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Chemical Structure| 14180-51-9 Chemical Structure| 14180-51-9

Structure of 14180-51-9

Chemical Structure| 14180-51-9

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Product Details of [ 14180-51-9 ]

CAS No. :14180-51-9
Formula : C20H19O2P
M.W : 322.34
SMILES Code : COC1=CC=C(P(C2=CC=C(OC)C=C2)C3=CC=CC=C3)C=C1
MDL No. :MFCD00048993
InChI Key :BJPHLVZNHDIUNY-UHFFFAOYSA-N
Pubchem ID :518897

Safety of [ 14180-51-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 14180-51-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 18
Fraction Csp3 0.1
Num. rotatable bonds 5
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 98.13
TPSA ?

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

32.05 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.87
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

4.55
Log Po/w (WLOGP)?

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

3.46
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.

4.16
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

5.52
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.31

Water Solubility

Log S (ESOL):?

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

-4.95
Solubility 0.00358 mg/ml ; 0.0000111 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.95
Solubility 0.00365 mg/ml ; 0.0000113 mol/l
Class?

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

Moderately 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

-7.77
Solubility 0.00000542 mg/ml ; 0.0000000168 mol/l
Class?

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

Poorly 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

Yes
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

Yes
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.

-5.04 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

1.0
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

0.0
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)

3.79

Application In Synthesis of [ 14180-51-9 ]

* 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.

  • Downstream synthetic route of [ 14180-51-9 ]

