(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 distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.002 | 0.006 |
| Meta-epidemiology (narrow) | 0.003 | 0.003 |
| Meta-epidemiology (broad) | 0.005 | 0.003 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.004 | 0.001 |
| Research integrity | 0.003 | 0.001 |
| Insufficient payload (model declined to judge) | 0.064 | 0.002 |
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; both teacher heads agree on what is shown here.
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".