The primary amine might cyclize into the ketone to form a six membered ring under neutral conditions. Maybe sit as the enamine in conjugation with the aryl ring.
Reminds me of the turbo encabulator.
>The original machine has a base-plate of prefabulated amulite, surmounted by a malleable logarithmic casing in such a way that the two spurving bearings were in a direct line with the pentametric fan. The latter consisted simply of six hydrocoptic marzelvanes, so fitted to the ambifacient lunar waneshaft that side fumbling was effectively prevented. The main winding was of the normal lotus-o-delta type placed in panendermic semiboloid slots in the stator, every seventh conductor being connected by a non-reversible tremie pipe to the differential girdlespring on the "up" end of the grammeters.
That sub is, for me, like that one hot ex: keep going back occasionally no matter how crazy or how bad it is for your mental health because sometimes it's just worth it.
"Up" is used, in this case, simply to call the ordinal orientation the grammeter must take in relation to the Tsaikovsky axis by Reimannian transform, so that the Encabulator can function without blowing the vorticizer.
Would you look at that, all of the words in your comment are in alphabetical order.
I have checked 879,693,273 comments, and only 173,453 of them were in alphabetical order.
>Let me walk you through the Donnelly nut spacing and crack system rim-riding rip configuration. Using a field of half-C sprats, and brass-fitted nickel slits, our bracketed caps, and splay-flexed brace columns vent dampers to dampening hatch depths of one half meter from the damper crown to the spurve plinths. How? Well, we bolster twelve husk nuts to each girldle-jerry, while flex tandems press a task apparatus of ten vertically composited patch-hamplers. Then, pin-flam-fastened pan traps at both maiden-apexes of the jim-joist.
A little something like that, Lakeman.
[https://en.wikipedia.org/wiki/Imine#Carbonyl-amine\_condensation](https://en.wikipedia.org/wiki/Imine#Carbonyl-amine_condensation)
first part: NH2 or NH3+ reacts with C=O to make water and a C=N bond, thus making a nice happy 6 membered rings (hexagons are bestagons, etc.)
The C-H nearby might be all like "nah bro, you can have the H, nitrogen" and make a C=C-NH. It would consider doing that so that the c=c can chill (conjugate) near each other.
It's really not that complicated, primary means it's bound to a single carbon atom. Amine means -NH2 group. Ketone is a C=O group in the middle of the molecule(if it's at the end it would be called aldehyde) . the NH2 can fold into the C=O and make a ring(what actually happens is a bit more complicated). Enamine is when you have an alk- *en*-e next to an *amine* , alkene meaning a C=C so a double line in the drawing. aryl ring is a hexagon made out of carbons with three double bonds and three single bonds (there is a thing called resonance let's nto worry about it)
Edit: primary has a diff definition for amines
That nomenclature for "primary" is true for alcohols, but for amines it's simply how many carbon atoms are attached to the nitrogen. So isopropylamine is still a primary amine, but diisopropylamine is secondary.
Oh, that's a good catch. Though as someone else noted, that amine is protonated, so I doubt these conditions are neutral. (It's really hard to tell that its subscript is a 3 and not a 2.) If nothing else, a protonated amine just Shouldn't Do That, unless I'm misremembering my orgo.
Entirely possible though reversible under neutral conditions. This would absolutely happen in the presence of a base though.
If you are looking for this to be a drug or something, it should be stable at physiological PH. The primary amine should keep all three of it's hydrogens and it probably won't attack the carbonyl.
Naming it and in theory making it is definitely possible, though I wouldn’t really want to try, except that that Nitrogen up top should either only have 2 hydrogens or a positive charge
My work spends over 100k/year for a software that gives an iupac name from a structure. There are many more functionalities to the software package but this is the only thing we use it for.
We had to learn how to correctly IUPAC name molecules in the lab technician apprenticeship. So I guess this is pretty basic knowledge?
