Hi, I have a problem figuring out the name of these compounds (see attachment):

 

 

.mol files are attached in a .zip file.

 

Hope someone can help me with this,

 

 

sumi

mol files.zip

Hi, I have a problem figuring out the name of these compounds (see attachment):

 

Are you familiar with the [imath] [x.y.z...n] [/imath] IUPAC naming convention for multicyclics? Or do you have a copy of the ChemDraw software?

Edited February 17, 201114 yr by mississippichem

Are you familiar with the [imath] [x.y.z...n] [/imath] IUPAC naming convention for multicyclics?

 

Sadly no -.-

 

 

Or do you have a copy of the ChemDraw software?

 

I do but both ACD/ChemSketch and ChemAxon/MarvinSketch give me these apparently false names:

(1a) (1R,2S,7R,8S)-4,5-dichlorotricyclo[6.2.1.0^2,7]undeca-4,9-diene-1,8-dicarbonitrile

(1b) (1R,2R,7S,8S)-4,5-dichlorotricyclo[6.2.1.0^2,7]undeca-4,9-diene-1,8-dicarbonitrile

(2a) (1R,2S,7R,8S)-2,7-dichlorotricyclo[6.2.1.0^2,7]undeca-4,9-diene-1,8-dicarbonitrile

(2b) (1R,2R,7S,8S)-2,7-dichlorotricyclo[6.2.1.0^2,7]undeca-4,9-diene-1,8-dicarbonitrile

(3a) (1R,2S,7R,8S)-2-methoxy-3,6-dioxatricyclo[6.2.1.0^2,7]undec-9-ene-1,8-dicarbonitrile

(3a) (1R,2R,7S,8S)-2-methoxy-3,6-dioxatricyclo[6.2.1.0^2,7]undec-9-ene-1,8-dicarbonitrile

Edited February 17, 201114 yr by sumi

I tried putting the names together myself, now need someone to check them:

 

1a) (1R,4S,4aS,8aR)-4a,8a-dichloro-2,3,5,5,6,7,8,8-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

1b) (1R,4S,4aR,8aS)-4a,8a-dichloro-2,3,5,5,6,7,8,8-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

2a) (1R,4S,4aS,8aR)-6,7-dichloro-2,3,4a,5,5,8,8,8a-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

2b) (1R,4S,4aR,8aS)-6,7-dichloro-2,3,4a,5,5,8,8,8a-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

3a) (1R,4S,4aS,8aR)-4a-methoxy-5,8-dioxa-2,3,6,6,7,7,8a-heptahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

3b) (1R,4S,4aR,8aS)-4a-methoxy-5,8-dioxa-2,3,6,6,7,7,8a-heptahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

Hope someone can help me with this,

 

sumi

 

 

 

I tried putting the names together myself, now need someone to check them:

 

1a) (1R,4S,4aS,8aR)-4a,8a-dichloro-2,3,5,5,6,7,8,8-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

1b) (1R,4S,4aR,8aS)-4a,8a-dichloro-2,3,5,5,6,7,8,8-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

2a) (1R,4S,4aS,8aR)-6,7-dichloro-2,3,4a,5,5,8,8,8a-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

2b) (1R,4S,4aR,8aS)-6,7-dichloro-2,3,4a,5,5,8,8,8a-octahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

3a) (1R,4S,4aS,8aR)-4a-methoxy-5,8-dioxa-2,3,6,6,7,7,8a-heptahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

3b) (1R,4S,4aR,8aS)-4a-methoxy-5,8-dioxa-2,3,6,6,7,7,8a-heptahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

Hope someone can help me with this,

 

sumi

 

 

 

 

Not quite.

 

Check your ChemDraw structures are correct. I drew all of your compounds in ChemDraw and got different names to the ones you listed here and the ones you say ChemDraw spat back. Very close to the ones you listed above, but your naming of the 'hydro' bits is wrong. Everything else is okay in 1a and b. In 2a and 2b, two of your stereochemistry assignments are wrong. 3a and 3b are not correct either. As I say, double check your drawings in ChemDraw are exactly the same as the picture you inserted in your OP. You should get your names right that way.

 

 

 

To be honest, you shouldn't use ChemDraw to name your compounds. We have three versions of ChemDraw here and each one gave a different name for each of the compounds. And ChemDraw is far from perfect.

Check your ChemDraw structures are correct. I drew all of your compounds in ChemDraw and got different names to the ones you listed here and the ones you say ChemDraw spat back.

 

I don't have ChemDraw (does not work on my system), but ChemSketch (ACD)

 

 

 

Very close to the ones you listed above, but your naming of the 'hydro' bits is wrong. Everything else is okay in 1a and b. In 2a and 2b, two of your stereochemistry assignments are wrong. 3a and 3b are not correct either.

 

Possible Corrections:

 

1a) (1R,4S,4aS,8aR)-4a,8a-dichloro-1,4,4a,5,8,8a-hexahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

1b) (1R,4S,4aR,8aS)-4a,8a-dichloro-1,4,4a,5,8,8a-hexahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

2a) (1R,4S,4aR,8aS)-6,7-dichloro-1,4,5,6,7,8-hexahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

2b) (1R,4S,4aS,8aR)-6,7-dichloro-1,4,5,6,7,8-hexahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

3a) (4aS,5R,8S,8aR)-4a-methoxy-2,3,4a,5,8,8a-hexahydro-5,8-methanobenzo[1,4]dioxine-5,8-dicarbonitrile

3b) (4aR,5R,8S,8aS)-4a-methoxy-2,3,4a,5,8,8a-hexahydro-5,8-methanobenzo[1,4]dioxine-5,8-dicarbonitrile

Edited February 18, 201114 yr by sumi

Is the point of the exercise to learn to sue Chemdraw (or some such) or to learn how to name chemicals?

Is the point of the exercise to learn to sue Chemdraw (or some such) or to learn how to name chemicals?

Not my intention to sue anyone.

 

I was just pointing out why I was using other programs and that they apparently have trouble naming complex molecules correctly

 

=> thats why I asked for help here ...

 

 

 

Oops!

Is the point of the exercise to learn to use Chemdraw (or some such) or to learn how to name chemicals?

Oops!

Is the point of the exercise to learn to use Chemdraw (or some such) or to learn how to name chemicals?

sue vs use <-- nice one

 

 

anyway, tried again with a bit more reading and carefull thinking (only counting hydros that are actually new to basic structures of the naphthalene/bensodioxine rings) and came up with these (I dropped the Stereo, since that's already settled):

 

1a+b) 4a,8a-dichloro-5,8-dihydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

2a+b) 6,7-dichloro-4a,5,8,8a-tetrahydro-1,4-methanonaphthalene-1,4-dicarbonitrile

 

3a+b) 4a-methoxy-2,3,8a-trihydro-5,8-methanobenzo[1,4]dioxine-5,8-dicarbonitrile

 

puh ~ that was a long day(s) work. I'm gonna talk to my prof about these names tomorrow, and see what he thinks of them.

Edited February 20, 201114 yr by sumi

My prof tells me there a more than one way to name these compounds:

 

both the derviation from the bridged naphtalene/benzodixine ringsystem as well as from the tricyclic undecadiene ringsystem are possible.

 

Well, that settels that!