Structure of 153559-48-9
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CAS No. : | 153559-48-9 |
Formula : | C25H30O2 |
M.W : | 362.50 |
SMILES Code : | COC(=O)C1=CC=C(C=C1)C(=C)C1=CC2=C(C=C1C)C(C)(C)CCC2(C)C |
MDL No. : | MFCD16620614 |
InChI Key : | VSMOGQLTPWIBNI-UHFFFAOYSA-N |
Pubchem ID : | 10384066 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 27 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 113.69 |
TPSA ? Topological Polar Surface Area: Calculated from | 26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 4.45 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 7.93 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 6.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 5.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 7.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 6.24 |
Log S (ESOL):? ESOL: Topological method implemented from | -7.15 |
Solubility | 0.0000258 mg/ml ; 0.0000000711 mol/l |
Class? Solubility class: Log S scale | Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from | -8.33 |
Solubility | 0.00000169 mg/ml ; 0.0000000046 mol/l |
Class? Solubility class: Log S scale | Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -8.41 |
Solubility | 0.00000141 mg/ml ; 0.0000000039 mol/l |
Class? Solubility class: Log S scale | Poorly 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) | Yes |
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) | Yes |
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 | -2.88 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 1.0 |
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 | 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) | 3.26 |
* 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 |
---|---|---|
66% | With sodium amide In tetrahydrofuran | Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed PPh3MeBr (1715 mg, 4.80 mmol, 2.50 eq.), THF (10 ml_). This was followed by the addition of KHDMS (1 M) (5.1 ml_, 5.1 1 mmol, 2.66 eq.) dropwise with stirring at -30C. The resulting solution was stirred for 30 min at 0C. To this was added a solution of methyl 4-[(3, 5, 5, 8, 8-pentamethyl-5, 6, 7, 8-tetrahydronaphthalen-2-yl) carbonyl] benzoate (700 mg, 1.92 mmol, 1.00 eq.) in THF (7 ml_) dropwise with stirring at -30C. The resulting solution was stirred for 1 h at 0C. The reaction was then quenched by the addition of 20 ml_ of water at 0C. The resulting solution was extracted with 2x20 ml_ of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1 c20 ml_ of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 480 mg (69%) of methyl 4-[1-(3, 5,5,8, 8-pentamethyl-5, 6,7,8- tetrahydronaphthalen-2-yl)ethenyl]benzoate as a light yellow solid. | |
66% | With sodium amide; In tetrahydrofuran; | Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Rectangular plates of compound 35 were found suitable for X-ray diffraction, and a study was conducted. To complete the synthesis of bexarotene, the Friedel-Crafts acylation of 35, by crude mono-methyl-terephthaloyl chloride (36), gave ketone (37) which was converted to alkene ester(38) by a Wittig reaction, and ester 38 was saponified by potassium hydroxide followed by acidification with aqueous hydrochloric acid to give bexarotene (39) (Scheme 2). | |
Example 3: Preparation of bexaroteneTo suspension of methyl 4-[l-(5,6,7,8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthalenyl)-l- ethenyljbenzoate (100 g) in methanol (1000 ml), 5N aqueous potassium hydroxide (170 ml) was added at 25-30C and the reaction mixture was refluxed for 8 hours. After completion of reaction (monitored by HPLC), reaction mass was cooled to 35-40 C and washed with 50% ethyl acetate: n-heptane mixture (2 x 500 ml). The organic layer was discarded and the aqueous layer was cooled to 10-15 C. Thereafter pH of aqueous layer was adjusted to 1-2 by addition of concentrated hydrochloric acid (100 ml). The resulting mixture was then stirred at 20-25C, stirred for 1 hour and precipitated solid was filtered. The resulting solid was slurry washed with demineralized water (100 ml), centrifuged and dried to give 84.6 g of title compound having purity 98.89 %, none of the impurities C, D, E, F were detected by HPLC |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed Et2Zn (1M) (1.4 ml_, 1.4 mmol, 10.00 eq.), DCM (2 ml_). This was followed by the addition of TFA (157 mg, 1.39 mmol, 10.00 eq.) dropwise with stirring at 0C. The resulting solution was stirred for 30 min at 0C. To this was added CH2I2 (370 mg, 1.4 mmol, 10.00 equiv) dropwise with stirring at 0C. The resulting solution was stirred for 30 min at 0C. To the mixture was added a solution of methyl 4-[1-(3,5,5,8,8-pentamethyl- 5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoate (50 mg, 0.14 mmol, 1.00 equiv) in DCM (1 ml_) dropwise with stirring at 0C. