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[ CAS No. 230615-51-7 ] {[proInfo.proName]}

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Chemical Structure| 230615-51-7
Chemical Structure| 230615-51-7
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Quality Control of [ 230615-51-7 ]

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Product Details of [ 230615-51-7 ]

CAS No. :230615-51-7 MDL No. :MFCD11042282
Formula : C13H12F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :LMOTUASGGOAXPT-UHFFFAOYSA-N
M.W : 255.24 Pubchem ID :21864732
Synonyms :

Calculated chemistry of [ 230615-51-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.38
TPSA : 20.31 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 3.54
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.14
Solubility : 0.183 mg/ml ; 0.000718 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.607 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.49
Solubility : 0.082 mg/ml ; 0.000321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.61

Safety of [ 230615-51-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 230615-51-7 ]

* 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.

  • Downstream synthetic route of [ 230615-51-7 ]

[ 230615-51-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 230615-51-7 ]
  • [ 1493-13-6 ]
  • [ 230615-53-9 ]
YieldReaction ConditionsOperation in experiment
With nitric acid; In dichloromethane; at 0 - 20℃; Trifluoromethane sulfonic acid (19.8g) was dissolved in CH2CI2 (275ml) and cooled to 00C. Fuming HNO3 (2.8ml) was added dropwise. The solution was cloudy for a brief period, then went to a clear yellow solution again. In a separate vessel, 3-(trifluoroacetyl)-2,3,4,5- tetrahydro-1 H-1 ,5-methano-3-benzazepine (15.3g) was dissolved in CH2CI2 (350ml) and transferred to an addition funnel. This solution was added dropwise over ~1 hour. The reaction temperature was maintained at 0-50C throughout the addition. Once addition was complete, the pot was kept at 0-50C for 2 hours, slowly warmed to room temperature, then stirred overnight. After TLC (eluent = 1 :1 EtOAc:Hex) confirmed that the reaction was complete, the reaction mixture was slowly added to ice water to quench the reaction, and stirred 20 minutes. The biphasic system was transferred to a separatory funnel for phase separation. The CH2CI2/ product solution was collected, simultaneously treated with Na2SO4 and Darco KB-B, filtered through a pad of celite and rinsed with CH2CI2. The filtrate was collected and vacuum stripped to a dark yellow oil, which solidified to a waxy yellow solid on standing. The solid was allowed to dry in a vacuum oven at 45C overnight. This afforded crude product as a yellow solid (17.9g of 90% pure as determined by HPLC). <n="12"/>The crude product (17.9g) was taken up in EtOH (90ml) and brought to reflux, which resulted in a clear yellow solution. The solution was allowed to slowly cool to room temperature and stir overnight. This gave a cream-colored slurry. The slurry was filtered onto a No.2 Whatman paper filter and rinsed with EtOH. The solid was then allowed to dry overnight in a vacuum oven at 45C. This afforded 14.6g (81.1 % yield) of a cream-colored solid.
  • 2
  • aluminum chloride (AlCl3) [ No CAS ]
  • [ 230615-51-7 ]
  • [ 75-34-3 ]
  • [ 230615-80-2 ]
YieldReaction ConditionsOperation in experiment
With acetyl chloride; A 1-(4-Acetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (253 mg, 1.0 mmol) and AcCl (0.68 mL, 10 mmol) were dissolved in DCE (3 mL) and treated with aluminum chloride (AlCl3) (667 mg, 5.0 mmol). The resulting yellow mixture was stirred for 30 minutes then poured over ice and saturated aqueous NaHCO3 solution. After stirring 20 minutes the mixture was extracted with CH2Cl2 (3*30 mL). The organic layer was dried through a cotton plug then concentrated to a orange-yellow oil (255 mg, 86%).
