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Chemical Structure| 175883-62-2 Chemical Structure| 175883-62-2

Structure of 175883-62-2

Chemical Structure| 175883-62-2

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Product Details of [ 175883-62-2 ]

CAS No. :175883-62-2
Formula : C8H11BO3
M.W : 165.98
SMILES Code : COC1=C(C)C=C(C=C1)B(O)O
MDL No. :MFCD02179464
InChI Key :PXVDQGVAZBTFIB-UHFFFAOYSA-N
Pubchem ID :2773487

Safety of [ 175883-62-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 175883-62-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 47.73
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

49.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.16
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.32
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.33
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.17

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.84
Solubility 2.41 mg/ml ; 0.0145 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.8
Solubility 2.64 mg/ml ; 0.0159 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.79
Solubility 2.66 mg/ml ; 0.016 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.49 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.58

Application In Synthesis of [ 175883-62-2 ]

* 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.

  • Downstream synthetic route of [ 175883-62-2 ]

[ 175883-62-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 175883-62-2 ]
  • [ 175883-55-3 ]
  • 1,2-difluoro-4-(4-methoxy-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene [ No CAS ]
  • 2
  • [ 19190-91-1 ]
  • [ 175883-62-2 ]
  • [ 303764-13-8 ]
  • 4
  • [ 175883-62-2 ]
  • [ 487944-81-0 ]
  • 2,7-diisopropoxy-1-(4-methoxy-3-methylphenyl)naphthalene [ No CAS ]
  • 1-bromo-2,7-diisopropoxy-8-(4-methoxy-3-methylphenyl)naphthalene [ No CAS ]
  • [ 487945-04-0 ]
  • 5
  • [ 175883-62-2 ]
  • [ 216485-72-2 ]
  • (1-ethyl-5-hydroxy-1<i>H</i>-pyrazol-4-yl)-(6-methanesulfonyl-4'-methoxy-2,3'-dimethyl-biphenyl-3-yl)-methanone [ No CAS ]
  • 7
  • [ 175883-62-2 ]
  • 4-bromo-1-methoxy-2-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-benzene [ No CAS ]
  • 4,4'-dimethoxy-3'-methyl-3-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-biphenyl [ No CAS ]
  • 8
  • [ 626-05-1 ]
  • [ 175883-62-2 ]
  • 2,6-bis-(4-methoxy-3-methyl-phenyl)-pyridine [ No CAS ]
  • 9
  • [ 623-00-7 ]
  • [ 175883-62-2 ]
  • 4'-methoxy-3'-methyl-biphenyl-4-carbonitrile [ No CAS ]
  • 10
  • [ 14371-10-9 ]
  • [ 175883-62-2 ]
  • C17H18O2 [ No CAS ]
  • C17H18O2 [ No CAS ]
  • 11
  • [ 175883-62-2 ]
  • [ 504-63-2 ]
  • C11H14BBrO3 [ No CAS ]
  • 12
  • [ 950180-17-3 ]
  • [ 175883-62-2 ]
  • C27H30ClNO4 [ No CAS ]
  • 13
  • C17H20INO3S [ No CAS ]
  • [ 175883-62-2 ]
  • C25H29NO4S [ No CAS ]
  • 14
  • [ 868262-22-0 ]
  • [ 175883-62-2 ]
  • C28H33NO5S [ No CAS ]
  • 15
  • [ 175883-62-2 ]
  • N,N'-4,4'-bis(benzyl-6-methoxy-3-boronic acid)-bipyridinium dibromide [ No CAS ]
  • 16
  • [ 175883-62-2 ]
  • [ 460748-07-6 ]
  • 17
  • [ 175883-62-2 ]
  • 4-(7-methyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile [ No CAS ]
  • 18
  • [ 175883-62-2 ]
  • [ 460748-08-7 ]
  • 19
  • [ 175883-62-2 ]
  • 3'-methyl-3-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-biphenyl-4,4'-diol [ No CAS ]
  • 20
  • [ 175883-62-2 ]
  • 4,4'-bis-allyloxy-3'-methyl-3-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-biphenyl [ No CAS ]
  • 21
  • [ 175883-62-2 ]
  • 3-[4'-(2,3-dihydroxypropyloxy)-3-(1H,1H,2H,2H,3H,3H-perfluorononyl)-3'-methylbiphenyl-4-yloxy]propane-1,2-diol [ No CAS ]
  • 22
  • [ 175883-62-2 ]
  • 5,6-Bis(4-hydroxy-3-methylphenyl)acenaphthene [ No CAS ]
  • 23
  • [2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino}-acetic acid tert-butyl ester [ No CAS ]
  • [ 175883-62-2 ]
