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Record W1916198087 · doi:10.1002/ejoc.201403142

Synthesis of Saturated Benzodioxepinone Analogues: Insight into the Importance of the Aromatic Ring Binding Motif for Marine Odorants

2014· article· en· W1916198087 on OpenAlexafffund
Christopher M. Plummer, Robert Gericke, Philip Kraft, Aaron M. Raynor, Jordan Froese, Tomáš Hudlický, Trevor J. Rook, Oliver A.H. Jones, Helmut Hügel

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2014
Typearticle
Languageen
FieldNeuroscience
TopicOlfactory and Sensory Function Studies
Canadian institutionsBrock University
FundersRMIT UniversityMcMaster University
KeywordsChemistryMoietyStereochemistrySubstituentRing (chemistry)AromaticityMolecular modelAlkeneMoleculeOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract As part of our research exploring the influence of molecular variations of Calone 1951 ® on marine fragrance performance, we report the synthesis, crystal structures, and olfactory analysis of the first saturated benzodioxepinone analogues. By substitution of the aromatic moiety of the benzodioxepinone fragrance molecule with a saturated ring counterpart, we endeavoured to discover the molecular interactions of the aromatic and aliphatic rings with fragrance receptor sites, and also to shed light on any potential chiral interactions occurring within the receptor. Our results showed that an aromatic ring system is necessary for binding to the marine odour receptor(s), and that the addition of an alkene or methyl substituent has little effect on the low receptor affinity. However, a weak marine odour character was found for the 6‐methyl saturated derivatives, which could possibly be explained by superposition analysis of the respective structures, which were derived from X‐ray coordinates.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.004
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.009
Threshold uncertainty score0.501

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.004
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.049
GPT teacher head0.226
Teacher spread0.177 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations8
Published2014
Admission routes2
Has abstractyes

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