Structure of 707-37-9
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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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CAS No. : | 707-37-9 |
Formula : | C12H20O |
M.W : | 180.29 |
SMILES Code : | OC12CC3(C)CC(C2)(C)CC(C3)C1 |
MDL No. : | MFCD00074775 |
InChI Key : | LBWCITVBZLTEKW-UHFFFAOYSA-N |
Pubchem ID : | 265793 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.47 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.73 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.0 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.19 |
Solubility | 0.117 mg/ml ; 0.000649 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.65 |
Solubility | 0.0404 mg/ml ; 0.000224 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.58 |
Solubility | 0.471 mg/ml ; 0.00261 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) |
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 |
-4.89 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.89 |
* 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 |
---|---|---|
48.7%Chromat. | With ozone; In dichloromethane; at 2 - 10℃; for 10h; | Into a 300 mL round bottom flask, 3.28 g of DMA and 240 mL of dichloromethane were placed, a stirrer was put, and stirring was carried out using a magnetic stirrer.The flask was equipped with a thermometer and a glass gas introduction pipe, and the gas was passed through a cooling pipe, passed through a water trap, an ozone decomposition column, and exhausted. Cooling was carried out in the range of 2 to 10 C., and reaction was carried out while blowing ozone-containing gas through a glass tube.Conditions of the ozone generator are as follows. Ozone generator IO-4-2 made by Japan Ozone is flowed with oxygen at 6 L / h, the discharge voltage is 60 V, the discharge current is 2.5 A, and the concentration of the ozone-containing gas is measured Although it corresponds to DMA, it corresponds to a condition to distribute a large excess of ozone.A small amount of sampling was carried out every hour after starting the reaction, and the reaction was continued while tracking the composition change by GC-FID analysis.When 10 hours passed, DMA was 40.2 area% by area percentage method, DMAO was 47.8 area%, DMAD was 1.9 area%, with respect to the sum of peak areas other than acetic acid used as a solvent.When <strong>[702-79-4]1,3-dimethyladamantane</strong> was oxidized with ozone in dichloromethane solvent, the reaction was difficult to proceed.Google Translate for Business:Translator ToolkitWebsite TranslatorGlobal Mark |
Take 50g of <strong>[702-79-4]1,3-dimethyl adamantane</strong> into a three-neck bottle, Add 100ml of 1,2-dichloroethane, 53.5 g of bromine was added dropwise at room temperature. After the dropwise addition, the reaction solution was heated to 40 C for 2 hours. Add 80ml of water in one time, heat to 80 C and cool to room temperature during the reaction. Phase,The organic phase was washed with 5% sodium bisulfite. Wash with saturated sodium chloride solution, dry, A solution of 3,5-dimethyl-1-adamantanol in 1,2-dichloroethane was obtained by filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.3%Chromat.; 68.4%Chromat. | With N-hydroxyphthalimide; cobalt(II) acetate; ozone; acetic acid; at 38 - 46℃; for 8h; | In a 100 mL round bottom flask, 12.9 g of DMA, 0.12 g of cobalt (II) acetate tetrahydrate, 1.02 g of NHPI and 52.45 g of acetic acid were charged, a stirrer was placed, and stirred Was carried out.The flask was equipped with a thermometer and a glass gas introduction pipe, and the gas was passed through a cooling pipe, passed through a water trap, an ozone decomposition column, and exhausted.Heating to 40 C. was carried out and a reaction was carried out while maintaining the temperature in the range of 38 to 46 C. while blowing ozone-containing gas containing ozone equivalent to 4.9 g / h through a glass tube.A small amount of sampling was carried out at the time when 2, 4, 6, 8 hours passed since the start of the reaction, and the reaction was continued while tracking the composition change by GC-FID analysis.After 8 hours, DMAO was 7.3 area% by area percentage method, DMAD was 68.4 area%, and DMA was not detected with respect to the sum of peak areas other than acetic acid used for solvent. |
50.1%Chromat.; 21%Chromat. | With ozone; acetic acid; at 10 - 20℃; for 15h; | The same procedure as in Comparative Example 1 was carried out except that 130 mL of acetic acid containing 50% of water was charged as a solvent and the reaction was carried out while maintaining the reaction temperature in the range of 10 to 20 C.After 5, 10, and 15 hours from the start of the reaction, a small amount of sampling was carried out and the reaction was continued while tracking the composition change by GC-FID analysis.When 15 hours passed, DMA was 0.7 area% by area percentage method, DMAO was 50.1 area%, DMAD was 21.0 area%, with respect to the sum of peak areas other than acetic acid used for the solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With acetic acid; | Example D8 A mixture of 1.64 grams (10 millimoles) of <strong>[702-79-4]1,3-dimethyladamantane</strong>, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 10 milliliters of acetic acid was stirred under oxygen atmosphere at a temperature of 70 C. for six hours. As a result, with a transformation rate for <strong>[702-79-4]1,3-dimethyladamantane</strong> of 99%, 1-hydroxy-3,5-dimethyladamantane (yield 39%), and 1,3-dihydroxy-5,7-dimethyladamantane (yield 58%) were obtained. The selectivity for the alcohols was 97%. |