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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
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CAS No. : | 5709-98-8 | MDL No. : | MFCD08275445 |
Formula : | C7H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VUSWCWPCANWBFG-LURJTMIESA-N |
M.W : | 126.15 | Pubchem ID : | 736697 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.57 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 34.95 |
TPSA : | 37.3 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) : | -6.17 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | 1.13 |
Log Po/w (SILICOS-IT) : | 0.93 |
Consensus Log Po/w : | 1.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.36 |
Solubility : | 5.55 mg/ml ; 0.044 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.65 |
Solubility : | 2.81 mg/ml ; 0.0223 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.18 |
Solubility : | 83.3 mg/ml ; 0.661 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.91 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P312-P390-P405-P406-P501 | UN#: | 3265 |
Hazard Statements: | H312-H314 | Packing Group: | Ⅲ |
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 |
---|---|---|
84% | Stage #1: at 20℃; for 11 h; Phosphate buffer; Enzymatic reaction |
Synthesis of Intermediate IV:To a stirred suspension of methylester III (5.19 g, 37.0 mmol) in pH 7.00 phosphate buffer solution (520 ml, 0.07 M), PLE (51.2 mg, 1382 units) was added. The pH was kept at 7 by adding NaOH solution (1.0 M) via syringe pump. The reaction was stirred at r.t. until one equivalent of NaOH (37 ml) was used (11 h, TLC-control: petroleum ether/Et20, 1:1). The reaction mixture was transferred into a separation funnel and washed twice with ethyl acetate (2.x.300 ml). The layers were separated and the organic layers were extracted twice with pH 7.00 phosphate buffer solution (2.x.300 ml). The combined aqueous layers were acidified to pH 2 with aqueous HCl (30 ml, 4 M) and extracted three times with ethyl acetate (3.x.400 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo (100 mbar). The crude product was filtered through a short plug of silica affording acid IV as a pale yellowish oil (3.92 g, 84percent). 96.3percent ee. (GC), 94.3percent ee. (rot.), [α]D21+89.12° (c=6.730, MeOH), (Lit. +94.5° (c=7, MeOH), [Acta Chem. Scand., 1970, 24, 2693]). |
84% | Stage #1: at 20℃; Aqueous phosphate buffer; Enzymatic reaction Stage #2: With hydrogenchloride In water |
To a stirred suspension of methylester III (5.19 g, 37.0 mmol) in pH 7.00 phosphate buffer solution (520 ml, 0.07 M), PLE (51.2 mg, 1382 units) was added. The pH was kept at 7 by adding NaOH solution (1.0 M) via syringe pump. The reaction was stirred at r.t. until one equivalent of NaOH (37 ml) was used (11 h, TLC-control: petroleum ether/Et2O, 1:1). The reaction mixture was transferred into a separation funnel and washed twice with ethyl acetate (2.x.300 ml). The layers were separated and the organic layers were extracted twice with pH 7.00 phosphate buffer solution (2.x.300 ml). The combined aqueous layers were acidified to pH 2 with aqueous HCl (30 ml, 4 M) and extracted three times with ethyl acetate (3.x.400 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo (100 mbar). The crude product was filtered through a short plug of silica affording acid IV as a pale yellowish oil (3.92 g, 84percent). 96.3percent ee. (GC), 94.3percent ee. (rot.), [α]D21+89.12° (c=6.730, MeOH), (Lit.+94.5° (c=7, MeOH), [Acta Chem. Scand., 1970, 24, 2693]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 26 h; Stage #2: Acidic aq. solution |
A mixture of the Diels-Alder adduct (1.71 g, 7.2 mmol) and LiOH.H2O (0.81 g, 21.7 mmol) in THF/water (5:4 38 mL) was vigorously stirred at rt for 26 h. THF was removed in vacuo, the aq solution acidified to pH 2 and extracted with n-pentane/DCM (98:2). After drying the organic layer over Na2SO4, the solvent was evaporated under reduced pressure. The residue was purified through column chromatography (eluent 15percent EtOAc/hexane) to afford the acid 5 (0.86 g, 94percent) as a viscous liquid. Rf (15percent EtOAc/hexane) 0.3; [α]D25 +93.7 (c 1, MeOH); (Reported [α]D22 +95 (c 7, MeOH)); νmax (KBr) 2968, 2932, 1720, 1624, 1224, 802 cm-1; δH (300 MHz, CDCl3) 5.80-5.60 (m, 2H), 2.67-2.51 (m, 1H), 2.37-2.22 (m, 2H), 2.21-1.97 (m, 3H), 1.80-1.61 (m, 1H); δC NMR (75 MHz, CDCl3): δ 182.5, 126.6, 124.9, 39.1, 27.1, 24.7, 24.2; m/z (MS-ESI) 149 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26.5 % ee | at 60℃; | Crude (S) -3-cyclohexane-1-carboxylic acid / (1R, 2S) -1-amino-3-cyclohexane-1-carboxylic acid (4.55 g), (1R, 2S) -1-amino-2-indanol (4.30 g) was added to water containing 2-propanol (45 mL), heated to 60 ° C. To dissolve the precipitate. The reaction solution was cooled to 50 ° C. and stirred for 2 hours after crystallization. It was gradually cooled to room temperature at 5 ° C / h and stirred for 12 hours. The precipitate was collected by filtration, washed with 2-propanol (10 mL), and dried under reduced pressure at 40 ° C. to obtain the title compound (5.05 g, 50.9percent, 26.5percent ee) as a white solid |
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