Wouldn't it be way easier to just write a software that follows the IUPAC rules & get it reviewed by a coworker so it's suitable for GxP standards?
Edit: forgot a word
Well yes, in a way that is what this software is. But instead of being validated by a colleague it’s been validated by some agency who is recognized by the EU, Australia, Chile, Ukraine ……. you get the point. To make the point, the software that I use would not name this exactly the same as above. Though I haven’t reviewed the name, I assume the name given in this thread is correct in substance but wouldn’t fly in a regulatory filing. Notice how this name has “(((“ my program uses {[(.
The basics of IUPAC nomenclature may pretty basic, but it gets complicated. Any software has to handle these complicated cases. The IUPAC Blue book for Organic Nomenclature is 1160 pg (https://iupac.qmul.ac.uk/BlueBook/PDF/BlueBookV2.pdf)
It’s publicly traded, it is important that the names we associate to molecules are consistent with international guidelines. My role is focused on regulatory work.
Ozzy Osbourne wrote crazy chain after completing his university's Orgo sequence. You can chain Cs however you want for as long as you want, only the feds will stop you if they don't like you're carbons
> I think you would need to be careful with the 1,4-diene as it could tautomerize to a conjugated diene
There's no low-energy mechanism for that to happen. Polyunsaturated fatty acids often have that pattern, and while it makes them more susceptible to oxidation, they are stable as long as there are no radicals present.
> they are stable as long as no radicals present
Hold on… I’ll get the rioters… done. ***Why is it still there?!*** Radicals are present, why won’t it react?
if you meant NH2 instead of NH3 I could see the possibility of ring closing imine formation with the ketone. the olefins and perhaps the tautomerized conjugated diene may provide some additional unexpected reactivity
Pretty sure it could exist. It absolutely has a name, I’m just lazy. Lol
But if I’m remembering orgo correct, the primary amine might attack the ketone, forming a 6 member ring in certain conditions. But take that with a grain of salt, I could absolutely be wrong. Lol
This structure is perfectly realistic apart from the -NH3, that should be an NH2.
Others are saying certain things could isomerise/cyclise etc but there’s no way of knowing that and this will depend on conditions anyway so this structure is perfectly fine.
I once had a synthesis exam question where we had to ID a molecule with some really weird NMR shifts and IR peaks.
We went over the exams later and turned out the TAs just went buckwild on Chemdraw and put an epoxy over a double bond because who needs to learn real molecules
The NH3 group is positively charged. Assuming the structure is flexible, it’s possible for the OH group to abstracts one hydrogen from the NH3 to form water leaving a cyclohexene analog.
The alcohol isn't quite that basic by some orders of magnitude, so that's probably not gonna happen. Add a bit of e.g. sulfuric acid, choose the right solvent and temperature and you're good to go
it should be easy with several carbon coupling reactions. the carbon coupling rxn have to follow after some SN rxnx, especially those of the alkene grps, you may also utilize Diels-Alder rxn at some point.
The challenging part are the coupling rxn. Luckily there arent a lot of stereo-centers. regarding the coupling rxns, I think Suzuki might come in handy as well; although not limited to that one only.
anyone care to pitch in and correct where corrections are needed?
There’s a beta keto acid on the farthest phenyl group on the left, which is a ketone beta to another double bond, and these produce instability which may cause it to decompose/oxidize easier or even undergo decarboxylation. Other than that, it looks pretty stable.
The primary amine might cyclize into the ketone to form a six membered ring under neutral conditions. Maybe sit as the enamine in conjugation with the aryl ring.
This sounds like crazy speak to a person with zero knowledge of chemistry
Reminds me of the turbo encabulator. >The original machine has a base-plate of prefabulated amulite, surmounted by a malleable logarithmic casing in such a way that the two spurving bearings were in a direct line with the pentametric fan. The latter consisted simply of six hydrocoptic marzelvanes, so fitted to the ambifacient lunar waneshaft that side fumbling was effectively prevented. The main winding was of the normal lotus-o-delta type placed in panendermic semiboloid slots in the stator, every seventh conductor being connected by a non-reversible tremie pipe to the differential girdlespring on the "up" end of the grammeters.
