(3a<i>R</i>,7a<i>R</i>)-2-Ethyloctahydro-1<i>H</i>-1,3-dineopentyl-1,3,2-benzodiazaphosphole Oxide
Bibliographic record
Abstract
(1; R1 = neopentyl, R2 = Et) [146397-34-4] C18H37N2OP (MW 328.54) InChI = 1S/C12H23N2OP/c1-4-5-10-16(15)13(2)11-8-6-7-9-12(11)14(16)3/h4-5,11-12H,6-10H2,1-3H3/b5-4+/t11-,12-/m1/s1 InChIKey = UHAPIICFZFIGMI-GKUNOOHESA-N (2; R1 = Me, R2 = allyl) [146098-95-5] C11H21N2OP (MW 228.31) InChI = 1S/C11H21N2OP/c1-4-9-15(14)12(2)10-7-5-6-8-11(10)13(15)3/h4,10-11H,1,5-9H2,2-3H3/t10-,11-/m1/s1 InChIKey = GOZOQKPQKRHZQV-GHMZBOCLSA-N (3; R1 = Me, R2 = Et) [91633-73-7] C10H21N2OP (MW 216.30) InChI = 1S/C10H21N2OP/c1-4-14(13)11(2)9-7-5-6-8-10(9)12(14)3/h9-10H,4-8H2,1-3H3/t9-,10-/m1/s1 InChIKey = MFUIQZXBLJYEND-NXEZZACHSA-N (4; R1 = Me, R2 = Bn) [146098-94-4] C15H23N2OP (MW 278.37) InChI = 1S/C15H23N2OP/c1-16-14-10-6-7-11-15(14)17(2)19(16,18)12-13-8-4-3-5-9-13/h3-5,8-9,14-15H,6-7,10-12H2,1-2H3/t14-,15-/m1/s1 InChIKey = AXPSJUZYRFQKEB-HUUCEWRRSA-N (5; R1 = Me, R2 = CH2CHCHMe) [–] C12H23N2OP (MW 242.34) InChI = 1/C12H23N2OP/c1-4-5-10-16(15)13(2)11-8-6-7-9-12(11)14(16)3/h4-5,11-12H,6-10H2,1-3H3/b5-4+/t11-,12-/m1/s1 InChIKey = UHAPIICFZFIGMI-GKUNOOHEBZ (6; R1 = Bn, R2 = Et) [–] C22H29N2OP (MW 368.50) InChI = 1/C22H29N2OP/c1-2-26(25)23(17-19-11-5-3-6-12-19)21-15-9-10-16-22(21)24(26)18-20-13-7-4-8-14-20/h3-8,11-14,21-22H,2,9-10,15-18H2,1H3/t21-,22-/m1/s1 InChIKey = NBBUYGIHNZUKSO-FGZHOGPDBN (7; R1 = Bn, R2 = Pr) [–] C23H31N2OP (MW 382.53) InChI = 1/C23H31N2OP/c1-2-17-27(26)24(18-20-11-5-3-6-12-20)22-15-9-10-16-23(22)25(27)19-21-13-7-4-8-14-21/h3-8,11-14,22-23H,2,9-10,15-19H2,1H3/t22-,23-/m1/s1 InChIKey = VYGQVQUWSJLUKZ-DHIUTWEWBU (8; R1 = Me, R2 = CH2Cl) [146983-74-6] C9H18ClN2OP (MW 236.71) InChI = 1S/C9H18ClN2OP/c1-11-8-5-3-4-6-9(8)12(2)14(11,13)7-10/h8-9H,3-7H2,1-2H3/t8-,9-/m1/s1 InChIKey = ZKVVRLYRVNIZMC-RKDXNWHRSA-N (chiral α-alkyl bicyclophosphonamides useful for the asymmetric synthesis of alkenes,1-3 of α,α′-substituted phosphonic acids,4 and of α-amino-α-substituted phosphonic acids,5, 6 and for asymmetric conjugate additions of C-allyl and C-crotyl groups to α,β-unsaturated carbonyl compounds7) Physical Data: (1) mp 110–111 °C; [α]D25 −98.8° (c 1.10, CHCl3). (2) mp 45–46 °C; [α]D25 −51.1° (c 1.85, CHCl3). (3) mp 55–56 °C; [α]D25 −98.9° (c 1.48, CHCl3). (4) mp 104–105 °C; [α]D25 −109.6° (c 1.17, CHCl3). (6) mp 153–154 °C; [α]D25 −68.2° (c 1.18, CHCl3). (7) mp 117 °C; [α]D25 −66.0° (c 1.02, CHCl3). (8) mp 84 °C; [α]D25 −109.8° (c 1.0, CHCl3). Solubility: sol chlorinated and dipolar aprotic solvents, and hydrocarbon solvents in some cases. Gradual hydrolysis in protic media. Form Supplied in: colorless crystalline or waxy solids. Preparative Method: 3 to a solution of (1R,2R)-N,N′-dineopentyl-1,2-diaminocyclohexane (1.37 g, 5.40 mmol) and triethylamine (2.3 mL, 48.5 mmol) in 25 mL of benzene is added ethylphosphoryl dichloride (0.89 g, 6.06 mmol). The suspension is heated to reflux for 80 h, the salts are filtered, and the filtrate is washed successively with 10% aq HCl (2 × 10 mL), aq saturated NaHCO3, and water. Drying, evaporation, and chromatographic separation (EtOAc) gives the title compound (1.1 g, 62%) as a crystalline solid, mp 110–111 °C (hexanes). Single crystal X-ray analysis confirmed the structure. For an alternative synthesis of related compounds, see Kueller and Spilling.8 Other 2-alkyl derivatives can be similarly prepared.1-4 Handling, Storage, and Precautions: crystalline reagents are stable when stored under argon at 0 °C for several months.
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 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 | 0.009 |
| Meta-epidemiology (narrow) | 0.005 | 0.006 |
| Meta-epidemiology (broad) | 0.008 | 0.004 |
| Bibliometrics | 0.001 | 0.002 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.007 | 0.002 |
| Research integrity | 0.005 | 0.003 |
| Insufficient payload (model declined to judge) | 0.076 | 0.005 |
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".