

This will permit hosts by IP address that match IP ranges specified in $mynetworks. In the main.cf you posted, $mynetworks was set to 127.0.0.1, so it will only relay emails generated by the server itself.

Based on that configuration, your mail client will need to use SMTP Authentication before being allowed to relay messages. I'm not sure what database SASL is using. That is specified in /usr/lib/sasl2/smtpd.conf Presumably it also uses the same database as your virtual mailboxes, so you should be able enable SMTP authentication in your mail client and be all set.

If you're going to be sending email directly from the IIS SMTP server, then you don't need to configure any relay settings. The server sending outbound email from itself is not a relay. The tests you're running are exactly what you should expect when trying to send email through the server from another host (because relaying is not enabled). IIS SMTP is a fully functional SMTP server, and as such, requires no relay configuration unless other hosts will be sending email through it to external domains (domains not native to the IIS SMTP server). Again, if the IIS SMTP server will be sending email from itself to external domains, no relay configuration is required.