Structure of 330-93-8
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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. : | 330-93-8 |
Formula : | C12H8F2O |
M.W : | 206.19 |
SMILES Code : | FC1=CC=C(OC2=CC=C(F)C=C2)C=C1 |
MDL No. : | MFCD00013552 |
InChI Key : | UUKHFGSOCZLVJO-UHFFFAOYSA-N |
Pubchem ID : | 67615 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.92 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.6 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.86 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.66 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.42 |
Solubility | 0.0788 mg/ml ; 0.000382 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.78 |
Solubility | 0.346 mg/ml ; 0.00168 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.22 |
Solubility | 0.00125 mg/ml ; 0.00000604 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.48 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 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.72 |
* 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 |
---|---|---|
...presented by the following formula (4) which can respectively correspond to the formula (1) can be obtained. (D) Fluorine substituted aromatic compound represented by the formula (4) corresponding to the hydroxy compound wherein X1 is a substituent of the group (a) in the formula(1): ... 4-trifluoromethoxy-4'-fluorodiphenylsulfide, 4-trichloromethoxy-4'-fluorodiphenylsulfide, 2,2'-difluorodiphenylether, 2,3'-difluorodiphenylether, 2,4'-difluorodiphenylether, 3,3'-difluorodiphenylether, 3,4'-difluorodiphenylether, 4,4'-difluorodiphenylether, 4-methyl-4'-fluorodiphenylether, 4-methoxy-4'-fluorodiphenylether, 4-phenyl-4'-fluorodiphenylether, 4-nitro-4'-fluorodiphenylether, 4-cyano-4'-fluorodiphenylether, 4-chloro-4'-fluorodiphenylether, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; acetic acid; dimethyl sulfoxide; | EXAMPLE 9 (+-) cis-1-Amino-2-[4-(4-fluorophenoxy)phenoxymethyl]cyclopentane hydrochloride A solution of (+-) cis-1-amino-2-hydroxymethylcyclopentane (0.46 g, 4.0 mol) in dry dimethyl sulfoxide (12 ml), was treated with sodium hydride (0.144 g of an 80% dispersion in oil; 4.8 mmol). After stirring for 3 h at room temperature under argon a solution of <strong>[330-93-8]bis-(4-fluorophenyl)-ether</strong> (1.65g, 8.0 mmol) in dimethyl sulfoxide (2 ml) was added. The mixture was heated to 60 C. and held at this temperature for 19 h. The reaction was quenched at ice temperature with glacial acetic acid (0.27 ml, 4.8 mmol) and then worked up as described in Example 5. Purification by chromatography on silica gel eluding with 0-5% ethanol in diethyl ether afforded an oil. The product was extracted into diethyl ether-hexane, and insoluble impurities were discarded. Treatment with ethereal HCl produced the hydrochloride salt which was crystallized to give the title compound as a white solid (0.56 g) m.p. 170-171 C. (from methanol/diethyl ether). 1 H Nmr (DMSO-d6) delta: 1.50-2.10 (6H, m), 2.47 (1H, m), 3.63 (1H, m), 3.97 (1H, m), 4.12 (1H, m), 6.96 (6H, m), 7.18 (2H, m), 8.18 (3H, br s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride; cobalt acetylacetonate; sodium t-butanolate; In toluene; at 140℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: To a dried 40mL tube equipped with a magnetic stirrer, 0.2mmol of substrate, 0.5mmol of LiAlH4, 0.03mmol of Co(acac)2, 0.5mmol of t-BuONa, and 2 or 1.5mL of toluene were added under nitrogen atmosphere. The reaction tube was sealed and placed in a constant-temperature oil bath set at 140C to perform the reaction for 24h (note: the pressure tube was required because the pressure of the reaction system was more than the standard atmospheric pressure). Once the reaction time was reached, the mixture was cooled to room temperature. The mixture was then acidified to pH5-6 with 2M hydrochloric acid. GC analysis of the mixture provided the GC yields of the products (note: in order to minimize the analysis error, the mixture after the reaction was not purified or concentrated). The reductive cleavage products were identified by GC-MS data. Some products were purified by column chromatography, and identified by 1H-NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In N,N-dimethyl-formamide; at 150℃; for 24h; | Chemical compound4-fluorophenol (2mmol)With the compound 4-fluoroiodobenzene (6mmol)Dissolve in N, N-dimethylformamide (20mL) solution,After adding sodium carbonate, it was stirred at 150 C for 24h.The formed compound was extracted with ethyl acetate and washed with saturated brine to obtain compound 1a |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With ammonium hydroxide; sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; In 5,5-dimethyl-1,3-cyclohexadiene; at 150℃; for 36h;Inert atmosphere; | Put a moderate stirrer in a dry reaction tube (20 ml), add palladium hydroxide / carbon (20 mol%),NaBH4 (2 times equivalent), then the reaction tube is evacuated, filled with argon, repeated three times, dissolved in an argon atmosphereA solution of <strong>[330-93-8]bis(4-fluorophenyl)ether</strong> (0.2 mmol) and aqueous ammonia (1 mmol) in xylene was slowly added to the reaction tube with a syringe, which was reversed.The tube should be placed in a 150 C oil bath and heated and stirred. After 36 hours, the reaction was stopped and the reaction tube was taken out of the oil bath.It was naturally cooled to room temperature, diluted with ethyl acetate, and then the reaction liquid was filtered with celite, and the yield of the filtrate was determined by gas phase detection.62%. The filtrate was concentrated and separated by an activated thin layer chromatography chromatography plate (eluent: n-hexane/ethyl acetate = 30/1).The final product 3a is obtained after separation. Product 3a (yield: 48%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In N,N-dimethyl-formamide; at 60℃; for 36h; | Compound 1a (2mmol) and carbazole(12mmol) dissolved in N, N-dimethylformamide (30mL) solution, in 1,Stir at 60 C for 36h. The precipitate formed is separated by vacuum suction filtration,It was washed with saturated saline and recrystallized in acetone to obtain compound 3. |
A119760 [332-48-9]
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