  • 3
  • [ 230615-52-8 ]
  • [ 407-25-0 ]
  • [ 230615-51-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃;Product distribution / selectivity; A suspension of 10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene hydrochloride (500 g) and MDC (8 l) was stirred at 0 to 5 C., and treated with triethylamine (621.4 g). To this solution, tri-fluoro acetic anhydride (645 g) was added at 0 to 5 C. over 30 to 40 minutes. The resulting solution was allowed to warm to room temperature, and stirred for 2 hours. The progress of the reaction was checked by HPLC. The reaction was quenched by addition of DM water (3.75 l) at 5 to 10 C., and stirred for 1.0 hour. The layers were separated, and the aqueous layer was extracted with MDC (1 l). The organic layer was washed with 1N HCl (3×3 l) and 10 percent aqueous sodium chloride solution (2 l). Concentration of the organic layer to 2 l provided a 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-yl)-2,2,2-trifluoro ethenone product, which was further processed as described below stage (HPLC purity 98.12 percent).
With pyridine; In dichloromethane; at 0℃; for 0.166667h; 10-Aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-triene hydrochloride salt (60 g) was stirred in methylene chloride (600 ml) at 25-30C, the mixture was cooled to 0C, and then treated with pyridine (61.68 g), followed by the addition of trifluoroacetic anhydride (TFAA) (81.39 g) over 10 minutes. Aqueous hydrochloric acid solution (600 ml) was added to the resulting mass followed by the separation of layers. The aqueous layer was extracted with methylene chloride (2 x 300 ml) and the combined organic layer was washed with aqueous hydrochloric acid solution (300 ml), water (2 x 600 ml) and saturated aqueous sodium bicarbonate solution (600 ml). The resulting solution was dried over sodium sulfate followed by concentration under vacuum at below 40C to afford a clear oil which was then crystallized to give 66 g of l-(10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone as white needles (Purity by HPLC: 99.33%).
With pyridine; In dichloromethane; A 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone 10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene hydrochloride salt (12.4 g, 63.9 mmol) was stirred in CH2Cl2 (200 mL). This was cooled (ice bath) and treated with pyridine (12.65 g, 160 mmol) followed by trifluoroacetic anhydride (TFAA) (16.8 g, 11.3 mL, 80 mmol) from an addition funnel over 10 minutes. After ~3 hours, the solution was poured into 0.5N aqueous HCl (200 mL) and the layers separated. The aqueous layer was extracted with CH2Cl2 (3*50 mL) and the combined organic layer was washed with 0.5N aqueous HCl (50 mL), H2O (2*50 mL) and saturated aqueous NaHCO3 solution (50 mL). This solution was dried through a cotton plug, then diluted with ~3% ethyl acetate and filtered through a 2 inch Silica pad eluted with ~3% ethyl acetate/CH2Cl2. Concentration afforded a clear oil which crystallized to give white needles (15.35 g, 60.2 mmol, 94%). (TLC 30% ethyl acetate/hexanes Rf 0.53). 1H NMR (400 MHz, CDCl3) delta7.18 (m, 4H), 4.29 (br d, J=12.6 Hz, 1H), 3.84 (br d, J=12.6 Hz, 1H), 3.51 (dd, J=12.6, 1.5 Hz, 1H), 3.21 (br s, 1H), 3.10 (br s, 1H), 3.10 (br d, J=12.6 Hz, 1H), 2.37 (m, 1H), 1.92 (d, J=10.8 Hz, 1H). GCMS m/e 255 (M+). M.p. 67-68 C.
  • 4
  • [ 230615-51-7 ]
  • [ 230615-53-9 ]
YieldReaction ConditionsOperation in experiment
