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[ CAS No. 1208395-99-6 ]

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2D
Chemical Structure| 1208395-99-6
Chemical Structure| 1208395-99-6
Structure of 1208395-99-6 *Storage: {[proInfo.prStorage]}

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Related Doc. of [ 1208395-99-6 ]

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Product Details of [ 1208395-99-6 ]

CAS No. :1208395-99-6MDL No. :MFCD28124082
Formula :C16H12O3Boiling Point :-
Linear Structure Formula :-InChI Key :C(C1C=CC(=CC=1)O)(C1C=CC(=CC=1)OCC#C)=O
M.W :252.26Pubchem ID :46229706
Synonyms :

Computed Properties of [ 1208395-99-6 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1208395-99-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1208395-99-6 ]

  • Downstream synthetic route of [ 1208395-99-6 ]

[ 1208395-99-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1208395-99-6 ]
  • N-(2-(2-(2-(2-(4-((4-(4-(3-(2-(2-methoxy-5-((5,6,7-trimethoxy-4-oxochroman-3-yl)methyl)phenoxy)acetamido)propoxy)benzoyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]
  • 2
  • [ 58885-58-8 ]
  • [ 1208395-99-6 ]
  • tert-butyl (3-(4-(4-(prop-2-yn-1-yloxy)benzoyl)phenoxy)propyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 3h; [0173] tert-butyl (3-(4-(4-(prop-2-yn-l- yloxy)benzoyl)phenoxy)propyl)carbamate (B in FIG. 5). To a THF solution (2 mL) of N-Boc 3-aminopropanol (117 mg, 0.76 mmol) were added the propargylated benzophenone (140 mg, 0.56 mmol), PPh3 (150 mg, 0.76 mmol), and DIAD (130 mu, 0.56 mmol) at room temperature. After stirring for 3 hours at room temperature, the reaction mixture was diluted with ethyl acetate and the combined organic phase was washed with water and brine, dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (Ethyl acetate / n-hexane = 1 : 3) to afford the dialkylated dihydroxybenzophenone (B) (160 mg, 70%). 1H-NMR (600 MHz, CDCls) delta 7.77 (dd, 4H, J= 9.0 and 5.0 Hz), 7.03 (d, 2H, J= 9.0 Hz), 6.93 (d, 2H, J= 9.0 Hz), 4.82 (bs, 1H), 4.75 (d, 2H, J= 1.2Hz), 4.09 (t , 2H, J= 6.0 Hz), 3.33 (m, 2H), 2.56 (t, 1H, J= 2.4 Hz), 2.01 (m, 1H), 1.42 (s, 9H), 1.25 (m, 1H); 13C-NMR (150 MHz, CDC13) delta 194.3, 162.1, 160.6, 156.0, 132.2, 132.1, 131.5, 130.6, 114.3, 113.9, 77.8, 76.1, 65.9, 55.8, 37.8, 29.5, 28.4, 14.2; LRMS (ESI) m/z 432 (M+H).
70% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 3h; To a THF solution (2 mL) of N-Boc-3-aminopropanol (117 mg, 0.76 mmol) were added thepropargylated benzophenone (6') (140mg, 0.56 mmol), PPh3 (150 mg, 0.76 mmol), and DIAD (130 muL, 0.56mmol) at room temperature. After stirring for 3 h at room temperature, thereaction mixture was diluted with ethyl acetate and the combined organic phasewas washed with water and brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (ethyl acetate / n-hexane = 1 : 3) to afford thedialkylated dihydroxybenzophenone (7)(160 mg, 70%). 1H-NMR (600 MHz, CDCl3) delta 7.77 (dd, 4H, J = 9.0 and 5.0 Hz), 7.03 (d, 2H, J = 9.0 Hz), 6.93 (d, 2H, J = 9.0 Hz), 4.82 (bs, 1H), 4.75 (d, 2H,J = 1.2 Hz), 4.09 (t , 2H, J = 6.0 Hz), 3.33 (m, 2H), 2.56 (t, 1H, J = 2.4 Hz), 2.01 (m, 1H), 1.42 (s, 9H),1.25 (m, 1H); 13C-NMR (150 MHz, CDCl3) delta 194.3, 162.1,160.6, 156.0, 132.2, 132.1, 131.5, 130.6, 114.3, 113.9, 77.8, 76.1, 65.9, 55.8,37.8, 29.5, 28.4, 14.2; HRMS(ESI): mass calcd for C24H27NO5 [M + H] +, 410.1889; found, 410.1956.