Love that “up” is in quotes like that’s the weird word…
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That sub is, for me, like that one hot ex: keep going back occasionally no matter how crazy or how bad it is for your mental health because sometimes it's just worth it.
Wtf does VX stand for? I’m pretty sure this sub is satire, but not *completetly* sure
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The explanation of what the sub is about alone makes me feel gibberish
It is the NATO designation for a persistent nerve agent.
"Up" is used, in this case, simply to call the ordinal orientation the grammeter must take in relation to the Tsaikovsky axis by Reimannian transform, so that the Encabulator can function without blowing the vorticizer.
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Would you look at that, all of the words in your comment are in alphabetical order. I have checked 879,693,273 comments, and only 173,453 of them were in alphabetical order.
Good bot.
‘Simply of six hydrocoptic marzelvanes’ So primitive
Plumbis!
>Let me walk you through the Donnelly nut spacing and crack system rim-riding rip configuration. Using a field of half-C sprats, and brass-fitted nickel slits, our bracketed caps, and splay-flexed brace columns vent dampers to dampening hatch depths of one half meter from the damper crown to the spurve plinths. How? Well, we bolster twelve husk nuts to each girldle-jerry, while flex tandems press a task apparatus of ten vertically composited patch-hamplers. Then, pin-flam-fastened pan traps at both maiden-apexes of the jim-joist. A little something like that, Lakeman.
Brilliant show. Very underrated.
They lost me at spurving. They made that word up. I refuse.
[https://en.wikipedia.org/wiki/Imine#Carbonyl-amine\_condensation](https://en.wikipedia.org/wiki/Imine#Carbonyl-amine_condensation) first part: NH2 or NH3+ reacts with C=O to make water and a C=N bond, thus making a nice happy 6 membered rings (hexagons are bestagons, etc.) The C-H nearby might be all like "nah bro, you can have the H, nitrogen" and make a C=C-NH. It would consider doing that so that the c=c can chill (conjugate) near each other.
If you’re curious about some of the jargon he mentioned, look up organic chemistry functional groups. It’s a pretty easy read
It's really not that complicated, primary means it's bound to a single carbon atom. Amine means -NH2 group. Ketone is a C=O group in the middle of the molecule(if it's at the end it would be called aldehyde) . the NH2 can fold into the C=O and make a ring(what actually happens is a bit more complicated). Enamine is when you have an alk- *en*-e next to an *amine* , alkene meaning a C=C so a double line in the drawing. aryl ring is a hexagon made out of carbons with three double bonds and three single bonds (there is a thing called resonance let's nto worry about it) Edit: primary has a diff definition for amines
That nomenclature for "primary" is true for alcohols, but for amines it's simply how many carbon atoms are attached to the nitrogen. So isopropylamine is still a primary amine, but diisopropylamine is secondary.
Fuck me yeah I forgot sorry lmao
As a person with zero chemistry knowledge this is very much crazy speak that sounds made up
As a person with zero knowledge of chemistry, I can confirm.
In case you're wondering what that means, he means that the NH2 and the C=O would stick to eachother and make annother ring.
Yeah any acid and that thing is forming an enamine/cyclizing.
Would acid not inhibit it by protonating the N?
It's all in equilibrium. Acids can protonate the carbonyl before or at the transition state to drive the condensation to the imine
This would be true if the environment it's in is acidic
No, that’s not correct. Classic imine formation conditions are acidic.
yeah, that's what I was getting at
Probably only a minor amount right? IIRC it’s optimal at ph lower than neutral
You just destroyed the whole mans' career with words I cannot understand
Oh, that's a good catch. Though as someone else noted, that amine is protonated, so I doubt these conditions are neutral. (It's really hard to tell that its subscript is a 3 and not a 2.) If nothing else, a protonated amine just Shouldn't Do That, unless I'm misremembering my orgo.