94% With nitric acid; In trifluoroacetic acid; at 0℃; for 2.16667h; A solution of 1-(10-Aza-tricyclo[6.3.1.02l7]dodeca-2(7),3,5-trien- 10-yl)-2,2,2-trifluoro-ethanone (49.9g, 196 mmol) (4) (see O'Donnell et al., JOC, 2004 (69,7), 5756-59 and International Publication Nos. WO 04/063164 and WO 99/35131) and in trifluoroacetic acid (TFA) (100 mL) was cooled in an acetone/ice bath and treated drop-wise with fuming HNO3 over 10 minutes. The resultant reaction mixture was stirred for 1 hour as the ice bath temperature increased to 0C and then for an additional 1 hour. The ice bath was removed, excess NO2 was removed under a stream of nitrogen, and TFA was removed <n="84"/>under reduced pressure. The resultant residue was poured into 300 ml of ice water and extracted with 3 x 200 ml CH2CI2. The combined organic phases were washed with saturated NaCI (1 x 100 ml) and saturated NaHCO3. (1 x 100 ml). The organic phase was dried over MgSO4 and passed through a 200 g plug of silica gel (230-400 mesh) eluting with CH2CI2 (2000 ml). The resultant eluent was concentrated under reduce pressure to provide C17 as a pale yellow solid (55.4 g, 184 mmol, 94% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.1 (d, (d, J=4.6 Hz, 2 H) 3.7 (m, 1 H) 3.8 (m, 1 H) 4.1 (d, J=12.9 Hz, 1 H) 7.5 (t, J=8.5 Hz, 1 H) 8.1 (d, J=7.9 Hz, 1 H) 8.2 (dd, J=10.8, 2.1 Hz, 1 H) ppm.
78% With trifluorormethanesulfonic acid; nitric acid; In dichloromethane; B 1-(4-Nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (Based on the method described by Coon, C. L.; Blucher, W. G.; Hill, M. E. J. Org. Chem. 1973, 25, 4243.) To a solution of trifluoromethanesulfonic acid (2.4 ml, 13.7 mmol) in CH2Cl2 (10 ml) stirred at 0 C. was slowly added nitric acid (0.58 ml, 27.4 mmol) generating a white precipitate. After 10 minutes the resulting mixture was cooled to -78 C. and treated with <strong>[230615-51-7]1-(10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone</strong> (3.5 g, 13.7 mmol) in CH2Cl2 (15 ml) dropwise from an addition funnel over 5 minutes. The reaction was stirred at -78 C. for 30 minutes then warmed to 0 C. for 1 hour. The reaction mixture was poured into a vigorously stirred ice (100 g). The layers were separated and the aqueous layer extracted with CH2Cl2 (3*30 ml). The organic layer was combined and washed with H2O (3 *30 ml). The combined organic layer was washed with saturated aqueous NaHCO3 solution (20 mL) and H2O (20 mL) then dried through a cotton plug and concentrated to give an orange oil that solidified on standing (4.2 g). Chromatography yielded pure product as a crystalline solid (3.2 g, 78%). (TLC 30% ethyl acetate/hexanes Rf 0.23). 1H NMR (400 MHz, CDCl3) delta8.12 (br d, J=8.0 Hz, 1H), 8.08 (br s, 1H), 7.37 (br d, J=8.0 Hz, 1H), 4.38 (br d, J=12.6 Hz, 1H), 3.94 (br d, J=12.6 Hz, 1H), 3.59 (br d, J=12.6 Hz, 1H), 3.43-3.35 (m, 2H), 3.18 (br d, J=12.6 Hz, 1H), 2.48 (m, 1H), 2.07 (d, J=10.8 Hz, 1H). GCMS m/e 300 (M+).
YieldReaction ConditionsOperation in experiment
A 1-(10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone 10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-triene hydrochloride salt (12.4 g, 63.9 mmol) was stirred in CH2Cl2 (200 mL). This was cooled (ice bath) and treated with pyridine (12.65 g 160 mmol) followed by trifluoroacetic anhydride (TFAA) (16.8 g, 11.3 mL, 80 mmol) from an addition funnel over 10 minutes. After ~3 hours, the solution was poured into 0.5N aqueous HCl (200 mL) and the layers separated. The aqueous layer was extracted with CH2Cl2 (3*50 mL) and the combined organic layer was washed with 0.5N aqueous HCl (50 mL), H2O (2*50 mL) and saturated aqueous NaHCO3 solution (50 mL). This solution was dried through a cotton plug, then diluted with ~3% EtOAc and filtered through a 2 inch Silica pad eluted with ~3% EtOAc/CH2Cl2. Concentration afforded a clear oil which crystallized to give white needles (15.35 g, 60.2 mmol. 94%). (TLC 30% EtOAc/hexanes Rf 0.53). 1H NMR (400 MHz. CDCl3) delta 7.18 (m, 4H), 4.29 (br d. J=12.6 Hz, 1H), 3.84 (br d, J=12.6 Hz, 1 H), 3.51 (dd, J=12.6,1.5 Hz, 1H), 3.21 (br s, 1H), 3.10 (br s, 1H), 3.10 (br d, J=12.6 Hz, 1H), 2.37 (m, 1H), 1.92 (d, J=10.8 Hz, 1H). GCMS m/e 255 (M+) mp 67-68 C.
  • 6
  • aluminum chloride (AICl3) [ No CAS ]
  • [ 230615-51-7 ]
  • [ 75-34-3 ]
  • [ 230615-80-2 ]
