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Record W2132739352 · doi:10.1002/047084289x.rb346

α,β-Butenolide

2001· reference-entry· en· W2132739352 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicOrganic Chemistry Synthesis Methods
Canadian institutionsUniversité Laval
Fundersnot available
KeywordsRegioselectivityChemistryVicinalStereoselectivityTolueneSolubilityOrganic chemistryMedicinal chemistryCatalysis

Abstract

fetched live from OpenAlex

[497-23-4] C4H4O2 (MW 84.07) InChI = 1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 InChIKey = VIHAEDVKXSOUAT-UHFFFAOYSA-N (can be transformed into derivatives of 2-furanol including esters2 and silyl ethers;3 provides 3-(1′-hydroxyalkyl)-2(5H)-furanones by regioselective aldolization;4 undergoes highly regio- and stereoselective reactions with sulfinylallyl anions;5 serves as keystone for the convergent assembly of lignans6 and prostaglandin analogs7 through tandem vicinal difunctionalization8) Alternate Names: γ-crotonolactone; 2(5H)-furanone; but-2-en-4-olide. Physical Data: bp 86–87 °C/12 mmHg; mp 5 °C; d 1.185 g cm−3. A pKa value of 18.8 has been determined for its equilibrium acidity in DMSO (pKHA), but this may not be correct.9 Solubility: sol most organic solvents, e.g. CCl4, CH2Cl2, Et2O, toluene, THF, MeOH, and MeCN. Form Supplied in: colorless or pale yellow liquid, commercially available; expensive. Preparative Methods: obtainable by oxidation of furfural10 or by dehydrobromination of α-bromo-γ-butyrolactone10a,11 at very low cost. Handling, Storage, and Precautions: avoid contact with skin or eyes; do not inhale or ingest; vapor is irritating to the eyes and upper respiratory track. It should be stored at 4 °C or below. Use in a fume hood.

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.

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)0.009
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMetaresearch, Meta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.512
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.009
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0650.000

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 head0.023
GPT teacher head0.275
Teacher spread0.252 · 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