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View Code? Open in Web Editor NEWThis repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
Link to HIRAC, original method and [master page].
KBS22 Linear amine click coupling with azidoadamantane.docx
256 mg (0.343 mmol), 109%
Link to HIRAC and original method.
HIRAC Deprotection of bis-adamantane cyclam .docx
Previous attempt was in Honours.
339 mg (0.482 mmol), 86%
Link to HIRAC and master page.
KBS26 Deprotection of bis-adamantyl 1,6-diaminohexane.docx
90 mg of HCl salt obtained - this exceeds 100% yield
Link to HIRAC and master page. Method developed from Julius Adamson.
Ferrocenyl methyl ester synthesis .docx
715 mg (2.93 mmol), 67%
Further extractions would likely improve yield, but are time consuming. Consider alternative method here for next time.
Link to HIRAC, original method and master page.
1.362 g (6.07 mmol), 62.2%
Make sure to chill reaction and do not leave much longer than 1 hr.
Link to HIRAC, original method and master page.
Last attempt is #28
Next attempt is #33
KBS17 Generic propargylation of 1,n-diamine.docx
Using 1:5 mixture of DMF:THF as solvent.
Link to HIRAC, original method and master page.
KBS16 Ferrocenylmethanol to azidomethylferrocene DPPA.docx
Next attempt is #27.
236 mg (0.978 mmol), 64%
Link to HIRAC, original method and master page.
Next attempt is #22.
KBS17 Generic propargylation of 1,n-diamine.docx
Molecular weights
SM = 316.44
Product = 392.54
Predicted side product (mono-propargylated) = 354.49
Only side product recovered (175 mg, 38%).
Link to HIRAC, original method and master page.
KBS9 Bis-propargylation of bridged cyclam.docx
1.9539 g (3.23 mmol), 72%
Link to HIRAC, original method and master page.
KBS25 Propargylation of unprotected 1,6-diaminohexane.docx
Attempting to alkylate unprotected amine
Looks good, minor solvent impurities between 1-3 ppm.
Link to HIRAC and master page.
Next attempt is #18
Ferrocenylmethanol synthesis .docx
332 mg (1.54 mmol), 95%
Ready to carry through to azidation.
Link to HIRAC, original method and master page.
Last attempts are #19 and #23.
KBS17 Generic propargylation of 1,n-diamine.docx
Link to HIRAC, original method and master page.
Last attempt is #22.
KBS17 Generic propargylation of 1,n-diamine.docx
20 mg (0.0510 mmol), 10%
Overall, it does not seem to be worth attempting to "re-react" the mono product to obtain more of the bis product, as the yield was so poor. In future, the reaction will simply be uspcaled, though optimisation of solvents etc will still be attempted.
Link to HIRAC, original method and master page.
HIRAC doc file: KBS11 Azidation of 1-adamantane.docx
Reaction Scheme
Outcome
N/A - solids recovered appeared to be starting material rather than desired product
Altering solvent from THF to DMF (after repeated failure with THF). Remember to wash out DMF (5 x wash with water).
Link to HIRAC, original method and master page.
KBS11 Azidation of 1-adamantane.docx
54 mg (0.305 mmol), 7%
Not fully purified. Not pursued due to human error (spillage) resulting in low yield.
Link to HIRAC and original method.
KBS16 Ferrocenylmethanol to azidomethylferrocene DPPA.docx
Reaction Scheme
Outcome
49 mg (0.204 mmol), 45%
TLC indicated reaction completion - is low yield due to loss during purification?
Link to HIRAC and master page.
Ferrocenylmethanol synthesis .docx
356.7 mg (1.65 mmol), 98%
Link to HIRAC, original method and [master page.
KBS19 Deprotection of bis-methylferrocene cyclam.docx
137 mg - impure
Link to HIRAC, original method and master page.
HIRAC doc file: KBS11 Azidation of 1-adamantane.docx
Reaction Scheme
Outcome
N/A - crude product appeared to be desired compound, but was lost in purification
Need to optimise purification techniques.