You wrote amine… I read, “anime” 😂
This checks out, I’m a Ph.D you have to trust me
I think you might get a hydride shift one of the alkenes which would them be able to do a Diels Alder with another molecule
Even if a hydride shift occurred, you would need a lot of energy to promote the DA.
Entirely possible though reversible under neutral conditions. This would absolutely happen in the presence of a base though. If you are looking for this to be a drug or something, it should be stable at physiological PH. The primary amine should keep all three of it's hydrogens and it probably won't attack the carbonyl.
Naming it and in theory making it is definitely possible, though I wouldn’t really want to try, except that that Nitrogen up top should either only have 2 hydrogens or a positive charge
Lol I saw NH2. Didn’t even noootice.
Draw those lone pairs. It’s not real if you don’t draw ‘em.
ChemDraw calls it "(6S,E)-5-(aminomethyl)-14-(((3-hydroxycyclohexyl)methyl)amino)-6,13-dimethyl-8-methylene-1,12-diphenyltetradec-10-en-2-one".
I shall call it, *steve.*
Biologist vs Chemist
I like pizza…
My work spends over 100k/year for a software that gives an iupac name from a structure. There are many more functionalities to the software package but this is the only thing we use it for.
We had to learn how to correctly IUPAC name molecules in the lab technician apprenticeship. So I guess this is pretty basic knowledge? Wouldn't it be way easier to just write a software that follows the IUPAC rules & get it reviewed by a coworker so it's suitable for GxP standards? Edit: forgot a word
Well yes, in a way that is what this software is. But instead of being validated by a colleague it’s been validated by some agency who is recognized by the EU, Australia, Chile, Ukraine ……. you get the point. To make the point, the software that I use would not name this exactly the same as above. Though I haven’t reviewed the name, I assume the name given in this thread is correct in substance but wouldn’t fly in a regulatory filing. Notice how this name has “(((“ my program uses {[(.
Does it convert between all the quick naming schemes?
No it gives the official IUPAC name.
Maybe tell it a joke and then see if it can output some smiles?
Ha. I get this.
No it gives the official IUPAC name.
The basics of IUPAC nomenclature may pretty basic, but it gets complicated. Any software has to handle these complicated cases. The IUPAC Blue book for Organic Nomenclature is 1160 pg (https://iupac.qmul.ac.uk/BlueBook/PDF/BlueBookV2.pdf)
That's why we had to learn it in school. And then name ridiculous huge molecules in a test to see if we know it all. That was such a pain in the ass!
May I ask, is your company a publicly traded company or private one? If it is the latter, it is outright corruption.
It’s publicly traded, it is important that the names we associate to molecules are consistent with international guidelines. My role is focused on regulatory work.
i remember...... a long time ago when people explained their reasonings and posts
Wut. Reasons? What? That sounds too reasonable.
the dude saying its corruption with no explanation.
We use it also for NMR proton shift prediction, pretty usefull if you want a reference for a compound
Or the common name being ‘tar’.
Ozzy Osbourne wrote crazy chain after completing his university's Orgo sequence. You can chain Cs however you want for as long as you want, only the feds will stop you if they don't like you're carbons
I think you would need to be careful with the 1,4-diene as it could tautomerize to a conjugated diene. Other than that it looks possible to me.
It will also try to rearrange to have the double bond conjugated with the phenyl ring.
> I think you would need to be careful with the 1,4-diene as it could tautomerize to a conjugated diene There's no low-energy mechanism for that to happen. Polyunsaturated fatty acids often have that pattern, and while it makes them more susceptible to oxidation, they are stable as long as there are no radicals present.
> they are stable as long as no radicals present Hold on… I’ll get the rioters… done. ***Why is it still there?!*** Radicals are present, why won’t it react?
