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[ CAS No. 43229-01-2 ] {[proInfo.proName]}

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Chemical Structure| 43229-01-2
Chemical Structure| 43229-01-2
Structure of 43229-01-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 43229-01-2 ]

CAS No. :43229-01-2 MDL No. :MFCD06797599
Formula : C15H12BrNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :PBAAKBQGBSUCTG-UHFFFAOYSA-N
M.W : 350.16 Pubchem ID :11089410
Synonyms :

Calculated chemistry of [ 43229-01-2 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 84.31
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 3.69
Log Po/w (WLOGP) : 3.6
Log Po/w (MLOGP) : 2.14
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.36
Solubility : 0.0152 mg/ml ; 0.0000434 mol/l
Class : Moderately soluble
Log S (Ali) : -4.89
Solubility : 0.00446 mg/ml ; 0.0000127 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.61
Solubility : 0.00087 mg/ml ; 0.00000248 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.63

Safety of [ 43229-01-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 43229-01-2 ]

* 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 [ 43229-01-2 ]
  • Downstream synthetic route of [ 43229-01-2 ]

[ 43229-01-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 14347-05-8 ]
  • [ 43229-01-2 ]
YieldReaction ConditionsOperation in experiment
98% With N,N,N-trimethylanilinium bromide In dichloromethane at 300℃; for 4 h; Step 2: 200 g of Intermediate 1 was added to 1000 ml of dichloromethane, 277 g of trimethylphenylammonium tribromide was added, the temperature was raised to 300 °C, and the reaction was carried out for 4 hours;The residual liquid is added to water, filtered, washed with water, and dried to obtain 253 g of 3-nitrate.Base 4-benzyloxy-2-bromoacetophenone, yield 98percent;
81%
Stage #1: With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 12 h;
Stage #2: With sodium hydrogencarbonate; sodium thiosulfate In tetrahydrofuran; water
1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanone (3): Phenyltrimethylammonium trlbromide (1.46g, 3.90 mmol) was added to a solution of l-(4- benzyloxy-3-nitrophenyl)ethanone (2) (1.04 g. 3.82 mmol) in anhydrous THF (15 niL) in three portions. The reaction mixture was stirred at rt for 12 h. Then an aqueous sodium bicarbonate solution (5percent, 10 mL) and an aqueous sodium thiosulfate solution (10percent, 5 niL) were added. The mixture was extracted with dichloromethane, and combined organics were concentrated by rotary evaporation. The resulting residue was purified by Biotage silica gel column chromatography elutiiig with dichloromethane to give bromo ketone 3 as a white solid (1 ,08 g, 81percent yield): 1H NMR (500 MHz, CDCl3) δ 4.49 (s, 3H), 5.35 (s, 2H), 7.21 (d, I H), 7.40 (m, 5H), 8.15 (dd, IH), 8.49 (d, IH),
75% With N,N,N-trimethylanilinium bromide In tetrahydrofuran at 20℃; for 12 h; Phenyltπmethylammonium tribromide (109.00 g, 290.00 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)ethanone (2) (65.60 g, 242,00 mmol) in anhydrous THF (600 mL) in three portions, and the reaction mixture was stirred at rt for 12 h. The solids were then collected by filtration and the filtrate concentrated. The product w as precipitated from chloroform upon the addition of hexanes, then collected by filtration and dried under vacuum to give bromo ketone 3 as a light yellow solid (63.33 g. 75percent yield): 1H NMR (500 MHz, CDCl3) δ 4.37 (s, 3H), 5,35 (s. 2H), 7,21 (d, IH), 7,40 (m, 5H), 8.15 (dd, IH), 8,49 (d, I H),
75% With bromine In acetic acid at 20℃; To a suspension of 1-(4-(benzyloxy)-3-nitrophenyl)ethanone (9) (13.56 g, 50 mmol) in acetic acid (140 ml) was slowly added bromine (2.8 mL, 55 mmol) in acetic acid (60 ml) at room temperature. The mixture was stirred until the color faded out. Ice water (200 ml) was added to the mixture; the precipitate was ltered and washed with water. Crystallization of the crude solid in ethyl acetate gave the pale yellow crystals (13.1 g, 75percent yield). Mp. 137-138; 1H NMR (400 MHz, CDCl3) δ 8.41 (d, J = 2.3 Hz, 1H), 8.08 (dd, J = 8.8, 2.3 Hz, 1H), 7.42 - 7.25 (m, 5H), 7.15 (d, J = 8.9 Hz, 1H), 5.27 (s, 2H), 4.30 (s, 2H). 13C NMR (101 MHz, CDCl3) δ 188.47, 155.71, 139.86, 134.57, 128.90, 128.65, 126.91, 126.44, 114.90 (s), 71.58 (s), 29.78.

Reference: [1] Patent: CN108358791, 2018, A, . Location in patent: Paragraph 0016; 0020
[2] Canadian Journal of Chemistry, 2011, vol. 89, # 3, p. 364 - 384
[3] Chirality, 2010, vol. 22, # 2, p. 206 - 211
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[5] Tetrahedron Asymmetry, 2000, vol. 11, # 13, p. 2705 - 2717
[6] Patent: WO2007/146869, 2007, A1, . Location in patent: Page/Page column 41; 69
[7] Patent: WO2007/146867, 2007, A2, . Location in patent: Page/Page column 51
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1523 - 1526
[9] Organic Process Research and Development, 2011, vol. 15, # 6, p. 1247 - 1255
[10] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 4, p. 627 - 629
[11] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 8, p. 1294 - 1295
[12] Patent: US5965622, 1999, A,
[13] Patent: CN104086435, 2016, B, . Location in patent: Paragraph 0059; 0062
  • 2
  • [ 6322-56-1 ]
  • [ 43229-01-2 ]
Reference: [1] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 4, p. 627 - 629
[2] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 8, p. 1294 - 1295
[3] Organic Process Research and Development, 2011, vol. 15, # 6, p. 1247 - 1255
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1523 - 1526
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[6] Patent: WO2007/146869, 2007, A1,
  • 3
  • [ 99-93-4 ]
  • [ 43229-01-2 ]
Reference: [1] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 8, p. 1294 - 1295
[2] Acta Crystallographica, Section C: Crystal Structure Communications, 1994, vol. 50, # 4, p. 627 - 629
  • 4
  • [ 100-39-0 ]
  • [ 43229-01-2 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 6, p. 1247 - 1255
[2] Patent: WO2007/146869, 2007, A1,
  • 5
  • [ 100-44-7 ]
  • [ 43229-01-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1523 - 1526
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
  • 6
  • [ 6322-56-1 ]
  • [ 100-44-7 ]
  • [ 43229-01-2 ]
Reference: [1] Patent: CN104086435, 2016, B,
  • 7
  • [ 43229-01-2 ]
  • [ 201677-59-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1523 - 1526
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[3] Patent: US2016/83334, 2016, A1,
[4] Organic Process Research and Development, 1998, vol. 2, # 2, p. 96 - 99
[5] Organic Process Research and Development, 1998, vol. 2, # 2, p. 96 - 99
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