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Product Details of [ 80793-25-5 ]

CAS No. :80793-25-5 MDL No. :MFCD07772913
Formula : C9H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :RXZJWVPNFPPSEM-UHFFFAOYSA-N
M.W : 213.07 Pubchem ID :11481288
Synonyms :

Calculated chemistry of [ 80793-25-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.92
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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 2.58
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.32
Consensus Log Po/w : 2.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.321 mg/ml ; 0.00151 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 1.05 mg/ml ; 0.00493 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0206 mg/ml ; 0.0000968 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 80793-25-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 80793-25-5 ]

* 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 [ 80793-25-5 ]
  • Downstream synthetic route of [ 80793-25-5 ]

[ 80793-25-5 ] Synthesis Path-Upstream   1~18

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Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3920 - 3924
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YieldReaction ConditionsOperation in experiment
96% With Dess-Martin periodane In dichloromethane at 20℃; for 2 h; Example A.4: Synthesis of 3-(4-bromophenyl)propanal (10*) Alcohol 4* (4.71g, 21.8mmol) was dissolved in DCM, treated with Dess-Martin periodinane (9.71g, 20.9mmol) and stirred at rt for 2h. The mixture was quenchedwith 2M NaOH, the phases were separated the aqueous layer extracted with DCM. The combined organic phases were dried on Mg504, filtered and evaporated in vacuo. The crude was purified by flash chromatography on silica gel using a gradient of DCM in cHex to yield the desired product 10* (4.46g, 96percent) as a colourless liquid.1H NMR (400MHz, CDCI3) 6 9.81 (5, 1H), 7.41 (d, 2H), 7.07 (d, 2H), 2.91 (t, 2H),2.79-2.74 (m, 2H).MS (ES) C9H9BrO requires: 211/213, (Mi-H) not found, 100percent.
86%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 3 h;
Oxalyl chloride (0.599 mL, 6.973 mmol) was dissolved in DCM (15 mL), and DMSO (0.99 mL, 13.94 mmol)dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirred for 15 minutes, and 3-(4-bromophenyl)propan-1-ol (1.0 g, 4.64 mmol) dissolved in DCM (10 mL) was slowly added thereto at -78°C. The mixture was stirredfor 30 minutes, and TEA (1.96 mL) was slowly added thereto at -78°C. The temperature was slowly increased to roomtemperature, and the reaction solution was stirred for 3 hours. After termination of the reaction, the reaction solutionwas diluted with water and extracted with DCM. The organic layer was dried with anhydrous magnesiumsulfate andpurified by column chromatography (eluent, EtOAc/Hex = 1/5) to obtain the title compound (0.859 g, 86percent).NMR: 1H-NMR (CDCl3) δ 9.81(1H, s), 7.40 (2H, d), 7.07(2H, d), 2.91(2H, m), 2.77(2H, t)
76.9% With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 4 h; 3-(4-Bromophenyl) propan-1-ol (4 g, 18.5 mmol, 1.0 equiv) was dissolved into dichloromethane (60 mL) and cooled to 0°C. PCC (5.21 g, 24.1 mmol, 1.5 equiv) was added in portions and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite bed and the filtrate was concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (10-20 percent diethyl ether/n-pentane) to afford the desired product 5.21a (3.05 g, 76.9 percent yield). 1H NMR (400 MHz, CDCI3) 69.83 (s, 1H), 7.43 (d, J = 8.3 Hz, 2H), 7.10 (d, J 8.2 Hz, 2H), 2.94 (t, J 7.3 Hz, 2H), 2.79 (t, J 7.4 Hz, 2H).
58.5% With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 0 - 20℃; To a 0° C. mixture of 26A (7 g, 32.5 mmol) and NaHCO3 (3.28 g, 39.1 mmol) in DCM (200 mL) was added Dess-Martin periodinane (16.56 g, 39.1 mmol) and the reaction was allowed to slowly warm to rt overnight. The reaction was diluted with sat. aq. NaHCO3 (150 mL) and extracted with DCM (50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (SiO2; 80 g; A=Hex, B=EtOAc; 20 min gradient from 0percent B to 40percent B; flow rate=60 mL/min) to afford the title compound (4.06 g, 19.1 mmol, 58.5percent yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 9.82 (t, J=1.2 Hz, 1H), 7.48-7.37 (m, 2H), 7.19-6.97 (m, 2H), 3.02-2.88 (m, 2H), 2.83-2.70 (m, 2H).

