(11<i>b</i><i>R</i>)-4,5-Dihydro-3<i>H</i>-dinaphtho[2,1-<i>c</i>:1′,2′-<i>e</i>]Phosphepine Borane
Bibliographic record
Abstract
[1092063-99-4] C22H20BP (MW 326.18) InChI = 1S/C22H17P.BH3/c1-3-7-19-15(5-1)9-11-17-13-23-14-18-12-10-16-6-2-4-8-20(16)22(18)21(17)19;/h1-12,23H,13-14H2;1H3 InChIKey = CDJLGSCFLBPQSK-UHFFFAOYSA-N (precursor to several tertiary 1,1′-binaphthalene-2,2′-bis(methylene)phosphines)1-3 Physical Data: mp 201–205 °C, [α]20D −272 (c 0.5,CHCl3). Solubility: sol in common organic solvents such as THF and toluene. Form Supplied in: white to beige powder or solid. Analysis of Reagent Purity: 1H NMR (CDCl3): δ 7.93–7.86 (m, 4H), 7.51 (dd, J = 8.6, 1.6 Hz, 1H), 7.43–7.39 (m, 2H), 7.27–7.21 (m, 3H), 7.13 (d, J = 8.0 Hz, 1H), 7.08 (d, J = 8.6 Hz, 1H), 5.15 (dm, J = 375 Hz, 1H), 3.03 (ddd, J = 18.7, 13.3, 5.8 Hz, 1H), 2.95 (dt, J = 14.5, 3.6 Hz, 1H), 2.84 (d, J = 13.4 Hz, 1H), 2.67 (ddd, J = 10.5, 12.2, 14.1 Hz, 1H), 0.9–0.0 (br, 3H) 13C{1H} NMR (CD2Cl2) δ 133.92, 133.85, 133.71 (J = 2.6 Hz), 133.53 (J = 2.1 Hz), 133.31, 133.28, 132.38 (J = 11.0 Hz), 132.38 (J = 6.88 Hz, ipso-C), 129.85 (J = 7.7 Hz), 129.55 (J = 1.7 Hz), 129.03 (J = 2.0 Hz), 128.71 (J = 3.4 Hz), 128.63 (J = 1.5 Hz), 128.57 (J = 1.0 Hz), 126.87 (J = 0.8 Hz), 126.73, 126.72, 126.57, 126.54 (J = 1.0 Hz), 126.06 (J = 1.3 Hz, CH), 26.79 (J = 32.5 Hz, CH2), 25.06 (J = 34.3 Hz, CH2). Preparative Methods: (11bR)-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]phosphepine borane (R,S)-1 was prepared by the phosphination of 2,2′-bis[chloromethyl]-1,1′-binaphthyl (R,S)-2 followed by treatment of the resulting secondary phosphine with the borane/THF complex in 71% overall yield (eq 1).1 Alternatively, (S)-1 ([α]20D +195 (c 1.0, CHCl3)) was formed by reducing (S)-4,5-dihydro-5-hydroxy-3H-dinaphtho[1,2-c:2′,1′-e]-phosphepine 5-oxide (S)-3 with phenylsilane and then treating the resulting phosphine with the borane/DMS complex in 43% overall yield (eq 2).2 (1) (2) Purification: flash chromatography on silica gel using CH2Cl2/hexane (1:1) as eluent. Handling, Storage, and Precautions: flammable solid; acute oral toxicity; may cause allergy or asthma symptoms or breathing difficulties if inhaled; may cause eye and skin irritation. Keep container tightly closed and store in a dry and well-ventilated place.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.023 | 0.010 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
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".