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/sci/ - Science & Math

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7349702 No.7349702 [Reply] [Original]

Calling all Chemists and Scholars!
I come in need of an IUPAC name for this chemical!

It comes from organic chemistry I lab from the double aldol condenstation of 4-methoxybenzaldehyde with cyclopentanone.

This goes outside the scope of my ability to determine a proper name, so I ask for help from /sci/. Along with an IUPAC name, does this chemical go by any common name? It is a flakey, bright yellow dye.

>> No.7349711

>>7349702
Sulfur

>> No.7349772

>>7349702
Are you active right now OP?

>> No.7349780

>>7349772
I got this...
Z,Z-1,5-Di-(1,4-vinylmethoxybenzene)cyclopent-1,5-di-en-1-one. Ketone takes the highest priory eh so everything else is a substituent of the cyclopentanone right? Its not right, I honestly don;t know how to name it but this is as close as I can get it.

>> No.7349784

>>7349702
2,5-bis((E)-4-methoxybenzylidene)cyclopentan-1-one

just use chemdraw next time

>> No.7350128
File: 7 KB, 599x193, sclareol.png [View same] [iqdb] [saucenao] [google]
7350128

Fellow synthetic chemists...

How would you semi-synthesize sclareol (left) from sclareolide (right)?

My initial idea was reduce the lactone to a diol then selectively oxidize the primary alcohol to an aldehyde
OR directly reduce the lactone to sec-alcohol + aldehyde (how?)
OR hydrolyze the lactone then reduce the carboxylate moiety...
Then react the carbonyl with a Wittig reagent, and regioselectively add water on the diene to get the alcohol.

Any thoughts?

>This is not homework, btw.

>> No.7350130

>>7350128
>sec-alcohol
*tertiary alcohol

>> No.7350230

Why that molecule is fairly clearly 2-poopanone. You must have missed the lecture on benzoic depoopification reactions.

>> No.7351018

>>7350128
You can also do a rearrangement

>> No.7351187
File: 76 KB, 750x479, 1434227977913.jpg [View same] [iqdb] [saucenao] [google]
7351187

>>7350128
>reduce the lactone to a diol then selectively oxidize the primary alcohol to an aldehyde

Do you mean hydrate the alkene and then selectively oxidize it, then esterify the aldehyde?

How would you get rid of the hydroxyl and methyl groups that would be sitting on the α position from the ester?

>> No.7352045
File: 7 KB, 599x193, sclareol_fixed.png [View same] [iqdb] [saucenao] [google]
7352045

>>7351018 >>7351187

My apologies, I got confused. I want to synthesize sclareol (right) from sclareolide (the lactone, on the left).

I had to redraw both structures to make the common carbon skeleton obvious, and swapped their names along the way.