[curiouscat]

I came across this molecule during reading up some patents. Thought it might be a fun challenge for those honing their skills in  esoteric IUPAC nomenclature:



Was mighty difficult to me ; maybe you guys are smarter!

Related information on the molecule (not related to naming it):

It is a hepatobiliary imaging agent (when combined with Technetium). Decreased liver uptake is indicative of hepatocyte disease.

[discodermolide]

Well I'm not smarter but ChemDraw says it is:
xxxxxxxxxxxxxxxxxxxxxx
But I don't believe it

[curiouscat]

Well I'm not smarter but ChemDraw say it is:
XXXXXXXXXXXXX

But I don't believe it

Darn! I ought to have admonished people to stay away from those "robots". 

I can't argue with Chemraw but my source has another (only very very slightly different) name for it.  Perhaps both are right.

PS. @discodermolide: Could I request you to mask your answer for a bit? Let's give non-Chemdraw humans a shot! 

[Guitarmaniac86]

I would call it:

4-bromo-1,3,5,trimethylphenyl-2-N-(2-N,N-diethanoyl) ethanamide

[curiouscat]

I would call it:

4-bromo-1,3,5,trimethyl-2-(2-N,N-diethanoyl) ethanamide

You forgot the ring?

[Guitarmaniac86]

I would call it:

4-bromo-1,3,5,trimethyl-2-(2-N,N-diethanoyl) ethanamide

You forgot the ring?

Oops :S How silly of me!

[curiouscat]

You forgot the ring?



Oops :S How silly of me!

Could you mask the computer generated answer for a bit? Thanks!

[curiouscat]

Well I'm not smarter but ChemDraw says it is:

It funny how ChemDraw and Symex gave you two different answers. Make things messy enough and even computers don't agree apparantly. 

[discodermolide]

Look it up in ChemSpider!

[curiouscat]

Look it up in ChemSpider!

Same as what my original source had and hence different from its other two algorithmic brethren!

[orgopete]

I came across this molecule during reading up some patents. Thought it might be a fun challenge for those honing their skills in  esoteric IUPAC nomenclature:
…

Just a comment on the challenge. When I began teaching, I wrestled with what I should do with IUPAC nomenclature. I had spent a virtual career seldom using it. In the pre-computer days, compounds were identified by their nomenclature, pre 196X CAS, post 196X CAS, German, French, common, trade, etc. I guess you could include IUPAC. If compounds are identified by their names, then a single name for each compound should enable exact searching.

In the computer era, you can search by structure. The actual structure is common to all names. If you could transfer that information, the names really didn't matter. Even with IUPAC names, there are the US variants, e.g., 1-hexene rather than hex-1-ene. None the less, both are quite understandable. If you think about my initial comment, then what matters more is whether one can draw the structure from an understandable name. For example, could you draw cholesterol from its IUPAC name? If you want a challenge, try writing its IUPAC name. I argue, cholesteryl acetate or 2-chlorocholesterol are readily understandable and more chemists could draw their structures than from IUPAC names.

Personally, I think it is an interesting challenge as to whether the programmers at Cambridge Scientific can create code to interpret the IUPAC rules to create a single satisfactory IUPAC name. In what I would argue conforms with my point, I presume curiouscat either used a structural representation or a systematic derivation of a name to draw the compound in the first place. I know students are required to use IUPAC nomenclature, but one should also keep in perspective that systematic nomenclature should be the objective. I have yet to discover a textbook in which IUPAC names are used exclusively. Okay curiouscat, tell me I'm wrong and you first had to decode the IUPAC name.

[curiouscat]

I presume curiouscat either used a structural representation or a systematic derivation of a name to draw the compound in the first place. I know students are required to use IUPAC nomenclature, but one should also keep in perspective that systematic nomenclature should be the objective. I have yet to discover a textbook in which IUPAC names are used exclusively. Okay curiouscat, tell me I'm wrong and you first had to decode the IUPAC name.

Ha. Better than that. I was merely reading the Package insert for a Radiopharmaceutical when I happened to come across the IUPAC name and structure printed side by side. 

http://usa.braccoimaging.com/images/stories/pdf/nuclear/choletec/choletec-PI_8.5x11.pdf

Actually I'm quite ambivalent about the amount of emphasis on the IUPAC nomenclature in schools. I often have the same doubts you do; Is it really serving a good purpose?

PS. One of my intentions behind the "challenge" was to probe whether typical chemists are capable of IUPAC naming "real" molecules outside of the toy-examples in school. Apparently not. At least not without some software. 

[discodermolide]

You don't really ned it in an everyday chemistry job, unless you are a teacher of chemistry.
In my job I only used it when writing papers or patents. Until the advent of software the company employed a nomenclature expert, guess what they did?
Papers and patents compounds were named using IUPAC rules. So we just plugged the structure into the computer and bingo out came the name.
As to Orgopete's suggestion about the software developers at ChemDraw. I have version 12 ultra Mac version. There is a version 13 available but I have not installed that on this Mac. So they may have tweaked the code to improve the naming portion of the program.
Later I'll fire up version 13 on the other machine and make the comparison.

[curiouscat]

In my job I only used it when writing papers or patents. Until the advent of software the company employed a nomenclature expert, guess what they did?

Never knew! Guess I'm too young! 

Papers and patents compounds were named using IUPAC rules. So we just plugged the structure into the computer and bingo out came the name.
As to Orgopete's suggestion about the software developers at ChemDraw. I have version 12 ultra Mac version. There is a version 13 available but I have not installed that on this Mac. So they may have tweaked the code to improve the naming portion of the program.
Later I'll fire up version 13 on the other machine and make the comparison.

The big utility of IUPAC names was a sort of "fingerprint" to classify molecules uniquely. i.e. Has this been made before?

This depends on the existance of a unique name for each molecule and a molecule for each name. Unfortunately IUPAC seems lax about this (as evidenced by not even multiple programs agreeing). That's going to be a problem I suspect.

[orgopete]

The big utility of IUPAC names was a sort of "fingerprint" to classify molecules uniquely. i.e. Has this been made before?

This depends on the existance of a unique name for each molecule and a molecule for each name. Unfortunately IUPAC seems lax about this (as evidenced by not even multiple programs agreeing). That's going to be a problem I suspect.

Correct and correct.

If you have a nomenclature specialist, can you rely upon searching by name? It isn't IUPAC (or CAS) that is the problem, it is the structures themselves. IUPAC works perfectly well for simple compounds, but becomes unwieldily for larger or more complicated structures. Imagine how difficult it might be to read a chemistry paper if instead of some shorthand, e.g., a number, to refer to a structure, IUPAC names were used, ugh.

My company also had a nomenclature expert. That is how helped me with Chemical Abstracts nomenclature for patents. I don't believe the USPTO or the ACS restricts how things are named, per se. However, Chemical Abstracts picks up compounds from patents and papers and converts them into CAS nomenclature. If you are searching the CAS database, it is helpful to understand CAS names.

Let me repeat myself, IUPAC is a good system to teach systematic naming. If you know systematic naming, you will be in a better position to convert from any name, CAS, common, German, etc., into a structure. That is how I taught it. In class, I compared common with IUPAC so students could see how similar they were. Now, do you have some methanal, oh I mean formaldehyde?