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Offline halcyonmind

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Nomenclature question II
« on: September 09, 2013, 08:54:44 AM »
Hi all, some nomenclature questions for those of you with a talent for and knowledge of such things:

I've made a series of compounds similar to A, in which the R groups form a polycyclic system. (See attached image.) I am naming them in two ways:

1) using a natural product as the parent hydride
2) using an IUPAC parent structure (morphinan) as the parent hydride

This gives the names:
1) 20-phenyl%naturalproduct%
2) (morphinan-7-yl)-(phenyl)methanone

Now I've made some ring-constrained analogues, including B and C, and I would like to name them using the same systems, but am struggling on how to do so. For B, I'm thinking something like:

1) [8, 20, 1', 2']-phenyl%naturalproduct%
2) morphinanyl[7, 8, 2, 3]2,3-dihydro-1H-inden-1-one

I'm not convinced either of these are correct:
For the first name I'm trying to show which carbons of the natural product connect to which atoms of the aryl ring.
For the second I'm trying to say that the morphinan and the 2,3-dihydro-1H-inden-1-one are fused so that atom 7 of the morphinan is atom 2 of the 2,3-dihydro-1H-inden-1-one and that atom 8 of the morphinan is atom 3 of the 2,3-dihydro-1H-inden-1-one. But I don't think what I've come up with can be correct I can't tell how to indicate that 2 and 3 refer to numbering of the 2,3-dihydro-1H-inden-1-one and 7 and 8 to numbering of the morphinan substituent.

Finally, the spiro compound, C. I've no experience with naming spiros so any pointers here would be massively appreciated.

Sorry, there are quite a few questions here. Please ask if I've not been sufficiently clear on anything.

Offline halcyonmind

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Re: Nomenclature question II
« Reply #1 on: September 09, 2013, 12:11:18 PM »
Ok so for the first naming system, for B, I think the answer is:

(8βH)-benzo[8,20]%naturalproduct%

Any thoughts?

3 more to go!
« Last Edit: September 09, 2013, 01:28:51 PM by halcyonmind »

Offline halcyonmind

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Re: Nomenclature question II
« Reply #2 on: September 09, 2013, 12:16:44 PM »
No, scrap that. That would mean that 8 and 20 were also part of the phenyl ring, which they're not. Back to square one :(
« Last Edit: September 09, 2013, 01:28:40 PM by halcyonmind »

Offline halcyonmind

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Re: Nomenclature question II
« Reply #3 on: September 09, 2013, 12:35:12 PM »
Ok, so the first naming system for B would maybe be this:

8,20-[1,2]benzeno-%naturalproduct%
« Last Edit: September 09, 2013, 01:28:29 PM by halcyonmind »

Offline halcyonmind

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Re: Nomenclature question II
« Reply #4 on: September 09, 2013, 12:47:34 PM »
An better attempt at naming B by the second naming system (using morphinan as a parent hydride):

(7S,8S)-(2,3-dihydro-1H-indenono)[2’,3’:7,8]morphinan

Do you think I can use "indeneno" like this?!
« Last Edit: September 09, 2013, 01:28:19 PM by halcyonmind »

Offline halcyonmind

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Re: Nomenclature question II
« Reply #5 on: September 09, 2013, 12:57:16 PM »
First naming system for C:

7,20-[α,2]tolueno-%naturalproduct%

or

7a,20-[1,2]tolueno-7a-homo%naturalproduct%

?!?!? I'm guessing here! And have absolutely no idea how to name this spiro compound using morphinan as the parent hydride (2nd naming system).
« Last Edit: September 09, 2013, 01:28:04 PM by halcyonmind »

Offline halcyonmind

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Re: Nomenclature question II
« Reply #6 on: September 09, 2013, 01:27:43 PM »
Ok, these are the answers I've come up with for B:

1) 8,20-[1,2]benzeno-%naturalproduct%
2) (7S,8S)-(2,3-dihydro-1H-indenono)[2’,3’:7,8]morphinan

and these for C:

1) 7,20-[α,2]tolueno-%naturalproduct% or 7a,20-[1,2]tolueno-7a-homo%naturalproduct%
2) Spiro[morphinan-7,2’-(2,3-dihydro-1H-inden-1-one)]

I'm not at all sure about these, so your feedback would be much appreciated.

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