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[ CAS No. 68449-30-9 ] {[proInfo.proName]}

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Chemical Structure| 68449-30-9
Chemical Structure| 68449-30-9
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Product Details of [ 68449-30-9 ]

CAS No. :68449-30-9 MDL No. :MFCD02179288
Formula : C10H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :DMXOUYZZHVHEQR-UHFFFAOYSA-N
M.W : 225.08 Pubchem ID :10889572
Synonyms :

Calculated chemistry of [ 68449-30-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.0
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 3.18
Log Po/w (WLOGP) : 2.97
Log Po/w (MLOGP) : 2.71
Log Po/w (SILICOS-IT) : 3.68
Consensus Log Po/w : 2.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0554 mg/ml ; 0.000246 mol/l
Class : Soluble
Log S (Ali) : -3.21
Solubility : 0.139 mg/ml ; 0.000617 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.25
Solubility : 0.0125 mg/ml ; 0.0000557 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 68449-30-9 ]

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 [ 68449-30-9 ]

* 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.

  • Upstream synthesis route of [ 68449-30-9 ]
  • Downstream synthetic route of [ 68449-30-9 ]

[ 68449-30-9 ] Synthesis Path-Upstream   1~17

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Reference: [1] Patent: US2003/225281, 2003, A1,
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YieldReaction ConditionsOperation in experiment
51% at 80℃; Example 1; Preparation of 7-Bromo-l-tetralone; 7-bromo-1-tetralone was prepared according to the procedure described in Cornelius, L. A. M.; Combs, D. W. Synthetic Communications 1994,24, 2777-2788. The above isomers were separated using silica gel flash chromatography (Biotage Flash 75, elution solvent 20/1 hexanes: MTBE) to yield 5-bromo-1-tetralone (11.59 g, 51percent) and 7-bromo-1-tetralone (9.45 g, 42percent).
42% at 75 - 80℃; for 0.55 h; A 500 mL three-necked flask fitted with an addition funnel, reflux condenser and thermometer was charged with aluminum chloride (33.34 g, 250 mmol) and heated to 75-80 °C. 1- Tetralone (14.6 g, 13.3 ML, 100 mmol) was added dropwise over 10 min. The resulting brown slurry was stirred for 3 min before dropwise addition of bromine (19.21 g, 6.15 ml, 120 mmol) over 15 min. The mixture was stirred for 5 min and then poured into a mixture of ice (300 g) and 12N HC1 (40 mL). The mixture was stirred until the aluminum chloride was dissolved and then diluted with water (200 mL). The mixture was extracted with diethyl ether (3 X 300 mL) and the combined organics were washed with water (2 X 300 mL), dried (sodium sulfate), filtered and evaporated in vacuo to give a dark brown mixture of 5-and 7- BROMO-1-TETRALONE. The isomers were separated using silica gel flash chromatography (Biotage Flash 75, elution solvent 20/1 hexanes: MTBE) to yield 5-BROMO-1-TETRALONE (11.59 g, 51percent) and 7- BROMO-1-TETRALONE (9.45 g, 42percent).
42%
Stage #1: at 75 - 80℃; for 0.216667 h;
Stage #2: for 0.333333 h;
A 500 mL three-necked flask fitted with an addition funnel, reflux condenser and thermometer was charged with aluminum chloride (33.-34 g, 250 mmol) and heated to 75-80 °C. 1- Tetralone (14.6 g, 13.3 mL, 100 mmol) was added dropwise over 10 MIN. THE resulting brown slurry was stirred for 3 min before dropwise addition of bromine (19.21 g, 6.15 ml, 120 mmol) over 15 min. The mixture was stirred for 5 min and then poured into a mixture of ice (300 g) and 12N HC1 (40 mL). The mixture was stirred until the aluminum chloride was dissolved and then diluted with water (200 mL). The mixture was extracted with diethyl ether (3 X 300 mL) and the combined organics were washed with water (2 X 300 mL), dried (sodium sulfate), filtered and evaporated in vacuo to give a dark brown mixture of 5-and 7- BROMO-1-TETRALONE. The isomers were separated using silica gel flash chromatography (Biotage Flash 75, elution solvent 20/1 hexanes: MTBE) to yield 5-BROMO-1-TETRALONE (11.59 g, 51percent) and 7- BROMO-1-TETRALONE (9.45 g, 42percent). [Note 1. Procedure: Cornelius, L. A. M.; Combs, D. W. Synthetic Communications 1994,24, 2777-2788].
