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CAS No. : | 171877-39-7 | MDL No. : | MFCD06658216 |
Formula : | C10H11NS2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SLDUGQISGRPGAW-VIFPVBQESA-N |
M.W : | 209.33 | Pubchem ID : | 11458470 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 65.81 |
TPSA : | 69.42 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.53 cm/s |
Log Po/w (iLOGP) : | 2.13 |
Log Po/w (XLOGP3) : | 2.88 |
Log Po/w (WLOGP) : | 1.84 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 3.92 |
Consensus Log Po/w : | 2.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.16 |
Solubility : | 0.144 mg/ml ; 0.000689 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.0 |
Solubility : | 0.021 mg/ml ; 0.000101 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.66 |
Solubility : | 0.0456 mg/ml ; 0.000218 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.65 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
81% | With carbon disulfide; potassium hydroxide In water at 100℃; for 16 h; | The crude oxazolidinethione was dissolved in CS2 (364.0 mL, 5.95 mol) and aqueous IN KOH (5.95 L) was added. The mixture was warmed to 100°C. After stirring at 100°C for 16 h, the mixture was cooled to rt and was extracted with CH2C12 (3 x 3 L). The organic layers were combined, dried over Na2S04, flushed with 1 : 1 hexanes/EtOAc (2 L) through a plug of Si02 (800 g), and concentrated via rotary evaporation to afford a crude product. Pure S2 (201.5 g, 81percent) was obtained by flash chromatography eluting with a gradient of hexanes to 1 : 1 hexanes/EtOAc. [0159] Auxilary S2: TLC (1 : 1 hexanes/EtOAc): Rf = 0.31; 1H NMR (CDC13, 500 MHz) δ 8.36 (bs, 1H), 7.32 (m, 2H), 7.26 (m, 1H), 7.18 (m, 2H), 4.46 (dd, J = 7.5, 15.0 Hz, 1H), 3.50 (dt, J = 7.9, 11.5 Hz, 1H), 3.25 (dt, J = 7.2, 11.5 Hz, 1H), 3.04 (m, 1H), 2.93 (m, 1H); 13C NMR (CDC13, 125 MHz) δ 200.5, 135.7, 129.0, 128.9, 127.2, 65.1, 39.7, 37.8; FTIR (film) vmax 3154, 1602, 1495, 1437, 1327, 1297, 1279, 1233, 1204, 1040, 1008, 957, 743 cm-1; HR-ESI- MS m/z calcd. For C10H11NS2 [M]+: 209.0333, found 209.0342 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76 % de | at -78℃; for 1.33333 h; Inert atmosphere | To a freshly flame dried 50 mL two neck round-bottom flask, was dissolved 1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl) ethanone] 9(1.0 g, 4 mmol) in 20 mL of anhydrous CH2Cl2 under N2 atmosphere. TiCl4 (0.76 g, 4 mmol, 1M) in CH2Cl2 was added to the above bright yellow solution which was previously cooled to 0 oC and the suspension was stirred at the same temperature for 15 min. To this resulting homogeneous orange solution, DIPEA (0.62 g, 4.8 mmol) was added at 0 oC. The brick-red colour solution was allowed to stir at same temperature for 30 min. This titanium enolate solution was recooled to -78 °C and stirring continued for 20 min. A solution of aldehyde 5 (0.5 g, 4 mmol) in dichloromethane (3 mL) was transferred via cannula to the reaction mixture at -78 °C. After being stirred for 1 h, the reaction mixture was quenched by pouring into 15 mL of half saturated aq. NH4Cl solution. Reaction mixture was warmed to room temperature and diluted with dichloromethane (10 mL). The organic layer was separated and aqueous portion was extracted with CH2Cl2 (3 x 5 mL). The combined organic layers were washed with brine solution (25 mL), dried over Na2SO4 and concentrated in vacuo to afford the mixture of aldol adducts 10 and 10a as pale yellow liquid (0.97 g, 65percent yield). The diastereomeric ratio of the crude product (88:12) was determined by HPLC (C18 column, 6:4 acetonitrile and water as eluents). The diastereomers were separated by silica gel column chromatography (8percent EtOAc in hexanes) to provide the syn aldol adduct 10 (53percent) as major diastereomer. [á]20D = +88.2 (c 2.0, CHCl3). IR (KBr): ímax3445, 2924, 1681, 1494, 1260, 1041, 744, 701 cm-1.1H NMR (300 MHz, CDCl3): ä7.36-7.31 (m, 2H), 7.30-7.24 (m, 3H), 5.51-5.43 (m, 1H), 5.42-5.34 (m, 2H), 5.30 (d, J = 7.8 Hz, 1H), 4.93 (dt, J = 2.9, 8.8 Hz, 1H), 3.52 (dd, J= 2.9, 17.6 Hz, 1H), 3.44-3.37 (m, 1H), 3.31 (q, J = 8.8, 1H), 3.05 (m, 1H), 2.90 (d, J = 10.7 Hz, 1H) 2.79 (dq, J = 14.7, 5.8 Hz, 2H), 2.54 (bs, 1H), 1.73 (s, 3H), 1.67 (d, J = 7.8 Hz, 3H). 13C NMR (75 MHz, CDCl3): ä201.2, 172.7, 136.3, 129.4, 129.1, 128.9, 128.8, 127.4, 127.2, 68.3, 65.0, 40.1, 38.3, 36.7, 32.0, 17.8, 16.7. MS (ESI): m/z 398 (100) [M+Na]+. HRMS (ESI): calcd for C20H25NNaO2S2 [M+Na]+: 398.1219, found : 398.1250. |
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