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 20 mL of water at 0C. The solid was filtered out. The resulting solution was extracted with 2x20 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 1 c20 ml of brine and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 10 mg (19%) of methyl 4-[1-(3, 5,5,8, 8-pentamethyl-5, 6,7, 8-tetrahydronaphthalen-2- yl)cyclopropyl]benzoate as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2: Preparation of methyl 4-[l-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2- naphthalenyl)-l-ethenyl]benzoateTo a suspension of methyl triphenylphosphonium bromide (167 g) in toluene (1000 ml) under nitrogen gas atmosphere at 25-30C, potassium hexamethyldisilazide in toluene (0.5 M, 760 ml) was added. The solution was heated to 45-50C, stirred for 30-45 minutes and then cooled to 0-5C. A solution of methyl [4-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate (100 g), dissolved in toluene (600 ml) was slowly added to the reaction mixture and stirred for 2 hours. After completion of the reaction (monitored by HPLC), reaction mixture was poured into 2N hydrochloric acid (1 L). Layers were separated and aqueous layer was extracted with toluene (300 ml). The combined organic layer was washed with water (2 L). Activated carbon (0.05 g) was added to the resulting organic layer and stirred for 15 minutes at 25-30 C. Resulting reaction mass was filtered through hyflo. The filtrate was distilled off under vacuum at 50-55C to give title compound which was stirred in methanol (1 L) to remove triphenylphosphine oxide. The resulting product was filtered and dried to give 80 g of title compound having purity 95.65%, impurity C: 0.56 %, Impurity D: 1.90 %; Impurity E: 0.31%; impurity F: 0.22% by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20℃; | General procedure: Ester prodrugs of BEX and RA were synthesised by adding2.87 mmol of the desired alcohol to 0.287 mmol of BEX or RA. 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.431 mmol) and 4-dimethylaminopyridine(0.057 mmol) were added, and dichloromethane(15 mL) was used as the solvent. The mixture was stirred magneticallyovernight at room temperature. Purification was performed by flashchromatography using a 200-400 mesh silica gel-packed glass columnsand hexane-ethyl acetate 50:2 (v/v) as the mobile phase. Specific detailsfor compounds that were obtained by different synthetic schemesare described in Supplementary Material 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dipotassium hydrogenphosphate; [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triphenylphosphine; In dichloromethane; water; at 20℃; for 48h;Inert atmosphere; Irradiation; | Firstly weighing (20.4 mg, 0 . 15 mmol),photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6(2.3 mg, 0.002 mmol), K2HPO4(7.0 Mg, 0 . 04 mmol),and Ph3P (31.5 mg, 0.12 mmol)are added to a reaction tube, pumping air through the vacuum line three times, in the argon atmosphere, adding DCM/H2O (2.0 ml, 4:1 v/v), then carefully added (36.2 Mg, 0.1 mmol),then put into 5W blue LEDs lamp irradiation, react at room temperature for 48 h.Add 20 ml water, and the DCM extraction (3x 10 ml) the aqueous phase, combined with the organic phase. The organic phase by absolute Na2SO4 after drying and steaming and to remove the solvent, dry sample, column chromatography (300 - 400 item of chromatographic analysis silica gel) (petroleum ether - ethyl acetate) to obtain the product 34.2 mg, Yield 71%. |
Tags: 153559-48-9 synthesis path| 153559-48-9 SDS| 153559-48-9 COA| 153559-48-9 purity| 153559-48-9 application| 153559-48-9 NMR| 153559-48-9 COA| 153559-48-9 structure
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