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Chemical Structure| 92-69-3 Chemical Structure| 92-69-3

Structure of 92-69-3

Chemical Structure| 92-69-3

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Product Details of [ 92-69-3 ]

CAS No. :92-69-3
Formula : C12H10O
M.W : 170.21
SMILES Code : OC1=CC=C(C2=CC=CC=C2)C=C1
MDL No. :MFCD00002347
InChI Key :YXVFYQXJAXKLAK-UHFFFAOYSA-N
Pubchem ID :7103

Safety of [ 92-69-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318-H410
Precautionary Statements:P273-P280-P301+P312+P330-P305+P351+P338+P310
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 92-69-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 53.9
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.89
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

3.2
Log Po/w (WLOGP)?

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

3.06
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.

3.07
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

3.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.86

Water Solubility

Log S (ESOL):?

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

-3.53
Solubility 0.0504 mg/ml ; 0.000296 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.3
Solubility 0.086 mg/ml ; 0.000505 mol/l
Class?

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

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

-4.33
Solubility 0.00791 mg/ml ; 0.0000465 mol/l
Class?

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

Moderately 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

Yes
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

Yes
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.

-5.07 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

2.0
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

0.0 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)

1.04

Application In Synthesis of [ 92-69-3 ]

* 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 [ 92-69-3 ]

[ 92-69-3 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 330-84-7 ]
  • [ 92-69-3 ]
  • [ 324-94-7 ]
  • [ 134023-60-2 ]
  • [ 80254-62-2 ]
  • 2
  • [ 53592-10-2 ]
  • [ 582-25-2 ]
  • [ 65-85-0 ]
  • copper-powder [ No CAS ]
  • [ 92-69-3 ]
  • [ 108-95-2 ]
  • 5
  • [ 106-41-2 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 92-69-3 ]
YieldReaction ConditionsOperation in experiment
154 mg (91%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
154 mg (91%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
  • 6
  • 2-methylepichlorohydrin [ No CAS ]
  • [ 92-69-3 ]
  • [ 63134-33-8 ]
  • [ 141420-50-0 ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide; Example 3. (Synthesis of compound I- 56 in Table 1) According to similar synthetic method as phenyl glycidyl ether in example 1, 4-benzyloxy-4'-(2-methylglycidyloxy) diphenylsulfone was obtained by reacting with <strong>[63134-33-8]4-benzyloxy-4'-hydroxydiphenylsulfone</strong> and 2-methylepichlorohydrin in sodium hydroxide aqueous solution. Five grams of the compound and 2.3 g of p-phenylphenol were similarly reacted as example 2.
  • 7
  • [ 92-69-3 ]
  • [ 131184-73-1 ]
  • [ 1194551-80-8 ]
  • 9
  • [ 92-69-3 ]
  • [ 19047-31-5 ]
  • [ 745069-44-7 ]
  • 10
  • [ 17642-18-1 ]
  • [ 92-69-3 ]
  • [ 1574542-10-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 0 - 80℃; Step-I: Methyl 2-(biphenyl-4-yloxy)but-2-enoate (intermediate B6-1) [00267] Methyl 2-bromo-2-butenoate (cis/trans) (7.3 g, 40.8 mmol) was added dropwise to a stirring solution of 4-phenylphenol (6.94 g, 40.8 mmol) and K2CO3 (16.91 g, 122 mmol) in acetonitrile (100 mL) at 0 C. After heating at reflux for 16 h at 80 C, the reaction mixture was filtered through a short pad of Celite. The Celite pad was rinsed with acetonitrile prior to concentration of the filtrate under vacuum to afford the title product (11 g, 40.2 mmol, 99% yield) as a light-brownish oil. The crude product was taken to the next step as such. lU NMR (400 MHz, chloroform-d) δ 7.48 - 7.59 (m, 4H), 7.42 (t, J= 7.65 Hz, 2H), 7.32 (d, J= 7.28 Hz, 1H), 6.95 - 7.03 (m, 2H), 6.75 (d, J= 7.03 Hz, 1H), 3.74 (s, 3H), 1.82 (d, J= 7.03 Hz, 3H); MS(ES): m/z 286.2 [M+H20]+.
  • 11
  • [ 92-69-3 ]
  • [ 83883-26-5 ]
  • C28H28O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; The 4 - (6-acryloxy-1-hexyloxy) benzoic acid (corporate SYNTHONChemicals) 29.2g (100mmol), 4-hydroxy-biphenyl 17.0g (100mmol), DMAP0.6g and a small amount of BHT to the mixed suspension under stirring at room temperature in dichloromethane 200 ml in, adding by DCC24.0g (116mmol) dissolved in the dichloromethane 100 ml solution in which a, stirring overnight. Filtering precipitation of urea of DCC, the filtrate for the sequentially 0.5mol/L hydrochloric acid 150 ml, saturated aqueous solution of sodium bicarbonate 150 ml, saturated salt water 150 ml various washing 2 times, after drying with magnesium sulfate, solvent is removed by distillation, recrystallization with ethanol refined, polymerizable compound to obtain a target of (M2) 39.6g (yield 89percent).
  • 12
  • [ 92-69-3 ]
  • [ 108149-63-9 ]
  • 1,1-dimethylethyl (S)-4-[[(3-biphenyloxy)]methyl]-2,2-dimethyl-3-oxazolidinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 80℃; for 3h; General procedure: To a stirred solution of 39 (0.100g, 0.433mmol), appropriate substituted phenol (0.649mmol) and PPh3 (0.182g, 0.693mmol) in anhydrous toluene (5mL) was added DIAD (0.14mL, 0.693mmol) at 80C. After 3h, EtOAc (40mL) was added to the resulting solution. The organic layer was washed with 0.5M aqueous NaOH (40mL) and water (2×40mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5).
  • 13
  • [ 324-94-7 ]
  • [ 92-69-3 ]
 

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