YieldReaction ConditionsOperation in experiment
With acetyl chloride; A 1-(4-Acetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro Ethanone 1-(10-Aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (253 mg, 1.0 mmol) and AcCl (0.68 mL, 10 mmol) were dissolved in DCE (3 mL) and treated with aluminum chloride (AICl3) (667 mg, 5.0 mmol). The resulting yellow mixture was stirred for 30 minutes then poured over ice and saturated aqueous NaHCO3 solution. After stirring 20 minutes the mixture was extracted with CH2Cl2 (3*30 mL). The organic layer was dried through a cotton plug then concentrated to a orange-yellow oil (255 mg, 86%).
  • 7
  • [ 230615-51-7 ]
  • [ 230615-89-1 ]
YieldReaction ConditionsOperation in experiment
87% With chlorosulfonic acid; A 10-Trifluoroacetyl-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-triene-4-sulfonyl Chloride 1-(10-Aza-tricyclo(6.3.1.02.7]dodeca-2(7),3,5-trien-10-yl)-2.2,2-trifluoro-ethanone (530 mg. 2.1 mmol) was added to chlorosulfonic acid (2 mL, 30 mmol) and stirred for 5 minutes. The mixture was quenched with ice, extracted with EtOAc, dried (Na2SO4), filtered and concentrated to provide an oil (640 mg, 87%) (TLC 30% EtOAc/hexanes Rf 0.15).
87% With chlorosulfonic acid; A 10-Trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-4-sulfonyl Chloride 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (530 mg, 2.1 mmol) was added to chlorosulfonic acid (2 mL, 30 mmol) and stirred for 5 minutes. The mixture was quenched with ice, extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated to provide an oil (640 mg, 87%). (TLC 30% ethyl acetate/hexanes Rf 0.15).
  • 8
  • aluminum chloride (AlCl3) [ No CAS ]
  • [ 230615-51-7 ]
  • [ 230615-80-2 ]
YieldReaction ConditionsOperation in experiment
With acetyl chloride; A 1-(4-Acetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone 1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (253 mg, 1.0 mmol) and AcCl (0.68 mL, 10 mmol) were dissolved in DCE (3 mL) and treated with aluminum chloride (AlCl3) (667 mg, 5.0 mmol). The resulting yellow mixture was stirred for 30 minutes then poured over ice and saturated aqueous NaHCO3 solution. After stirring 20 minutes the mixture was extracted with CH2Cl2 (3*30 mL). The organic layer was dried through a cotton plug then concentrated to a orange-yellow oil (255 mg, 86%).
  • 9
  • [ 230615-51-7 ]
  • C13H11ClF3NO2S [ No CAS ]
  • 10
  • [ 230615-51-7 ]
  • 3-(trifluoroacetyl)-6,8-dinitro-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine [ No CAS ]
  • [ 230615-59-5 ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; nitric acid; In dichloromethane; at 0 - 15℃;Product distribution / selectivity; On the other hand, a 500 mL round bottom flask with thermometer, condenser, addition funnel and magnetic stirring was charged with CF3SO3H (25.9 g, 172.5 mmol), CH2Cl2 (110 mL) and cooled to 0-5 0C. At this temperature, fuming nitric acid (5.4 g, 86.25 mmol) was added slowly. To the resulting slurry at 0-5 0C, the solution obtained in the previous step was slowly added, maintaining the temperature < 15 0C. After the addition, the reaction mixture was stirred overnight. The complete dinitration was confirmed by GC. The crude reaction mixture was poured into water (60 mL) an ice (80 g) and stirred. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3 x 50 mL) . The mixture of the organic phases was washed with aqueous saturated NaHCO3, dried over Na2SO4 and volatiles evaporated under vacuum to obtain 11.9 g of a solid that was suspended and stirred for 2 hours in AcOEt (12 mL) and hexanes (24 mL) . The solid was filtered and washed with hexanes to <n="13"/>obtain the compound of formula (III), 9.1g with a purity of 88.9% by GC (9.8% of meta-dimtrocompound impurity) .
  • 11
  • [ 230615-51-7 ]
  • [ 75-36-5 ]
  • [ 230615-80-2 ]
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; ;