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Record W2127518968 · doi:10.1002/047084289x.rd316

Dimethyl 3-Bromo-2-ethoxy-1-propenylphosphonate

2001· reference-entry· en· W2127518968 on OpenAlexaff
Edward Piers, Christine Rogers

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicOrganophosphorus compounds synthesis
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsReagentPhosphonateChemistryTriethyl orthoformateNuclear chemistrySolubilityOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

(E) [73542-48-0] C7H14BrO4P (MW 273.08) InChI = 1S/C7H14BrO4P/c1-4-12-7(5-8)6-13(9,10-2)11-3/h6H,4-5H2,1-3H3 InChIKey = BDAMDKOGBQRUDC-UHFFFAOYSA-N (Z) [87278-14-6] InChI = 1S/C7H14BrO4P/c1-4-12-7(5-8)6-13(9,10-2)11-3/h6H,4-5H2,1-3H3/b7-6+ InChIKey = BDAMDKOGBQRUDC-VOTSOKGWSA-N [119226-85-6] InChI = 1S/C7H14BrO4P/c1-4-12-7(5-8)6-13(9,10-2)11-3/h6H,4-5H2,1-3H3/b7-6- InChIKey = BDAMDKOGBQRUDC-SREVYHEPSA-N (reagent for effecting cyclopentenone annulations2, 3) Physical Data: colorless liquid; distillation temperature (bulb-to-bulb) 110 °C/0.05 mmHg. Solubility: sol THF, CHCl3, EtOAc, and other common organic solvents. Preparative Methods: is readily prepared in two steps from the commerically available keto phosphonate 1.2b Reaction of 1 with Triethyl Orthoformate in the presence of FeCl3·6H2O, followed by allylic bromination of the resultant enol ether 2, provides the title reagent 3 in 71% overall yield (eq 1). (1) Handling, Storage, and Precautions: should be used shortly after its preparation and should be handled only in a well-ventilated 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.

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)0.005
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.530
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.005
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0030.001
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0030.001
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0620.001

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 head0.017
GPT teacher head0.243
Teacher spread0.226 · 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; both teacher heads agree on what is shown here.

Study designNot applicable
Domainnot available
GenreOther

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

Citations0
Published2001
Admission routes1
Has abstractyes

Explore more

Same venueEncyclopedia of Reagents for Organic SynthesisSame topicOrganophosphorus compounds synthesisFrench-language works237,207