  • 4
  • [ 1208395-99-6 ]
  • Boc-protected benzophenone-biotin [ No CAS ]
  • 5
  • [ 1208395-99-6 ]
  • C59H71N7O16S [ No CAS ]
  • 6
  • [ 1208395-99-6 ]
  • [ 1314092-54-0 ]
  • [ 1314092-55-1 ]
YieldReaction ConditionsOperation in experiment
96% fJG-199 . A round-bottomed flask was charged sequentially with K2C03 (44 mg, 0.32 mmol, 2 equiv), anhydrous dimethyl formamide (1 mL), and 4,4'-dihydroxybenzophenone derivative JG-195 B (40 mg, 0.15 mmol, 1 equiv) and the contents were stirred under an atmosphere of argon for 20 min. (+)-S-glycidyl nosylate (83 mg, 0.32 mmol, 2 equiv) was added via syringe dissolved in anhydrous dimethyl formamide (0.3 mL) and the mixture was allowed to react at room temperature for 8 h. Then, the solution was quenched with deionized water (~ 0.5 mL) and the mixture was extracted with ethyl acetate (3 x 2 mL). The organic layer was washed with deionized water (2 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5% ethyl acetate in dichloromethane) to provide JG-199 (47 mg, 96%) as a white solid.H NMR (400 MHz, DMSO-rf6): delta 7.70 (dd, J = 8.8, 2.0, 4H), 7.1 1 (t, J= 8.0, 4H),4.91 (d, J= 2.4, 2H), 4.44 (dd, J= 11.2, 2.4, 1H), 3.94 (dd, J= 11.6, 6.4, 1H), 3.63 (t, J= 2.0, 1H), 3.37 (m, 1H), 2.86 (t, J= 4.8, 1H), 2.73 (dd, J= 5.2, 2.8, 1H).13C NMR (100 MHz, DMSO-i 6): delta 193.7, 162.2, 161.0, 132.5, 132.3, 131.3, 130.8,1 16.2, 1 14.9, 79.4, 79.3, 69.9, 56.3, 55.5, 50.1 ,44.4.HRMS (ESI) (m/z): naTLC (5% methanol in dichloromethane), Rf. 0.73 (UV, p-anisaldehyde).
  • 7
  • [ 1208395-99-6 ]
  • [ 109-64-8 ]
  • [ 1314090-65-7 ]
YieldReaction ConditionsOperation in experiment
88% (JG-200). To a stirred solution of 4,4'-dihydroxybenzophenone derivative JG-195 B (10 mg, 0.04 mmol, 1 equiv) in anhydrous dimethyl formamide (0.4 mL) at rt was added K2C03 (11 mg, 0.08 mmol, 2 equiv) and the mixture was stirred for 20 min under argon atmosphere. 1,3-Dibromopropane (40 mu, 0.39 mmol, 10 equiv) was added and the mixture was stirred for 2 h at rt. Deionized water (0.2 mL) was added and the mixture was extracted with ethyl acetate (3 xl mL). The organic layer was washed with deionized water (1 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5% ethyl acetate in dichloromethane) to provide JG- 200 (13 mg, 88%) as a colourless oil.'H NMR HOO 10.8,8.8, 4H), 4.91 (d, J= 2.4, 2H), 4.19 (t, J= 6.0, 2H), 3.68 (t, J= 6.4, 2H), 3.63 (t, J= 2.0, 1H), 2.28 (q, 2H).1 C NMR (100 MHz, DMSO- 6): delta 193.7, 162.3, 161.0, 132.5, 132.3, 131.3, 130.7,115.2, 114.9, 79.4, 79.3, 66.3, 56.3, 32.3, 31.7. HRMS (ESI) (m/z): naTLC (5% methanol in dichloromethane), Rf. 0.79 (UV, -anisaldehyde).