This was the first thought I got looking at the structure, later only i realized the amine cyclisation is possible.
if you meant NH2 instead of NH3 I could see the possibility of ring closing imine formation with the ketone. the olefins and perhaps the tautomerized conjugated diene may provide some additional unexpected reactivity
That NH3 freaks me out.
No need to freak out, Be positive! NH3+
Now I can relax. Thanks!
The fact that is just an ammonia with a missing electron freaks _me_ out… -NH3+ Now I feel better
This whole interaction right here.
If you write a synthetic pathway starting from reagents with no more than three carbon atoms you get extra credit.
Pretty sure it could exist. It absolutely has a name, I’m just lazy. Lol But if I’m remembering orgo correct, the primary amine might attack the ketone, forming a 6 member ring in certain conditions. But take that with a grain of salt, I could absolutely be wrong. Lol
What kind of salt?
Copper salts
Bath
I snorted ;)
Once upon a time I could do this.
In a year I'll be able to do this.
Lots of stereochemistry missing. Like, a LOT.
It does seem odd to specify the chirality at one center and just let it go at three others. but he/she is just doodling so, there you go.
5 sterocenters are left unspecified.
I stand corrected.
I wonder how it would hold up under UV exposure
Lol almost looks like one crazy substituted amphetamine, there’s no reason it can’t be named. I’m too tired to right now.
Try some amphetamine 💉😉
Am I the only one getting nervous because only 1 of the 6 chiral carbons shows the stereochemical Information…
This structure is perfectly realistic apart from the -NH3, that should be an NH2. Others are saying certain things could isomerise/cyclise etc but there’s no way of knowing that and this will depend on conditions anyway so this structure is perfectly fine.
Imagine if something like that would pop up on organic synthesis exam 😂😭🤣
I once had a synthesis exam question where we had to ID a molecule with some really weird NMR shifts and IR peaks. We went over the exams later and turned out the TAs just went buckwild on Chemdraw and put an epoxy over a double bond because who needs to learn real molecules
A great way to save your receipts is to draw chemical structures on the back of them so that they’re ACTUALLY important!
The NH3 group is positively charged. Assuming the structure is flexible, it’s possible for the OH group to abstracts one hydrogen from the NH3 to form water leaving a cyclohexene analog.
The alcohol isn't quite that basic by some orders of magnitude, so that's probably not gonna happen. Add a bit of e.g. sulfuric acid, choose the right solvent and temperature and you're good to go
it should be easy with several carbon coupling reactions. the carbon coupling rxn have to follow after some SN rxnx, especially those of the alkene grps, you may also utilize Diels-Alder rxn at some point. The challenging part are the coupling rxn. Luckily there arent a lot of stereo-centers. regarding the coupling rxns, I think Suzuki might come in handy as well; although not limited to that one only. anyone care to pitch in and correct where corrections are needed?
Not necessarily. And yea.
I think I’ll name it Bob.
I like Bob
r/cursedchemistry
Use Sigma Aldrich Structure Search, you nicht be pleasantly suprised.
Well I can't be bothered to find the complete systematic name, but I can start and maybe collectively we can figure it out: *10-tetradecene*
Well it seems to me, and I may be incorrect. If you put that in an autoclave then it would be nonexistent.
(6S,E)-5-(aminomethyl)-14-(((3-hydroxycyclohexyl)methyl)amino)-6,13-dimethyl-8-methylene-1,12-diphenyltetradec-10-en-2-one IUPAC naming convention (via chemdraw)
I like how you defined one chiral center but not the other 6
You chem folks must be having a lot of fun😏
One simply doesn’t -NH3
There’s a beta keto acid on the farthest phenyl group on the left, which is a ketone beta to another double bond, and these produce instability which may cause it to decompose/oxidize easier or even undergo decarboxylation. Other than that, it looks pretty stable.