Structure of 7287-82-3
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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. : | 7287-82-3 |
Formula : | C9H12O |
M.W : | 136.19 |
SMILES Code : | CC(O)C1=CC=CC=C1C |
MDL No. : | MFCD00046632 |
Boiling Point : | No data available |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.34 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.77 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.72 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.02 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.18 |
Solubility | 0.905 mg/ml ; 0.00665 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.81 |
Solubility | 2.1 mg/ml ; 0.0154 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.61 |
Solubility | 0.331 mg/ml ; 0.00243 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) |
Yes |
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 |
-5.87 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 |
0.0 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) |
1.16 |
* 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 |
---|---|---|
With 1H-imidazole; [bis(acetoxy)iodo]benzene; C84H72ClFeN4O12S4(4-)*4Na(1+); In methanol; water; for 1h;Inert atmosphere; | General procedure: Iron porphyrin complex 1 (1.6 mg, 1 mumol) and imidazole (0.68 mg, 10 mumol) was placed in a test tube under argon. Then, 0.8 ml of distilled methanol and 0.2 ml H2O were added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2, (32 mg, 100 mumol) in 0.2 ml methanol was added over a period of 45 mn. After 1 h, the mixture was analysed by GC for oxidation yield, 46%, based on oxidant, and for epoxide enantiomeric excess, 75%. Polarimetric measurement of the oxidation product determined that (S)-(-)-1-phenylethanol was formed in excess. In addition to expected phenylethanol, acetophenone was also observed.The reaction and analysis of the other susbtrates in Table 1 were carried out in a manner identical with that used for ethylbenzene oxidation except for indane and tetrahydronaphtalene. In the latter case, enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol=95/5; flow rate=0.5 ml min-1; wavelength=220 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; ferrocenium(III) tetrafluoroborate; ethylbenzene dehydrogenase; In water; tert-butyl alcohol; at 30℃;Enzymatic reaction; | General procedure: 2.1. Sample preparation Ethylbenzene dehydrogenase was purified from ethylbenzene-grown A. aromaticum cells as previously described [11,23]. The enzyme assays were routinely conducted at an optimum pH of 7.5 at 30 C in 20 ml of 100 mM Tris/HCl containing 200 muM ferrocenium (III) tetrafluoroborate and ethylbenzene dehydrogenase (100-300 mul of app. 1 mg/ml protein solution). The reactions were initiated by adding 100 mul of a stock solution of the respective substrate in tert-butanol (a list of substrates, their purities and producers is available in the Supporting Information). After an overnight incubation, the reaction mixtures were extracted from the water phase by solid-phase extraction using either C18 Polar Plus (J.T. Baker from Avantor Performance Materials, US) or polystyrene/divinylbenzene (PS/DVB) copolymers solid phase extraction (SPE) columns (Strata-X from Phenomenex, US or the equivalent Chromabond HR-X from Macherey-Nagel, Germany), which were eluted with 0.5 ml of isopropanol. The only exception to the procedure was the 2-ethyl-1H-pyrrole reaction mixtures (22). Due to the high polarity of the product derived from this compound, we were unable to concentrate the sample and exchange the solvent by SPE. Therefore, the enzyme was precipitated by the addition of 50% methanol, and it was removed by centrifugation. The supernatant was directly analyzed by non-chiral reversed-phase (RP)-LC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [bis(acetoxy)iodo]benzene; chloro(5,10,15,20-tetrakis-(10-nitro-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-dimethanoanthracen-9-yl)porphyrin) iron(III); In methanol; dichloromethane; water; for 2h;Inert atmosphere; | General procedure: Iron porphyrin complex 5 (1.2 mg 1 mumol) and imidazole (0.34 mg, 10 mumol) were placed in a test tube under argon. Then, 1 ml of distilled CH2Cl2/MeOH/H2O mixture (0.5:0.4:0.1) was added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2 (32 mg, 100 mumol) in 0.1 ml CH2Cl2 was added over a period of 1 h with a syringe-pump. After the addition of all the PhI(OAc)2, the reaction mixture was allowed to stir for an additional 1 h. The mixture was analyzed by GC for oxidation yield based on oxidant, 41 %, alcohol/ketone ratio, 83:17, and alcohol enantiomeric excess, 68 % (conditions used: 80 C (1 min), 1 C min-1 80-120 C, 2.5 C min-1 120-180 C). Polarimetric measurement of the oxidation product determined that (R)-(+)-1-phenyl ethanol was formed in excess. The reaction and analysis of the other substrates and catalysts in Table 3 were carried out in an identical manner with that used for ethylbenzene oxidation. Except for indane, the enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol 95:5; flow rate: 0.5 ml min-1, detection: 220nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With C20H26B10Cl2FeN6; dihydrogen peroxide; In methanol; at 20℃; for 8h; | Dissolve 2-methylethylbenzene (1.0 mmol), iron complex 1 (0.02 mmol) and H2O2 (1.5 mmol) in 2 mL of methanol and react at room temperature for 8 hours.After the reaction, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding product C9H12O was obtained (93% yield). |