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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 80522-42-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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Search for reports by entering the product batch number.
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CAS No. : | 80522-42-5 |
Formula : | C10H21F3O3SSi |
M.W : | 306.42 |
SMILES Code : | O=S(C(F)(F)F)(O[Si](C(C)C)(C(C)C)C(C)C)=O |
MDL No. : | MFCD00009913 |
InChI Key : | LHJCZOXMCGQVDQ-UHFFFAOYSA-N |
Pubchem ID : | 2724529 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 68.29 |
TPSA ? Topological Polar Surface Area: Calculated from |
51.75 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.07 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.7 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.6 |
Solubility | 0.00768 mg/ml ; 0.0000251 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-6.0 |
Solubility | 0.000304 mg/ml ; 0.000000993 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.99 |
Solubility | 0.312 mg/ml ; 0.00102 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.5 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.26 |
* 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 |
---|---|---|
79% | With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; | To a solution of <strong>[60211-57-6](3,5-dichlorophenyl)methanol</strong> (10.0 g, 56.5 mmol) in methylene chloride (100 mL) at 0 0C was added 2,6-lutidine (16.4 mL, 141 mmol) followed by triisopropylsilyl triflate (19.7 mL, 73.4 mmol), and was stirred at 0 0C for 2 hours. The reaction was diluted with water and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel, eluting with hexane to provide the desired product (14.8 g, 79%). LC/MS: 333 (M+H)+, 1H NMR (CDCl3) delta 7.23 (s, 3H), 4.78 (s, 2H), 1.18 (m, 3H), 1.03 (s, 18H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In dichloromethane; | Example 156, Part A 6-Bromo-2,3-dihydro-1-[[tris(1-methylethyl)silyl]oxy]-1H-indene To <strong>[75476-86-7]6-Bromo-2,3-dihydro-1H-inden-1-ol</strong> (300 mg, 1.41 mmol) in CH2Cl2 (4 mL) was added 2,6-lutidine (151 muL, 1.4 mmol) followed by triisopropylsilyltriflate (378 muL, 1.41 mmol) at room temperature. The reaction was stirred for 30 min then added to 1N HCl and extracted. The organic layer was washed with saturated sodium bicarbonate then brine and dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; | At r.t. a solution of FmocONSu (3.37 g, 10.0 mmol) in 25 mL of Dioxane12 is added over 1h to a solution of L-threonine (1.19 g, 10.0 mmol) and Na2CO3 (1.06 g, 10.0 mmol) in 10 mL Dioxane and 25 mL water. The resulting suspension is stirred overnight and becomes clear. The solvent is evaporated in vacuo and the product is precipitated with 1M HClaq. at pH 4, filtered, washed with water and dissolved in EtOAc. The organic phase is dried (Na2SO4) and evaporated to yield the product quantitatively as a white solid which does not need any further purification. Under argon atmosphere Fmoc-threonine (2.67 g, 7.80 mmol) is dissolved in 32 mL dry MeOH. Then Cs2CO3 (1.40 g, 4.30 mmol) is added.11 After 15 min the solvent is evaporated and the resulting solid is three times suspended in CH2Cl2 and evaporated to remove all the MeOH. The Cs-salt is then suspended in 36 mL of dry DMF under argon atmosphere and stirred with benzylbromide (1.02 mL, 1.47 g, 8.60 mmol) over night at r.t. After evaporation of the solvent in vacuo, the residue is partitioned between water and CH2Cl2. The water phase is subsequently extracted two times with EtOAc. The combined organic phases are dried (Na2SO4) and evaporated. The crude product is purified either by recrystallisation from EtOAc or by silica column chromatography (cyclohexane/EtOAc 4 : 1) to get Fmoc-threoninebenzylester (3.07 g, 7.10 mmol, 91%, Rf = 0.17 (cyclohexane/EtOAc 3 : 1)) as a white solid. The Fmoc-threoninebenzylester (2.16 g, 5.00 mmol) is dissolved in 48 mL dry CH2Cl2 under argon atmosphere. The solution is cooled to 0C and NEt3 (770 muL, 560 mg, 5.50 mmol) and Triisopropylsilyltriflat (1.42 mL, 1.61 g, 5.25 mmol) is added subsequently.12 The mixture is allowed to warm to r.t. and is stirred 1h. Then 30 mL of dilute K2CO3- solution is added. The phases are separated and the water phase is extracted two times with CH2Cl2. The combined organic phases are dried (Na2SO4) and evaporated. The crude product is purified by silica column chromatography (cyclohexane/EtOAc 10 : 1) to get Fmoc(OTIPS)benzylester (2.47 g, 4.20 mmol, 84%, Rf = 0.61 (cyclohexane/EtOAc 3 : 1)) as a colourless oil. Fmoc(OTIPS)benzylester (0.87 g, 1.48 mmol) is dissolved in 7.4 mL dry CH2Cl2 under argon atmosphere. The solution is cooled to 0C and 7.4 mL of 40% (v/v) Piperidine solution in dry CH2Cl2 are added dropwise.13 After 15 min of stirring at 0C, the mixture is concentrated in vacuo at 25C to an oil and put immediately onto the silica column (cyclohexane/EtOAc 5 : 1 + 0.5% NEt3, elution of product with 1 : 1 + 0.5% NEt3). Yield of the title compound 17d is 0.44 g (1.20 mmol, 81%) as a colourless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere; | To a solution of 20 (0.9 g, 5.3 mmol) in dry DCM (15 mL) under N2 atm was added TEA (1.3 mL, 9.0 mmol), followed by triisopropyl triflate (1.7 mL, 6.4 mmol). The reaction was stirred at room temperature for 2h, washed with cold saturated aqueous NaHCO3 (2×10 mL), dried over anhydrous Na2SO4, concentrated by rotary evaportation, and purified by column chromatography to give triisopropyl((6-methyl-3,4-dihydronaphthalen-1-yl)oxy)silane (17b) (84) 1H NMR (600 MHz, CDCl3) delta 7.41 (d, J=12.0 Hz, 1H), 7.01 (d, J=6.0 Hz, 1H), 6.94 (s, 1H), 5.11 (t, J=6.0 Hz, 1H), 2.71 (t, J=12.0 Hz, 2H), 2.32 (s, 3H), 2.29-2.26 (m, 2H), 1.30-1.24 (m, 3H), 1.12 (d, J=12.0 Hz, 18H). GC-MS (ES) for C20H32OSi [M]+ =316. |