[ 14180-51-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 20057-88-9 ]
  • [ 14180-51-9 ]
  • [ 14180-52-0 ]
  • [ 882-33-7 ]
  • 3
  • [ 14180-51-9 ]
  • [ 92025-79-1 ]
  • [ 84127-04-8 ]
  • [ 829-85-6 ]
  • 4
  • [ 1940-57-4 ]
  • [ 14180-51-9 ]
  • Bis-(p-anisyl)-monophenylfluorenyl-(9)-phosphoniumbromid [ No CAS ]
  • 5
  • [ 14180-51-9 ]
  • [ 799-55-3 ]
YieldReaction ConditionsOperation in experiment
96% With dihydrogen peroxide; In acetone; at 20℃; for 1h; 5 g of compound 2a was transferred to a round bottom flask, 50 ml of acetone was added, and H2O2 (1.1 eq) was slowly added dropwise. Stir at room temperature Mix for 1 h, vacuum distillation of acetone. The crude product was dissolved in dichloromethane and saturated brine was washed until the KI test paper was kept blue. The methylene chloride was distilled off to give the product as an oil. After standing overnight, the oily substance was crystallized and recrystallized from cyclohexane as a solvent to give a white solid in 96% yield.
  • 6
  • [ 104-92-7 ]
  • [ 644-97-3 ]
  • [ 14180-51-9 ]
YieldReaction ConditionsOperation in experiment
78% The magnesium powder was washed with hydrochloric acid and acetone separately, and dried. THF was refluxed with metal Na to benzophenone to become dark purple. The new Mg powder was added to the reaction apparatus, N2 was replaced three times, and I2 granules and purified THF were successively added. N2, the dried compound 1a (4-bromoanisole) was transferred to a dropping funnel. The reaction was initiated by heating, and the THF solution of 4-bromoanisole was slowly added dropwise.After completion of the dropwise addition, the mixture was stirred at room temperature for 1 h to give a dark black mixture. Benzyl phosphorus dichloride slowly added to the Grignard reagent, dropping finished, stirring 2h. The reaction mixture was slowly added to a 10% aqueous solution of ice water and extracted with ether. The solvent was evaporated under reduced pressure to give a crude product as a yellow solid. The crude product was recrystallized from ethanol to give a white solid. Yield: 78%.
175.3 g Grignard reagent was prepared using 4-bromoanisole (TokyoChemical Industry Co., Ltd., trade CD: B0547) 374.6g, magnesium (Sigma-AldrichJapan joint company, trade CD: 219-0040-5) 65.4g and dehydrated THF (Kanto ChemicalCo., Inc. Ltd., product CD: 41001-75) 3L. Then, a solution of dichlorophenylphosphine (Tokyo Chemical Industry Co.,Ltd., trade CD: P0207) 179g dissolved in dehydrated THF500mL was slowly added.The reaction solution was filtered, concentrated, and dissolved by adding chloroform(Sigma-Aldrich Japan joint company made: Product CD: 205-3410-8) 2L. Thechloroform solution was extracted 4 times with purified water 500 mL. Theresulting chloroform layer was dried over magnesium sulfate (Sigma-Aldrich JapanLLC, trade CD: 219-0510-5), and the precipitate was filtered, and the filtratewas concentrated. The resulting concentrate was recrystallized with ethanol(Sigma-Aldrich Japan joint company, trade CD: 209-0780-3) 350mL, then driedunder reduced pressure to obtain 175.3g of bis(4-methoxy-phenyl) phenyl phosphine.
  • 7
  • [ 14180-51-9 ]
  • Bis-p-anisylbenzylphenylphosphonium [ No CAS ]
  • 8
  • [ 14180-51-9 ]
  • [ 100-44-7 ]
  • Bis-p-anisylbenzylphenylphosphonium [ No CAS ]
  • 9
  • [ 104-92-7 ]
  • [ 1079-66-9 ]
  • [ 14180-51-9 ]
  • 10
  • [ 14180-51-9 ]
  • [ 76943-18-5 ]
  • C24H23F6O4P [ No CAS ]
  • 11
  • [ 14180-51-9 ]
  • [ 100-39-0 ]
  • Benzyl[bis(4-methoxyphenyl)]phenylphosphonium bromide [ No CAS ]
  • 14
  • [ 14180-51-9 ]
  • selenium [ No CAS ]
  • C20H19O2PSe [ No CAS ]
  • 15
  • [ 14180-51-9 ]
  • disodium bis(4-methoxy-3-sulfonatophenyl)phenylphosphane [ No CAS ]
  • 16
  • [ 14180-51-9 ]
  • N-trichloroacetylfluoroacetimidoyl chloride [ No CAS ]
  • (Z)-di(4-methoxyphenyl)phenyl(1-trichloroacetamido-2-fluorovinyl)phosphonium chloride [ No CAS ]
  • (E)-di(4-methoxyphenyl)phenyl(1-trichloroacetamido-2-fluorovinyl)phosphonium chloride [ No CAS ]
  • 17
  • [ 644-97-3 ]
  • [ 82303-13-7 ]
  • [ 14180-51-9 ]
  • 18
  • [ 14180-51-9 ]
  • Benzyl[bis(4-hydroxyphenyl)]phenylphosphonium bromide [ No CAS ]
  • 19
  • [ 14180-51-9 ]
  • Bis-(p-anisyl)-mono-phenylphosphonium-9-fluorenylid [ No CAS ]
  • 20
  • [ 12107-56-1 ]
  • [ 14180-51-9 ]
  • [ 84914-25-0 ]
  • 22
  • potassium tetrathiocyanatopalladate [ No CAS ]
  • [ 14180-51-9 ]
  • [ 105154-72-1 ]
  • 23
  • potassium tetrathiocyanatopalladate [ No CAS ]
  • [ 14180-51-9 ]
  • Pd(SCN)2(Ph(PC6H4-OCH3-p)2)2 [ No CAS ]
  • 24
  • potassium tetrachloropalladate(II) [ No CAS ]
  • [ 14180-51-9 ]
  • [ 84914-25-0 ]
  • 25
  • [ 15243-33-1 ]
  • [ 14180-51-9 ]
  • Ru3*9CO*3P(C6H5)(C6H4OCH3)2 = [Ru3(CO)9(P(C6H5)(C6H4OCH3)2)3] [ No CAS ]
  • 26
  • chloroauric acid [ No CAS ]
  • [ 14180-51-9 ]
  • [ 252652-41-8 ]
  • 27
  • [ 59967-36-1 ]
  • [ 14180-51-9 ]
  • [ 252650-76-3 ]
  • 28
  • [ 13463-40-6 ]
  • [ 14180-51-9 ]
  • [ 252651-11-9 ]
  • 29
  • [ 12080-32-9 ]
  • [ 14180-51-9 ]
  • [ 252651-95-9 ]
  • 30
  • [ 14057-91-1 ]
  • [ 14180-51-9 ]
  • [ 177190-81-7 ]
  • 31
  • [ 866343-75-1 ]
  • [ 14180-51-9 ]
  • [ 959428-40-1 ]
  • 32
  • [ 15243-33-1 ]
  • [ 14180-51-9 ]
  • [ 1253691-12-1 ]
  • 33
  • [ 75-09-2 ]
  • Ru3(CO)10(μ-Ph2PCH2CH2AsPh2) [ No CAS ]
  • [ 14180-51-9 ]
  • C55H43AsO11P2Ru3*0.5CH2Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.95% General procedure: A mixture of Ru3(CO)10(arphos) (52.3mg, 0.051mmol) and PCy3 (14.0mg, 0.051mmol) was heated in refluxing hexane (25ml) for 1h. Completion of the reaction was monitored by TLC. The solvent was removed under reduced pressure. The reaction mixture was separated by preparative TLC (2:3 dichloromethane:hexane), affording three bands. The first band (Rf=0.76) gave the starting material Ru3(CO)10(arphos), the second band (Rf=0.57) gave the major product, characterised as Ru3(CO)9(arphos)PCy3, and the third band was only obtained in trace amounts and was not characterised. The results are as follows. Yield: 21.7mg (33.28%),
  • 34
  • [ 84330-43-8 ]
  • [ 75-09-2 ]
  • [ 14180-51-9 ]
  • C54H41As2O11PRu3*0.15CH2Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
All manipulations were performed under a dry oxygen-free dinitrogen atmosphere using standard Schlenk techniques, under nitrogen atmosphere. Tris (4-methylphenyl) phosphine was used as ligand, and μ-bis (diphenylarsino) methane decacarbonyltriruthenium(0) was prepared by two step route.[25] The title compound was obtained by refluxing equimolar quantities of Ru3(CO)10(μ-Ph2AsCH2AsPh2) (105.5 mg, 0.1 mmol) and tris (4-methoxyphenyl) phosphine (32.23 mg, 0.1 mmol) in hexane under a nitrogen atmosphere. Crystals suitable for Xray diffraction were grown by slow solvent/solvent diffusion of CH3OH into CH2Cl2.
  • 35
  • [ 14180-51-9 ]
  • [ 74427-22-8 ]
  • (E)-ethene-1,2-diylbis(bis(4’-methoxylphenyl)phenylphosphonium)ditriflate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% at 120℃; for 6h;Inert atmosphere; Schlenk technique; General procedure: A. TfOCH2CF2H(0.514 g, 2.4 mmol) and triphenylphosphine (0.525 g, 2 mmol) were placed in aclosed Schlenk flask under a N2 atmosphere. The mixture was stirredat 120 oC for 24 h and cooled to room temperature. The resultingsolid was washed by diethyl ether, recrystallized from CH2Cl2/hexane,and dried in vacuum to give 0.66 g of (E)-ethene-1,2-diylbis(triphenylphosphonium)ditriflate (3a) as a white solid (0.78 mmol, 78%).2
 

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