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CAS No. : | 2930-05-4 | MDL No. : | MFCD00068664 |
Formula : | C10H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QNYBOILAKBSWFG-UHFFFAOYSA-N |
M.W : | 164.20 | Pubchem ID : | 94247 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.88 |
TPSA : | 21.76 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.4 cm/s |
Log Po/w (iLOGP) : | 2.4 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.45 |
Log Po/w (MLOGP) : | 1.17 |
Log Po/w (SILICOS-IT) : | 2.75 |
Consensus Log Po/w : | 1.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.76 |
Solubility : | 2.83 mg/ml ; 0.0172 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.33 |
Solubility : | 7.75 mg/ml ; 0.0472 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.0 |
Solubility : | 0.165 mg/ml ; 0.001 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); water; acetic acid In tetrahydrofuran at 0 - 20℃; for 16 h; | (R,R)-N,N-Bis-(3,5-di-tert-butylsalicyclidene)-1,2-cyclohexanesanediaminocobalt (II) (0.029 g, 0.05 mmol) was added to a mixture of 2-((benzyloxy)methyl)oxirane (1.63 g, 9.91 mmol), AcOH (0.011 mL, 0.198 mmol) and THF (0.15mL). The mixture was cooled to 0 °C and treated with H2O (0.098 mL, 5.45 mmol). The reaction was allowed to reach rt overnight. Purification by flash chromatography using 9:1 hexanes/EtOAc as eluent gave the title compound 17 (0.795g, 4.84 mmol, 48percent) as a colourless oil. Rf: 0.5 (80percent hexanes/EtOAc); [α]D20 +6.03 (c 1.76, CH2Cl2) lit. [α]D+5.4 (c 1.76 in CH2Cl2);2 δH (400 MHz, CDCl3): 7.35-7.25 (5H, m, PhH), 4.61 (1H, d, J = 11.9 Hz, CH2Ph), 4.55 (1H, d, J = 11.9 Hz, CH2Ph), 3.76 (1H, dd, J = 3.1, 11.4 Hz, H-3), 3.44 (1H, dd, J = 5.8, 11.4 Hz, H-3), 3.21-3.16 (1H, m, H-2), 2.812.78 (1H, m, H-1), 2.62-2.60 (1H, m, H-1); δC (100 MHz, CDCl3): 137.8 (C, Ph), 128.4 (2 × CH, Ph), 127.7 (3 × CH, Ph), 73.3 (CH2, CH2Ph), 70.8 (CH2, C-1), 50.8 (CH, C-2), 44.3(CH2, C-3). The spectroscopic data were in agreement with those reported in the literature.2 |
> 99 % ee | at 5 - 20℃; Resolution of racemate | 0.5 mole of racemic 1,2-epoxy compounds were added with 0.4 mole percent of the catalyst prepared in Preparation Example 1 [(1-RR)-(Dibenzoyl-LTA) ] (or Preparation Example 2 [ (1-SS) - (Dibenzoyl- DTA)]) and cooled down to 5 °G Then 5.4 g of water was slowly added here and stirred at 20 °C After fractional distillation under reduced pressure, the target compounds were obtained with more than 99percent ee optical purity |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | at 0 - 20℃; for 30.25 h; | A mixture of 2-(benzyloxymethyl)-oxirane 2 (10.00 g, 61 mmol) and (S,S)-salen Co(III)OAc complex-A (0.09 g, 0.14 mmol) was vigorously stirred for 15 min, then cooled to 0 °C, and water added (0.6 mL, 34 mmol) over a period of 15 min through a micro-syringe. The reaction mixture was stirred at room temperature for 20 h, and then additional (S,S)-salen Co(III)OAc complex-A (0.09 g, 0.14 mmol) was added and stirring was continued for an additional 10 h. The reaction mixture was diluted with ethyl acetate, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/acetone (95:5). The less polar epoxide (R)-3a eluted first as a colorless oil (4.8 g, 