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[ CAS No. 32263-70-0 ]

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2D
Chemical Structure| 32263-70-0
Chemical Structure| 32263-70-0
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Product Details of [ 32263-70-0 ]

CAS No. :32263-70-0MDL No. :MFCD12024333
Formula : C17H16O2 Boiling Point : 433.4±34.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :252.31Pubchem ID :10682241
Synonyms :

Computed Properties of [ 32263-70-0 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 3.5 H-Bond Donor Count : 0
SP3 : 0.24 Rotatable Bond Count : 3

Safety of [ 32263-70-0 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 32263-70-0 ]

  • Upstream synthesis route of [ 32263-70-0 ]
  • Downstream synthetic route of [ 32263-70-0 ]

[ 32263-70-0 ] Synthesis Path-Upstream   1~4

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  • [ 3470-50-6 ]
  • [ 100-39-0 ]
  • [ 32263-70-0 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In acetone for 6.00 h; Reflux General procedure: 6-Hydroxy-1-tetralone (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane.
97% With potassium carbonate In acetone for 6.00 h; Reflux General procedure: 6-Hydroxy-1-tetralone (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane. 6-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one (6a) The title compound was prepared in a yield of 97percent: mp 100.9–102.1 °C (cyclohexane). 1H NMR (BrukerAvance III 600, CDCl3) δ 2.09 (p, J = 6.5 Hz, 2H), 2.56 – 2.61 (m, 2H), 2.90 (t, J = 6.1 Hz, 2H), 5.09 (s,2H), 6.77 (d, J = 2.2 Hz, 1H), 6.88 (dd, J = 8.7, 2.6 Hz, 1H), 7.30 – 7.36 (m, 1H), 7.36 – 7.43 (m, 4H),8.00 (d, J = 8.7 Hz, 1H); 13C NMR (Bruker Avance III 600, CDCl3) δ 23.29, 30.10, 38.85, 69.20, 113.53,113.58, 122.11, 126.64, 128.99, 129.67, 131.78, 135.20, 146.94, 162.30, 197.08; APCI-HRMS m/z: calcdfor C17H17O2 (MH+), 253.1223, found 253.1220.
94% With potassium carbonate In acetonitrile at 50℃; for 2.00 h; Step 1:
Preparation of 6-benzyloxytetralin-1-one
To a solution of 6-hydroxytetralin-l-one (100 g, 616.56 mmol, 1.00 eq) in acetonitrile (1000 mL) was added potassium carbonate (170.43 g, 1.23 mol, 2.00 eq) and benzyl bromide (126.54 g, 739.87 mmol, 88 mL, 1.20 eq).
The reaction mixture was stirred at 50° C. for 2 hours. TLC (petroleum ether:ethyl acetate=5:1) showed most of the starting material was consumed.
Water (1000 mL) was added to the mixture, the resulting mixture was extracted with ethyl acetate (600 mL*3).
The combined organic phase was washed with brine (800 mL), dried over sodium sulfate, filtered and concentrated in vacuum.
The residue was triturated with petroleum ether and ethyl acetate (303 mL, petroleum ether:ethyl acetate=100:1, V:V).
The mixture was filtered and the filter cake was washed with petroleum ether (50 mL*2), dried in vacuum to give 6-benzyloxytetralin-1-one (146 g, 578.65 mmol, 94percent yield) as a brown solid. 1H-NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 1H), 7.45-7.34 (m, 5H), 6.91 (dd, J=8.8, 2.4 Hz, 1H), 6.80 (d, J=2.4 Hz, 1H), 5.12 (s, 2H), 2.93 (t, J=6.0 Hz, 2H), 2.62 (t, J=6.4 Hz, 2H), 2.15-2.09 (m, 2H).
84% With potassium carbonate In acetonitrile at 15℃; for 3.00 h; Step 1:
6-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one 129a
To a mixture of 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one 101f (20.0 g, 123.31 mmol) and benzyl bromide (20 mL, 246.62 mmol) in MeCN (70 mL) was added K2CO3 (33.2 g, 240.21 mmol) at 15° C. and the resulting mixture was stirred for 3 hours.