Reference: [1] Patent: WO2005/95326, 2005, A2, . Location in patent: Page/Page column 110-111
[2] Patent: WO2004/94384, 2004, A2, . Location in patent: Page 63-64
[3] Patent: WO2004/94413, 2004, A1, . Location in patent: Page 63-64
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 29 - 35
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 16, p. 4405 - 4409
[6] Synthetic Communications, 1994, vol. 24, # 19, p. 2777 - 2788
[7] Gazzetta Chimica Italiana, 1988, vol. 118, # 5, p. 369 - 374
[8] Patent: US5753655, 1998, A,
[9] Patent: US2004/6229, 2004, A1, . Location in patent: Page/Page column 13-14
[10] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1381 - 1392
[11] Patent: US2003/225281, 2003, A1, . Location in patent: Page 12
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YieldReaction ConditionsOperation in experiment
44%
Stage #1: at 0 - 90℃; for 0.916667 h;
Stage #2: at 90℃; for 1 h;
Example III
Synthesis of Tetrahydronaphthalene Derivatives
5-Bromo-1-tetralone. (Cornelius, L. A. H.; Combs, D. W. Synthetic Communications 1994, 24(19), 2777-2788) Into a round bottom flask kept at 0° C., AlCl3 (19.6 g, 146.8 mmol) was added and the reaction system was put under nitrogen. 8 mL of tetralone (8.62 g, 58.9 mmol) were added during a 10-minute period, at which point, the reaction mixture was heated in an oil bath at 90° C. for about 45 minutes before adding 3.6 mL of Br2 (11.2 g, 70.1 mmol).
The reaction mixture was stirred at 90° C. for an hour before 30 mL of ice-water and 20 mL of NaHCO3 were added.
The product was extracted twice from the aqueous phase with Et2O and, the resultant organic phase was washed once with NaHCO3, once with brine and dried under Na2SO4.
The crude reaction mixture was purified by flash chromatography (2.5percent EtOAc/97.5percent hex) which afforded 5.87 g (26.1 mmol) of the product in a 44percent yield.
1H NMR (300 MHz, CDCl3, δ): 8.01 (dd, J=7.8, 1.3, Ar, 1H), 7.73 (dd, J=7.9, 1.3, Ar, 1H), 7.18 (tt, J=7.9, 0.6, Ar, 1H), 3.01 (t, J=6.2, C2, 2H), 2.64 (dd, J=6.7, 5.6, C2, 2H), 2.15 (td, J=13.0, 6.5, C2, 2H).
13C NMR (75 MHz, CDCl3): δ 197.5, 143.4, 137.3, 134.9, 127.7, 126.5, 124.8, 38.2, 30.0, 22.3.
Dept 135 NMR (75 MHz, CDCl3): δ 137.3 (H), 127.7 (H), 126.5 (H), 38.2 (H2), 30.0 (H2), 22.3 (CH2).
EIMS: m/z (percent rel. intensity) 226 (M++2, 93), 224 (M+, 93), 211 (25), 209 (25), 198(100), 196 (100), 170 (50), 168 (50), 145 (25), 115 (45), 89 (60), 63 (28).
27%
Stage #1: at 70℃;
Stage #2: at 20 - 80℃; for 0.416667 h;
Stage #3: at 0℃;
To prepare this compound, 1-tetralone (10.2 g, 70 mmol) was added dropwise to a slurry of aluminum trichloride (23.3 g, 175 mmol) heated to 70 °C in a 3-neck flask with an outlet tube connected to a 2 M sodium carbonate solution. The slurry was stirred with a spatula. After the addition of 1-tetralone, the slurry was removed from heat and allowed to cool to room temperature. Bromine (12.3 g, 77 mmol) was added dropwise over 15 minutes. After that addition was complete, the slurry was heated at 80 °C for 10 minutes, then it was poured into a mixture of 200 grams of ice and 25 mL concentrated HC1. The 3-neck flask was rinsed with water and that rinse water was also added to the ice and slurry solution. That solution was extracted twice with ether (200 mL each) and those two extracts were combined. The combined ether extract was washed sequentially with water (50 mL), saturated sodium bicarbonate (25 mL), and brine (100 mL), and then was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil. The oil was subjected to flash chromatography (12percent THF/hexanes), and the resultant product was recrystallized from hexanes to afford 4.4 g (27percent) of 5-bromo-3,4-dihydro-2No.