58471-10-6

Usage

Uses

Unfortunately, the provided materials do not mention any specific applications or uses for darlingine. However, as a tropane type alkaloid, it may have potential applications in various industries, such as pharmaceuticals, agriculture, or chemical research. Further research and development would be required to explore and confirm its potential uses.

References

Bick, Gillard, Woodruff, Chern. Ind. (London), 794 (1975)

InChI:InChI=1/C13H17NO2/c1-7-8(2)16-11-6-9-4-5-10(14(9)3)12(11)13(7)15/h9-10H,4-6H2,1-3H3

Upstream product

• 532-24-1 tropinone 
• 115494-38-7 tigloyl cyanide 
• 72362-48-2 (5S)-2ξ,3ξ,10-trimethyl-2,3,6,7,8,9-hexahydro-5H-5r,8c-epiazano-cyclohepta[b]pyran-4-one 

Relevant academic research and scientific papers

Tropane alkaloids from Darlingia darlingiana

A new γ-pyranotropane, darlingine N-oxide, was isolated from the bark and leaves of Darlingia darlingiana, along with the known compound, darlingine. 1D-NOESY NMR experiments indicated that the N-methyl groups of both alkaloids were orientated towards the pyran ring.

Synthesis of tropane alkaloids via enantioselective deprotonation of tropinone

Enantioselective deprotonation of tropinone 2 with chiral lithium amides 5a and 6a, in the presence of LiCl, gave tropinone lithium enolate in up to 95% ee. The C2 symmetrical lithium amide 6a worked best when it was generated in situ from the hydrochloride salt of the corresponding amine 6b. The deprotonation was used as the key step in synthesis of tropane alkaloids:ent-anhydroecgonine, ent-knightinol, KD-B, chalcostrobamine, ent-isobellendine, and ent-darlingine. The absolute configuration of natural benzyltropane and pyranotropane alkaloids was established (by correlation with anhydroecgonine) to be 'cocaine-like' i.e., the side chain originates at C-2 of the tropane ring system in all cases.