48percent), [α]D25=-7.9 (c 0.4, EtOH) {lit.10 [α]D20=-5.8 (c 0.4, EtOH)}; ee > 99percent [chiral HPLC analysis; CHIRALCEL OD-H (250 × 4.6 mm) column; eluent: n-hexane/isopropanol = 90/10; flow rate: 0.5 mL/min; detector: 220 nm [(S)-isomer tR = 15.25 min; (R)-isomer tR = 16.46 min]; IR (CHCl3): νmax 3418, 3020, 2401, 1719, 1603, 1523, 1495, 1421, 1216, 1094, 929, 669 cm−1; 1H NMR (200 MHz, CDCl3): δH = 2.60–2.64 (dd, J = 5.1, 2.7 Hz, 1H), 2.78–2.82 (dd, J = 5.3, 4.2 Hz, 1H), 3.15–3.23 (m, 1H), 3.39–3.48 (dd, J = 11.3, 5.8 Hz, 1H), 3.73–3.81 (dd, J = 11.4, 3.0 Hz, 1H), 4.60 (s, 2H), 7.28–7.37 (m, 5H); 13C NMR (50 MHz, CDCl3): δC = 137.8 (C), 128.4 (CH, 2 carbons), 127.7 (CH, 3 carbons), 73.3 (CH2), 70.7 (CH2), 50.8 (CH), 44.2 (CH2). MS: m/z 187 [M+Na]+, followed by diol (R)-3b as a colorless oil (4.7 g, 43percent); [α]D25=-2.3 (c 6.5, CHCl3) {lit.12 [α]D25=-3.6 (c 6.6, CHCl3)}; IR (CHCl3): νmax 3434, 3020, 1600, 1495, 1215, 1045, 1029, 929, 697 cm−1; 1H NMR (200 MHz, CDCl3): δH = 2.73 (t, J = 5.8 Hz, 1H, OH), 3.13 (d, J = 5 Hz, 1H, OH), 3.51–3.54 (dd, J = 5.4, 2.6 Hz, 2H), 3.57–3.68 (m, 2H), 3.82–3.92 (m, 1H), 4.54 (s, 2H), 7.28–7.39 (m, 5H, Ph); 13C NMR(50 MHz, CDCl3): δC = 137.6 (C), 128.4 (CH, 2 carbons), 127.8 (CH, 3 carbons), 73.5 (CH2), 71.6 (CH2), 70.7 (CH), 63.9 (CH2). |
46% | at 0 - 20℃; for 30 h; Resolution of racemate | A mixture of epoxide 2 (10.00 g, 61 mmol) and (S,S)-Salen Co(III)-(OAc) complex-A (0.09 g, 0.14 mmol) was stirred vigorously for 15min then cooled to 0 °C. H2O (0.6 mL, 34 mmol) was added from a micro syringe over 15 min, and the resulting mixture was stirred at r.t. for 20 h. Additional (S,S)-Salen Co(III)-(OAc) complex-A (0.09g, 0.14 mmol) was then added, and stirring was continued for a further 10 h. The resulting mixture was diluted with EtOAc (30 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, PE–acetone (95:5)]; the less-polar epoxide (R)-3a eluted first, followed by diol (S)-3b.(R)-3a Colorless oil; yield: 4.6 g (46percent); [α]D22 –7.9 (c 0.4, EtOH) {Lit.14[α]D22 –5.8 (c 0.4, EtOH)}. Chiral HPLC: column: CHIRALCEL OD-H (250 × 4.6 mm); eluent: hexane–i-PrOH (90:10); flow rate: 0.5 mL/min; detector: 220nm [(S)-isomer: tR= 15.20 min; (R)-isomer: tR= 16.46 min]; ee >99percent. IR (CHCl3): 3418, 3020, 2401, 1719, 1603, 1523, 1495, 1421, 1216,1094, 929, 669 cm–1. 1H NMR (200 MHz, CDCl3): δ H= 2.61 (dd, J= 5.1, 2.7 Hz, 1 H),2.80 (dd, J= 5.3, 4.2 Hz, 1 H), 3.15–3.23 (m, 1 H), 3.44 (dd, J=11.3, 5.8 Hz, 1 H), 3.77 (dd, J= 11.4, 3.0 Hz, 1 H), 4.60 (s, 2 H),7.28–7.37 (m, 5 H). 13C NMR (50 MHz, CDCl3): δ C= 137.8 (C), 128.4 (CH, 2 C), 127.7(CH, 3 C), 73.3 (CH2), 70.7 (CH2), 50.8 (CH), 44.2 (CH2).MS: m/z = 187 [M + Na]+. [(S)-3b] Colorless oil; yield: 4.7 g (43percent); [α]D22 –2.3 (c 6.5, CHCl3) {Lit.15[α]D22 –3.6 (c 6.6, CHCl3)}. IR (CHCl3): 3434, 3020, 1600, 1495, 1215, 1045, 1029, 929, 697cm–1. 1H NMR (200 MHz, CDCl3): δ H= 2.73 (t, J= 5.8 Hz, 1 H, OH), 3.13 (d, J= 5 Hz, 1 H, OH), 3.52 (dd, J= 5.4, 2.6 Hz, 2 H), 3.57–3.68 (m, 2 H), 3.82–3.92 (m, 1 H), 4.54 (s, 2 H), 7.28–7.39 (m, 5 H,Ph). 13C NMR (50 MHz, CDCl3): δ C= 137.6 (C), 128.4 (CH, 2 C), 127.8(CH, 3 C), 73.5 (CH2), 71.6 (CH2), 70.7 (CH), 63.9 (CH2). |
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