Link to HIRAC and master page. Method adapted from Shieh et al., 2002.
KBS14 ALTERNATIVE (DBU method) .docx
155.4 mg (0.637 mmol), 70% (still slightly wet)
Link to HIRAC, and master page. Original method from J. Batten's PhD thesis, but a similar method is used by Babin et al..
KBS22 Azidation of 1-naphthylamine.docx
191.6 mg (1.13 mmol), 66%
Sufficiently pure to carry through to next step.
Link to HIRAC and master page.
KBS17 Generic propargylation of 1,n-diamine.docx
Crude: 355 mg (0.844 mmol), 70%
Link to HIRAC, original method and master page.
Last attempt is #45.
KBS17 Generic propargylation of 1,n-diamine.docx
Link to HIRAC, original method and master page.
Last attempt is #32. Next attempt is #45.
KBS17 Generic propargylation of 1,n-diamine.docx
Using DMF as solvent. Add NaH portionwise (and use only 3 equiv.), allow 1-2 hrs reaction time and cool reaction to 0 C before adding propargyl bromide.
Link to HIRAC and master page. Method adapted from Shieh et al., 2002.
KBS14 ALTERNATIVE (DBU method) .docx
Mass of 123.3 mg (unpurified, containing more SM than product). May be due to not allowing reaction to go to completion - next time, will add 1.2 equiv. of DBU at beginning and possibly allow longer reaction times.
Link to HIRAC, original method and master page.
KBS16 Ferrocenylmethanol to azidomethylferrocene DPPA.docx
110 mg, 40%
TLC indicated reaction completion - is low yield due to loss during purification?
Link to HIRAC, original method and master page.
Last attempt is #33.
KBS17 Generic propargylation of 1,n-diamine.docx
Link to HIRAC, original method and master page.
KBS16 Ferrocenylmethanol to azidomethylferrocene DPPA.docx
Previous attempt was #17.
Link to HIRAC and master page.
Last attempt was #15.
Ferrocenylmethanol synthesis .docx
354 mg (1.64 mmol), 104% - traces of ethyl acetate but ready to carry through.
N/A
Link to HIRAC and master page.
KBS3 Generic boc protection of 1,n-diamine.docx
1.241 g (3.60 mmol), 100%
Link to HIRAC, original method and [master page].
KBS24 Linear amine click coupling with azidomethylferrocene.docx
62.1 mg (0.071 mmol), 70%
Link to HIRAC and master page. Method developed from Julius Adamson.
Ferrocenyl methyl ester synthesis .docx
333.4 mg (1.37 mmol), 34% (impure)
After columning: 166.1 mg (0.681 mmol), 17%
Poor outcome - likely had product remaining in aqueous layer.
Small amount of product volatilises and ended up in solvent trap after rotovapping to remove methanol (confirmed to be product by TLC and NMR).
("?" = red colour crystals from solvent trap, "Fc" = ferrocenecarboxylic acid SM, "14" = sample of KBS14 ferrocenyl methyl ester)
Link to HIRAC, original method and master page.
KBS10 Bridge hydrolysis + boc protection of bis-propargyl cyclam.docx
1.805 g (3.79 mmol), 128%
N/A
Link to past attempts #10 or master pages with overviews of your work
Link to external webpages like relevant papers - e.g. Spain et al., 2018
Include experimental data and safety documents - e.g. KBS16-4 Proton NMR.zip
Edit posts from your mobile device!
Link to HIRAC, original method and master page.
KBS11 Azidation of 1-adamantane.docx
N/A
No evidence of product in NMR. Abandoned.
Link to HIRAC, original method and master page.
Last attempt is #19.
Next attempt is #23
KBS17 Generic propargylation of 1,n-diamine.docx
Using 1:5 mixture of DMF:THF as solvent.
62% overall
Mono product: 164 mg (0.462 mmol), 36%
Bis product: 129 mg (0.330 mmol), 26%
Link to HIRAC, original method and master page.
Last attempt is #45.
KBS17 Generic propargylation of 1,n-diamine.docx
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