-naphthalen-l-one. XH NMR (500 MHz, CDC13) 5 8.03 (dd, J = 7.7, 1.2, 1H), 7.75 (dd, J = 7.7,1.2, 1H), 7.20 (t, J = 7.8,1H), 3.03 (t, J = 6.2, 2H), 2.66 (t, J = 6.5, 2H), 2.15-2.20 (m, 2H).
Reference: [1] Patent: US2009/76076, 2009, A1, . Location in patent: Page/Page column 20
[2] Journal of the American Chemical Society, 2018, vol. 140, # 12, p. 4317 - 4326
[3] Patent: WO2006/23158, 2006, A2, . Location in patent: Page/Page column 54
[4] Patent: US2011/65699, 2011, A1, . Location in patent: Page/Page column 10-11
[5] Patent: WO2015/179366, 2015, A1, . Location in patent: Paragraph 00172
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YieldReaction ConditionsOperation in experiment
28.3%
Stage #1: Under N2
Stage #2: at 80℃; for 0.0833333 h;
Anhydrous AlCl3 (66.67 g, 0.50 mol, 99.99percent) under N2 was stirred vigorously as 1-tetralone (29.83 g, 0.20 mol) was added dropwise over 7 min. The evolved HCl gas was scrubbed through 5 N NaOH. The resulting mixture was a dark brown oil that exothermed to 75° C. When the temperature had cooled to 50° C., Br2 was added dropwise over 15 min. The mixture, which had cooled further to 40° C., was heated to 80° C. for 5 min, then poured into a mixture of ice (600 g) and 12 N HCl (80 mL). All the ice melted, leaving a cool dark mixture which was diluted with H2O (200 mL) and extracted with CH2Cl2 (200 mL, 100 mL). The combined extracts were dried with MgSO4 and concentrated in vacuo (30-60° C.) to a dark brown oil (45.6 g; theory=45.02 g).[0085] Chromatography over silica gel 60 with 8:1 heptane:THF did not prove effective, but two passes through the Biotage radially pressured silica gel cartridges using 9:1 heptane:MTBE as eluent produced acceptably pure fractions. [0086] 5-Bromo-3,4-dihydro-1(2H)-naphthalenone was isolated as an orange oil (12.27 g, 28.3percent). HPLC showed an apparent wide divergence in absorbances at 230 nm for the two regioisomers, and was therefore not reliable for a potency check. TLC on silica gel (4:1 heptane:MTBE) confirmed modest contamination with 7-bromo-3,4-dihydro-1(2H)-naphthalenone. [0087] 7-Bromo-3,4-dihydro-1(2H)-naphthalenone was isolated as a yellowish-white solid (15.48 g, 35.8percent); mp 69.5-75° C. (lit 74-75° C.). 1H NMR (CDCl3) corresponded to the literature description, plus a trace of heptane and an undefined by-product. TLC showed it to be cleaner than 5-bromo-3,4-dihydro-1(2H)-naphthalenone. [0088] A third fraction of orange oil (9.06 g, 20.9percent) was isolated. TLC showed it to be a nearly 1:1 ratio of 5-bromo-3,4-dihydro-1(2H)-naphthalenone, and 7-bromo-3,4-dihydro-1(2H)-naphthalenone.
Reference: [1] Patent: US2003/232833, 2003, A1, . Location in patent: Page 12
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6640 - 6658
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Reference: [1] Patent: US5086074, 1992, A,
[2] Patent: US5128362, 1992, A,
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6640 - 6658
[2] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6640 - 6658
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6640 - 6658
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Reference: [1] Patent: US2003/225281, 2003, A1,
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