Structure of 939-97-9
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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.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 939-97-9 |
Formula : | C11H14O |
M.W : | 162.23 |
SMILES Code : | O=CC1=CC=C(C(C)(C)C)C=C1 |
MDL No. : | MFCD00035742 |
InChI Key : | OTXINXDGSUFPNU-UHFFFAOYSA-N |
Pubchem ID : | 70324 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H360-H302-H317-H410 |
Precautionary Statements: | P201-P202-P261-P264-P270-P272-P273-P280-P301+P310+P330-P302+P352-P308+P313-P333+P313-P391-P405-P501 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.36 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.8 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.69 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.87 |
Solubility | 0.217 mg/ml ; 0.00134 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.86 |
Solubility | 0.226 mg/ml ; 0.00139 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.54 |
Solubility | 0.0463 mg/ml ; 0.000285 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 |
Yes |
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) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
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 |
-5.27 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 |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
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 |
1.0 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) |
1.0 |
* 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 |
---|---|---|
Example 232 3-(4-tert-Butyl-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-tert-butylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 195-197 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With sodium ethanolate; In ethanol; at 80℃; for 0.833333h; | General procedure: In a round bottom flask 1 eq. of dimedone, 1 eq of the desired aldehyde and 1 eq of <strong>[57508-48-2]ethyl 3-amino-3-iminopropionate hydrochloride</strong> were suspended in dry EtOH (2.5 mL/mmol) and heated at 80 C. To this solution 1 eq of a 0.5 M sodium ethanolate solution was added over the period of 20 min. After heating for further 30 min under reflux the reaction was cooled to 0 C and water (40 mL/mmol) was added. The aqueous solution was extracted with EtOAc (5×20 mL/mmol). The combined organic layers were washed with brine, dried with MgSO4 and the solvent was evaporated under reduced pressure. The crude material was purified by recrystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Compound S1 was synthesized following a published procedure with slight modifications. 2Na2S·9H2O (1.5 g, 6.25 mmol) was added to a mixture of sulfur (1.0 g, 31.2 mmol) and3-(tert-butyl)aniline (5.6 g, 37.5 mmol) in DMF (25 mL). The suspension was stirred at 115 °C for0.5 h under nitrogen. Afterwards, the mixture was cooled to room temperature,4-(tert-butyl)benzaldehyde (4.1 g, 25 mmol) was added and the mixture was stirred at 115 °C for 24h under nitrogen. After cooling to room temperature, the resulting solution was quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate. The organic fraction was thoroughly washed with water and dried with Na2SO4. After concentration, the residue was purifiedby silica gel column (n-hexane/EtOAc = 40:1) to yield thioamide S1 as a yellow solid (4.72 g,58percent).1H NMR (300 MHz, CDCl3) delta 9.06 (brs, 1H), 7.83-7.76 (m, 3H), 7.72-7.62 (m, 1H), 7.51-7.27 (m,4H), 1.35 (s, 18H).13C NMR (75 MHz, CDCl3) delta 197.8, 154.7, 152.3, 140.6, 138.9, 128.5, 126.5, 125.5, 123.7, 120.6,120.5, 34.83, 34.78, 31.2, 31.1.IR (film): nu (cm1) 3173, 2957, 2867, 1595, 1512, 1472, 1419, 1336, 1274, 1240, 1199, 1112, 999,907, 843, 747, 701.HRMS (ESI, m/z) calcd for C21H27NSNa [M+Na]+: 348.1756, found: 348.1755. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h; | General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
A202849 [6136-71-6]
1-(3-(tert-Butyl)phenyl)ethanone
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