  • [2-(3-isobutyl-4'-methoxy-3'-methylbiphenyl-4-yloxy)ethyl]-methylamino}-acetic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Dissolve f [2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino}-acetic acid tert- butyl ester (2 g, 4.99 mmol) in dry tetrahydrofuran (20 mL). Deliver an aliquot of this stock solution (4 mL, 0.999 mmol) under nitrogen to a solution in tetrahydrofuran (5 mL) of the appropriate arylboronic acid (1.5 eq), palladium acetate (22 mg, 0.1 eq; 0.099 mmol), tricyclohexylphosphine (34 mg, 0.12 eq; 0.1198 mmol) and potassium fluoride (180 mg, 3.1 eq; 3.098 mmol). Stir at reflux for 66 h. Monitor the progress of the reactions after 66 h and treat each reaction then individually as described. Deliver an aliquot of [2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino)-acetic acid tert-butyl ester (0.999 mmol of the stock solution), along with (4-methoxy-3-methyl) boronic acid (248 mg, 1.4939 mmol, 95% pure), palladium acetate (22 mg), tricyclohexylphosphine (34 mg, 0.12 eq; 0.1214 mmol) and potassium fluoride (180 mg, 3.098 mrnol). Add a second aliquot of reagents after 66 h (4-methoxy-3-methyl) boronic acid (248 mg, 1.4939 mmol), tricyclohexylphosphine (37 mg, 0.1319 mmol), palladium acetate (24 mg) and potassium fluoride (186 mg, 3.20 mmol). Stir for another 24 h. Dilute with tetrahydrofuran (dry, 4 mL) and treat with [1,1'-bis(diphenylphosphino)-ferrocene)- dichloropalladium (II) complex (DPPF) (76 mg, 0.093 eq), 2 N aqueous potassium carbonateaq (5 eq, 2.5 mL) and (4-methoxy-3-methyl) boronic acid (166 mg) and stir at reflux for 24 h until total consumption of the starting material as indicated by thin layer chromatography and LC-MS. Filter the crude reaction mixture through a -wet CeliteNo. pad, dilute with ethyl acetate (50 mL), wash the organic, phase with water (50 mL), dry (magnesium sulfate), filter, concentrate and purify (HPLC, eluting with 10:90 ethyl acetate: hexanes) to give the title compound (302.8 mg, 62%). ¹H NMR (400 MHz, CDC13) 8 7.36-7.32 (m, 3H), 7.28-7.27 (m, 1H), 6.8 8 (d, J = 8.3 Hz, 2H), 4.13 (m, 2H), 3.87 (s, 3H), 3.36 (s, 2H), 3.05 (t, J =.5.7 Hz, 2H), 2.55-2.53 (m, 5H), 2.29 (s, 3H), 1.96 (q, J = 6.6 Hz, 1H, ), 1.49 (s, 9H), 0.94 (d, J = 6.6 Hz, 6H,); LC-MS: mz = 442.0
  • 24
  • [ 619-58-9 ]
  • [ 175883-62-2 ]
  • [ 71-36-3 ]
  • [ 885965-61-7 ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate;tetrakis(triphenylphosphine)palladium (0); In water; ethyl acetate; toluene; Step 1: 3-Methyl-4-methoxyphenylboronic acid (542 mg) was combined with 4-iodobenzoic acid (810 mg), cesium carbonate (5.32 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg) was added. The reaction was heated to 80 C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The layers were separated and the organics were concentrated to dryness. The residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes) giving 3'-methyl-4'-methoxy-4-biphenylcarboxylic acid (240 mg). Yield=30%
  • 25
  • [ 15231-91-1 ]
  • [ 175883-62-2 ]
  • [ 550998-12-4 ]
YieldReaction ConditionsOperation in experiment
1.56 g (73%) 6-(4-Methoxy-2-methylphenyl)-2-naphthol The title compound was prepared by reacting 6-bromo-2-naphthol (1.8 g, 5.4 mmol) with <strong>[175883-62-2]4-methoxy-3-methylphenylboronic acid</strong> (1.74 g, 7.0 mmol) according to method A to yield 1.56 g (73%) of yellowish solid: mp 124-126 C.; 1H NMR (DMDO-d6): delta 2.25(3H,s), 3.78 (3H, s), 6.85 (1H, dd, J=8.35 Hz, J=2.56 Hz), 6.90 (1H, d, J=2.37 Hz), 7.09 (1H, dd, J=8.75 Hz, J=2.25 Hz), 7.13 (1H, s), 7.20 (1H, d, J=8.33 Hz), 7.35 (1H, dd, J=8.39 Hz, J=1.37 Hz), 7.67 (1H,s), 7.70 (1H, d, J=8.53 Hz), 7.78 (1H, d, J=8.78 Hz), 9.74 (1H, s); MS (ESI) m/z263 (M-H)-. Anal. for C18H16O2: Calc'd: C: 81.79H: 6.10 Found: C: 81.43H: 6.01
  • 26
  • [ 175883-62-2 ]
  • [ 171178-33-9 ]
  • [ 897360-67-7 ]
YieldReaction ConditionsOperation in experiment
77% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 2h;Heating / reflux; To a solution of 6~chloro-pyrido[3,2-d]pyrimidin-4(3H)one (1.94 mmole) in 1 ,4- dioxane (40 ml) and water (20 ml) was added 4-methoxy-3-methylphenyl boronic acid (2.33 mmole), potassium carbonate (4.85 mmole) and tetrakis(tri- phenylphosphine)palladium(O) (0.097 mmole). The reaction mixture was refluxed for two hours, cooled to room temperature and the solvents were evaporated in vacuo. The residue was adsorbed on silica and purified by silica gel column chromatography (the mobile phase being a methanol/dichloromethane mixture in a ratio of 3:97), affording the title compound as a pure white powder (398 mg, yield 77 %) which was characterized by its mass spectrum as follows: MS (m/z) : 268 ([M+H]+, 100).
  • 27
  • [ 1028331-34-1 ]
  • [ 175883-62-2 ]
  • [ 1028424-71-6 ]
  • 28
  • [ 1028424-64-7 ]
  • [ 175883-62-2 ]
  • [ 1028424-66-9 ]
  • 29
  • [ 175883-62-2 ]
  • [ 850364-08-8 ]
  • [ 1056265-63-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine;copper diacetate; In dichloromethane; for 41h;Molecular sieve; Description 34; 1 -[3-Methyl-4-(methyloxy)phenyl]-4-[(phenylmethyl)oxy]-1 H-indazole (D34)The 4-[(phenylmethyl)oxy]-1 H-indazole (D1) (500 mg, 2.23 mmol), the [3-methyl-4- (methyloxy)phenyl]boronic acid (740 mg, 4.46 mmol), copper (II) acetate (608 mg, 3.345 mmol), pyridine (0.36 mL, 4.46 mmol) and powdered molecular sieves (400 mg) in DCM (75 mL) were stirred at room temperature in the presence of air. After 41 hours the mixture <n="34"/>was filtered through a pad of celite and washed with water. The aqueous was re-extracted with DCM and the combined organics were washed with brine and dried over MgSO4. The crude (1.17 g) was purified by flash chromatography (Biotage SP4) with a gradient of EtOAc 0 to 30% in hexane to afford 562 mg of title compound (D34) containing an impurity. LC-MS: MH+ = 345 (C22H20N2O2 = 344)
  • 30
  • [ 1052271-60-9 ]
  • [ 175883-62-2 ]
  • [ 1059098-72-4 ]
YieldReaction ConditionsOperation in experiment
17% With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Heating / reflux; Example 24; 8-(4-methoxy-3-methyl phenyl)H-imidazo[1,5-a]pyridine8-bromo-H-imidazo[1,5-a]pyridine (0.1 g, 0.5 mmol, 1 eq) was dissolved in 10 mL of DME and kept under an argon atmosphere. To that solution [Pd(PPh3)4] (0.025 mmol, 0.05 eq), 4-methoxy-3-methylphenyl boronic acid (0.124 g, 0.75 mmol, 1.5 eq) and an aqueous NaOH solution (0.2M, 5 mL) were added under stirring. The resulting mixture was refluxed for 24 h. After cooling, the mixture was diluted with water and the aqueous layer was extracted with CHCl3. The organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure. Semi-preparative HPLC-chromatography afforded the pure product.Yield: 0.020 g (17%), 1H-NMR, 500 MHz, CDCl3: delta 2.29 (s, 3H); 3.90 (s, 3H); 6.94-6.96 (m, 1H); 7.08-7.10 (m, 2H); 7.35 (s, 1H); 7.39-7.41) m, 1H); 7.88 (s, 1H); 8.29 (bs, 1H); 9.52 (bs, 1H), MS: m/z 239.2 [M+H]+; HPLC: Method [B], (214 nm), rt: 6.68 min (88.3%)
  • 31
  • [ 107346-32-7 ]
  • [ 175883-62-2 ]
  • 4-amino-8-(4-methoxy-3-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% EXAMPLE 73 4-amino-8-(4-methoxy-3-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (125 mg, 0.40 mmol) and <strong>[175883-62-2](4-methoxy-3-methylphenyl)boronic acid</strong> (133 mg, 0.80 mmol) were reacted to afford the title compound (105 mg, 75% yield) as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.59 (bs, 1H), 7.76-7.82 (m, 2H), 7.67-7.72 (m, 1H), 7.53 (dd, J=8.2, 2.2 Hz, 1H), 7.46 (m, 1H), 6.96 (d, J=8.2, 1H), 3.89 (s, 3H), 3.46 (apparent q, J=6.7 Hz, 2H), 2.30 (s, 3H), 1.67 (apparent sextet, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=351 (M+H) HPLC 1.88 min.
  • 32
  • [ 122775-34-2 ]
  • [ 175883-62-2 ]
  • C17H14O3 [ No CAS ]
  • 33
  • [ 175883-62-2 ]
  • [ 219838-95-6 ]
  • C15H20O4 [ No CAS ]
  • C15H20O4 [ No CAS ]
  • [ 1155875-37-8 ]
  • 34
  • [ 175883-62-2 ]
  • [ 219838-95-6 ]
  • C12H16O2 [ No CAS ]
  • 2-(4-methoxy-3-methylphenyl)but-3-en-1-ol [ No CAS ]
  • [ 1155875-52-7 ]
  • 35
  • [ 1078734-22-1 ]
  • [ 175883-62-2 ]
  • [ 1193525-72-2 ]
 

Historical Records

Technical Information

Categories

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[ 175883-62-2 ]

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