The mixture was filtered, concentrated and the residue was purified by flash column chromatography eluted with 0-10percent EtOAc in petroleum ether to afford 129a (26 g, 84percent yield) as brown oil. 1H NMR (400 MHz, CDCl3) δ 8.06-7.98 (m, 1H), 7.46-7.32 (m, 5H), 6.90 (d, J=8.8 Hz, 1H), 6.80 (s, 1H), 5.16-5.08 (m, 2H), 2.93 (t, J=6.0 Hz, 2H), 2.62 (t, J=6.4 Hz, 2H), 2.17-2.06 (m, 2H).
80% With potassium carbonate In acetoneInert atmosphere of nitrogen; Heating; Reflux The mixture of 6-hydroxy-3,4-dihydro-2H-naphthalen-l-one (30.74 g, 0.1895 mol), benzyl bromide (27.0 mL, 0.227 mol) and potassium carbonate (39.3 g, 0.284 mol) in acetone (250 mL, 3.4 mol) was heated to reflux under an atmosphere of nitrogen for 3 hours. The mixture was cooled to 10 °C with an ice bath, filtered and washed with small amount of acetone. The filtrate was concentrated in rotavap. The resulting crystals were collected by filtration and washed with EtOAc-hexane then hexane to give a pale yellow solid product as the first crop. The mother liquid was concentrated in rotavapor and the residue was purified by chromatograph with EtOAc:hexane (0:100 to 20:80) to give the second crop of solid product (38.07g, 80percent). 1H NMR (CHLOROFORM-d) δ: 8.02 (d, J = 8.6 Hz, IH), 7.32 - 7.51 (m, 5H), 6.91 (dd, J = 8.8, 2.3 Hz, IH), 6.80 (s, IH), 5.13 (s, 2H), 2.93 (t, J = 6.1 Hz, 2H), 2.56 - 2.68 (m, 2H), 2.12 (quin, J = 6.3 Hz5 2H). MS (M+l): 253.0.
34.5g With potassium carbonate In acetone at 40℃; for 3.50 h; To a solution of 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one (CAS registry number: 3470-50-6) (24.3 g) inacetone (160 mL), benzyl bromide (29.4 mL) and potassium carbonate (31.1 g) were added at room temperature andthe mixture was stirred at 40°C for 3.5 hours. After insoluble matters were filtered off, the mixture was concentrated andwashed with a mixed solvent of tert-butyl methyl ether (MTBE)-hexane (1 : 4) to give the title compound (34.5 g) havingthe following physical property.TLC: Rf 0.38 (hexane : ethyl acetate = 3 : 1).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
[3] Patent: US2018/155322, 2018, A1. Location in patent: Paragraph 1502; 1503
[4] European Journal of Organic Chemistry, 2003, # 15, p. 2799 - 2812
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 144 - 148
[6] Patent: US2017/129855, 2017, A1. Location in patent: Paragraph 0243
[7] Patent: WO2010/51031, 2010, A1. Location in patent: Page/Page column 64-65
[8] Patent: US6359138, 2002, B1. Location in patent: Page column 34
[9] ChemMedChem, 2010, vol. 5, # 9, p. 1577 - 1593
[10] Journal of Medicinal Chemistry, 1996, vol. 39, # 26, p. 5035 - 5046
[11] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 99 - 102
[12] Patent: EP1577288, 2005, A1. Location in patent: Page/Page column 165
[13] Patent: WO2006/64757, 2006, A1. Location in patent: Page/Page column 80
[14] Patent: EP1760071, 2007, A1. Location in patent: Page/Page column 49
[15] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729
[16] Patent: US2014/100195, 2014, A1. Location in patent: Page/Page column
[17] Patent: EP3228615, 2017, A1. Location in patent: Paragraph 0104
[18] Patent: EP1661881, 2006, A2. Location in patent: Page/Page column 122-123
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  • [ 3470-50-6 ]
  • [ 100-44-7 ]
  • [ 32263-70-0 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 517-527
[2] Archiv der Pharmazie (Weinheim, Germany), 1994, vol. 327, # 2, p. 99 - 104
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  • [ 3470-50-6 ]
  • [ 100-39-0 ]
  • [ 32263-70-0 ]
Reference: [1] Patent: EP1826197, 2007, A1
  • 4
  • [ 1078-19-9 ]
  • [ 32263-70-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 99 - 102
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
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