Reference: [1] Patent: WO2015/181272, 2015, A1, . Location in patent: Page/Page column 30
[2] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0120
[3] Patent: WO2015/66413, 2015, A1, . Location in patent: Page/Page column 176; 177
[4] Patent: US2017/253554, 2017, A1, . Location in patent: Paragraph 0425; 0426
[5] Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877
[6] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 555 - 558
[7] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6187 - 6190
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YieldReaction ConditionsOperation in experiment
69% at 40℃; for 8 h; Inert atmosphere Under a nitrogen atmosphere, compound (T-19) (50.0 g), allyl alcohol (24.2 mL)), palladium acetate (0.794 g), sodium hydrogencarbonate (44.5 g) and tetrabuthyl ammonium chloride (TBAC) (54.0 g) were put in a reaction vessel, and the resulting mixture was stirred at 40°C for 8 hours. The resulting reaction mixture was poured into water, and the resulting aqueous layer was subjected to extraction with ethyl acetate. Then, organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to give compound (T-20) (26.1 g; 69percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2074 - 2077
[2] Patent: EP2957554, 2015, A1, . Location in patent: Paragraph 0162
[3] Patent: WO2008/51405, 2008, A1, . Location in patent: Page/Page column 70
[4] Chemical Communications, 2016, vol. 52, # 17, p. 3532 - 3535
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YieldReaction ConditionsOperation in experiment
70% With choline In tetrahydrofuran; water; toluene at 75℃; for 5 h; Weighing 2.632g choline reagent, 15mLH 2 O, 2 ml tetrahydrofuran, 8.4 ml toluene in 100 ml in three-mouth bottle, heating to 75 °C. The 25.08g the bromine animal pen chlorine and 4.4g acetaldehyde dissolved in 12 ml of tetrahydrofuran, is dripped slowly into the reaction flask. To continue this temperature reaction 5h, TLC showed reaction is ended. Reaction liquid cooling to room temperature, add 50 ml water, ethyl acetate extraction three times, combining oil layer, dry anhydrous sodium sulfate, concentrated dry solvent, column chromatography to obtain 18.24g bombycinous A transparent oily liquid compound. MSm/z: 212 (M +), yield: 70percent
70% With choline chloride In tetrahydrofuran; water; toluene at 75℃; for 5 h; Weigh 2.632 g of choline reagent (choline reagent), 15 mL of H20, 2 mL of tetrahydrofuran, 8.4 mL of toluene in a 100 mL three-necked flask and heated to 75 ° C. 25.08 g of p-bromobenzyl chloride and 4.4 g of acetaldehyde were dissolved in 12 mL of tetrahydrofuran and slowly added dropwise to the reaction flask. At this temperature for 5 h, TLC showed the reaction to end.The reaction solution was cooled to room temperature, extracted with 50 mL of water and 100 mL of ethyl acetate. The combined wells were dried over anhydrous sodium sulfate and concentrated to dryness. Column chromatography gave 18.24 g of a pale yellow transparent oily liquid compound.yield: 70percent
Reference: [1] Patent: CN104513129, 2016, B, . Location in patent: Paragraph 0094; 0095; 0096; 0097
[2] Patent: CN104513140, 2016, B, . Location in patent: Paragraph 0036-0039
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Reference: [1] Synlett, 2006, # 19, p. 3343 - 3345
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Reference: [1] Chinese Journal of Catalysis, 2017, vol. 38, # 4, p. 691 - 698
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YieldReaction ConditionsOperation in experiment
55% With PdCl2/PVP-K30; sodium acetate In N,N-dimethyl-formamide at 85℃; for 3 h; Inert atmosphere The reaction was carried out in a 50 cm3 Schlenk tube. The solid substrates, NaOAc (2 mmol), and the Pd catalysts (1 105 mol) were weighed and placed in the Schlenk tube under a N2 atmosphere. Next, olefin, aryl dihalides (1 mmol), and 5 cm3 of DMF were added with a pipette. The Schlenk tube was closed with a rubber plug, and the reaction mixture was stirred at 85 °C. After the given reaction time, the reactor was cooled down, and the organic products were separated by extraction with diethyl ether (three times with 7, 7, and 7 cm3). For better phase separation, 5 cm3 of water was added, and the products were and GC-MS analyzed (Hewlett Packard 8454A) with mesitylene (0.076 cm3) as the internal standard.
Reference: [1] Tetrahedron, 2017, vol. 73, # 38, p. 5605 - 5612
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Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 23, p. 7122 - 7127
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Reference: [1] European Journal of Organic Chemistry, 2012, # 25, p. 4694 - 4698
[2] Green Chemistry, 2014, vol. 16, # 5, p. 2788 - 2797
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Reference: [1] Synlett, 2006, # 19, p. 3343 - 3345
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  • [ 1112-67-0 ]
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Reference: [1] Patent: US2004/209865, 2004, A1,
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  • [ 198494-75-6 ]
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Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3599 - 3602
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  • [ 2039-82-9 ]
  • [ 201230-82-2 ]
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Reference: [1] European Journal of Organic Chemistry, 2005, # 17, p. 3640 - 3642
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Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 7, p. 1466 - 1468
[2] Organometallics, 2012, vol. 31, # 17, p. 6080 - 6084
[3] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1116 - 1119
[4] Russian Chemical Bulletin, 2012, vol. 61, # 12, p. 2356 - 2359[5] Izv. Akad. Nauk, Ser. Khim., 2012, vol. 61, # 12, p. 2334 - 2336,3
[6] Dalton Transactions, 2014, vol. 43, # 3, p. 1082 - 1095
[7] Russian Chemical Bulletin, 2014, vol. 63, # 10, p. 2243 - 2249[8] Izv. Akad. Nauk, Ser. Khim., 2014, # 10, p. 2243 - 2249,7
[9] Dalton Transactions, 2017, vol. 46, # 1, p. 227 - 241
[10] Journal of the American Chemical Society, 2018, vol. 140, # 12, p. 4430 - 4439
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  • [ 1122-91-4 ]
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Reference: [1] Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877
[2] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 555 - 558
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Reference: [1] Patent: WO2015/181272, 2015, A1,
[2] Patent: US2017/253554, 2017, A1,
[3] Patent: EP3239143, 2017, A2,
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Reference: [1] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 555 - 558
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Reference: [1] Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877
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