  • 8
  • [ 1208395-99-6 ]
  • [ 139115-91-6 ]
  • [ 1246843-41-3 ]
  • 9
  • [ 611-99-4 ]
  • [ 106-96-7 ]
  • [ 1208395-99-6 ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate; In acetone; at 0 - 50℃; for 3h; To a solution of 4,4'-dihydroxybenzophone (500 mg,2.33 mmol) in acetone (5.0 ml) at 0C, K2CO3 (161 mg, 1.17 mmol) andpropargyl bromide (0.11 ml, 1.16 mmol) were added. The reaction mixture wasstirred at 50 C for 3 h, cooled to room temperature, and quenched with H2O (10 mL). The mixture was extracted threetimes with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, filtered, andconcentrated. The residue was purified via Biotage (ethyl acetate / n-hexane = 1 : 2 Snap Ultra25g column). The desired fractions were collected and concentrated togive propargylatedbenzophenone (6') (240 mg, 82% BRSM). 1H-NMR (600 MHz, CD3OD)delta 7.73 (d, 2H, J = 8.4 Hz), 7.67 (d,2H, J = 8.4 Hz), 7.09 (d, 2H, J = 9.0 Hz), 6.87 (d, 2H, J = 9.0 Hz), 4.82 (s, 2H), 3.00 (t , 1H,J = 2.4 Hz); 13C-NMR (150MHz, CD3OD) delta 195.4, 162.0, 161.0, 132.3, 131.6, 131.1, 128.9,114.7, 114.7, 77.8, 75.9, 55.3; HRMS(ESI): mass calcd for C16H15O3 [M + H] +, 253.0786; found, 253.0872.
46% (JG-195 B). To a stirred solution of 4,4'-dihydroxybenzophenone (250 mg, 1.16 mmol, 1 equiv) in anhydrous dimethyl formamide (2 mL) at rt was added K2C03 (242 mg, 1.75 mmol, 1.5 equiv) and the mixture was stirred for 20 min under argon atmosphere. Propargyl bromide (156 mu, 1.75 mmol, 1.5 equiv) was added and the mixture was stirred for 14.5 h at rt. Deionized water (0.5 mL) was added and the mixture was extracted with ethyl acetate (3 x2 mL). The organic layer was washed with deionized water (2 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 5% ethyl acetate in dichloromethane) to provide JG-195 B (135 mg, 46%) as a white solid.H NMR (400 MHz, DMSO- 6): delta 10.32 (s, 1H), 7.68 (d, J= 8.8, 2H), 7.62 (d, J =8.8, 2H), 7.1 1 (d, J = 8.8, 2H), 6.88 (d, J= 8.4, 2H), 4.91 (d, J= 2.4, 2H), 3.63 (t, J= 2.0, 1H). C NMR (100 MHz, DMSO- ): delta 193.7, 162.2, 160.8, 132.8, 132.1, 131.6, 129.0,115.7, 1 15.1 , 79.4, 79.3, 56.3.HRMS (ESI) irnlz): naTLC (5% methanol in dichloromethane), Rf: 0.48 (UV, /7-anisaldehyde).
33% With potassium carbonate; In acetone; for 5h;Reflux; [0172] (4-hydroxyphenyl)(4-(prop-2-yn-l-yloxy)phenyl)methanone. To an acetone solution (5.0 mL) of 4,4'-dihydroxybenzophenone (512 mg, 2.4 mmol) were added propargyl bromide (0.21 mL, 2.4 mmol) and K2CC"3 (495 mg, 3.6 mmol). After refluxing for 5 hours, the reaction mixture was diluted with ethyl acetate and the combined organic phase was washed with water and brine, dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (Ethyl acetate / n-hexane = 1 : 2) to afford the propargylated benzophenone (197 mg, 33%).
  • 10
  • [ 1208395-99-6 ]
  • [ 74808-10-9 ]
  • [ 1208396-02-4 ]
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