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Chemical Structure| 1080-32-6 Chemical Structure| 1080-32-6

Structure of 1080-32-6

Chemical Structure| 1080-32-6

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Product Details of [ 1080-32-6 ]

CAS No. :1080-32-6
Formula : C11H17O3P
M.W : 228.22
SMILES Code : O=P(CC1=CC=CC=C1)(OCC)OCC
MDL No. :MFCD00009078
InChI Key :AIPRAPZUGUTQKX-UHFFFAOYSA-N
Pubchem ID :14122

Safety of [ 1080-32-6 ]

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

Computational Chemistry of [ 1080-32-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.45
Num. rotatable bonds 6
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 61.47
TPSA ?

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

45.34 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.41
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

1.7
Log Po/w (WLOGP)?

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

3.3
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.

2.1
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

1.95
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.29

Water Solubility

Log S (ESOL):?

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

-2.23
Solubility 1.36 mg/ml ; 0.00594 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.

-2.27
Solubility 1.23 mg/ml ; 0.0054 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

-3.89
Solubility 0.0293 mg/ml ; 0.000128 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

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

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

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

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

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)

3.38

Application In Synthesis of [ 1080-32-6 ]

* 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 [ 1080-32-6 ]

[ 1080-32-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 108-86-1 ]
  • [ 3167-63-3 ]
  • [ 1080-32-6 ]
  • 2
  • [ 14615-72-6 ]
  • [ 1080-32-6 ]
  • [ 133156-35-1 ]
  • (Z)-1-<3,5-bis(benzyloxy)phenyl>-2-phenylethene [ No CAS ]
  • 4
  • [ 1080-32-6 ]
  • [ 63874-95-3 ]
  • (E)-1-benzyl-4-(2-phenylethenyl)pyrazole [ No CAS ]
  • 5
  • [ 1080-32-6 ]
  • [ 118289-17-1 ]
  • [ 1256724-95-4 ]
YieldReaction ConditionsOperation in experiment
37% Intermediate 17(E)-2-Bromo-4-styrylpyridine. To a solution of diethyl benzylphosphonate (4.57 mL, 21.91 mmol) in dimethylformamide (50 mL) at room temperature was added sodium methoxide (2.367 g, 43.8 mmol) and 18-Crown-6 (2.316 g, 8.76 mmol). After stirring at room temperature for 5 min, the reaction was cooled to 0°C and treated with 2-bromoisonicotinaldehyde (4.89 g, 26.3 mmol) as a solid in one portion. The ice bath was removed and the reaction stirred at room temperature for 1 h. The reaction was gradually warmed to 120°C and held there for 2 h. The reaction was cooled to room temperature and poured into water (500 mL) with vigorous stirring. The resulting suspension was extracted with diethyl ether (3X), washed with water, then brine, dried over magnesium sulfate, and concentrated to an oil. The resulting residue was purified by column chromatography (6percent EtOAc/Hex- > 12percent EtO Ac/Hex) to give 2.12 g (37percent) as an oil. 3/4-NMR (CDCI3, 500 MHz) delta 8.35 (d, J=5.2, IH), 7.52-7.62 (m, 3H), 7.43 (m, 2H), 7.30-7.40 (m, 3H), 6.98 (d, J=16.2, IH) 13C-NMR (CDCI3, 126 MHz) delta 150.4, 147.7, 143.1, 135.8, 134.8, 129.3, 129.0, 127.3, 125.0, 124.6, 120.1.
  • 6
  • [ 1080-32-6 ]
  • [ 118289-17-1 ]
  • tert-butyl (1R,2R)-1-(2-bromopyridin-4-yl)-2-hydroxy-2-phenylethylcarbamate [ No CAS ]
  • C18H21BrN2O3 [ No CAS ]
  • 7
  • [ 51738-07-9 ]
  • [ 1080-32-6 ]
  • (E)-1-chloro-3-iodo-2-(β-styryl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% General procedure: To a flame-dried 100 mL round-bottom flask NaHMDS (2 mmol, 1 eq) in THF (5 mL) were addedand the solution was cooled down to 0 C. A solution of the corresponding benzyl phosphonate(II) (2 mmol, 1 eq) in THF (12 mL) was added dropwise under stirring. The reaction was stirred fora further 10 min at 0 C, then a solution of the haloaldehyde (I) (2 mmol, 1 eq) in THF (4 mL) wasadded dropwise. The mixture was allowed to warm from 0 C to room temperature 12-14 h understirring. The reaction mixture was quenched with water (10 mL). The aq layer was extracted withEt2O (3 x 10 mL). The combined organic layers were washed with 10% aq NaHSO3 (2 x 5 mL)and then with brine (10 mL). The combined organic layers were dried over Na2SO4 andconcentrated by evaporation in vacuo to give 10a-c. (10a: E/Z: 10:1, 10b: E, 10c: E/Z: 20:1). TheE-isomers of compounds 10a?-c? was obtained using column chromatography (2.0% EtOAc inpetroleum ether) from mixtures of 10a-c. The E/Z ratio was determined by 1H NMR.
  • 8
  • [ 1080-32-6 ]
  • [ 89891-69-0 ]
  • 3-bromo-4-styrylbenzonitrile [ No CAS ]
  • 3-bromo-4-styrylbenzonitrile [ No CAS ]
 

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