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Chemical Structure| 2444-90-8 Chemical Structure| 2444-90-8

Structure of 2444-90-8

Chemical Structure| 2444-90-8

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Product Details of [ 2444-90-8 ]

CAS No. :2444-90-8
Formula : C15H14Na2O2
M.W : 272.25
SMILES Code : CC(C1=CC=C([O-])C=C1)(C2=CC=C([O-])C=C2)C.[Na+].[Na+]
MDL No. :MFCD01763349
InChI Key :WGMBWDBRVAKMOO-UHFFFAOYSA-L
Pubchem ID :17127

Safety of [ 2444-90-8 ]

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

Computational Chemistry of [ 2444-90-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.2
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 65.66
TPSA ?

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

46.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-20.85
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

3.32
Log Po/w (WLOGP)?

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

4.3
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.

3.2
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

3.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.35

Water Solubility

Log S (ESOL):?

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

-3.95
Solubility 0.0302 mg/ml ; 0.000111 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.

-3.96
Solubility 0.0295 mg/ml ; 0.000108 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

-4.59
Solubility 0.00692 mg/ml ; 0.0000254 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

Yes
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.

-5.6 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

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<0.0
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)

1.52

Application In Synthesis of [ 2444-90-8 ]

* 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 [ 2444-90-8 ]

[ 2444-90-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 80-05-7 ]
  • [ 2444-90-8 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide; potassium carbonate In water at 100℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous K2CO3 solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.; EXAMPLE 27; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 35percent aqueous K2CO3 solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
95% With sodium hydroxide; potassium hydrogencarbonate In water at 100℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 20percent aqueous KHCO3 solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
94% With sodium hydroxide In isopropyl alcohol at 60℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isopropyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.
94% With sodium hydrogencarbonate; sodium carbonate In water at 100℃; for 1 h; 0.01 Mole of bisphenol A, 0.021 mole of Na2CO3 and 200 mL of 8.4percent aqueous sodium bicarbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.
94% With sodium hydroxide In butan-1-ol at 50℃; for 4 h; 0.01 Mole of bisphenol A, 0.0205 mole of NaOH and 100 mL of n-butyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 50° C. for 4 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 50 mL of hot n-butyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.
94% With sodium hydroxide In 2-methyl-propan-1-ol at 60℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isobutyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isobutyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.
92% With sodium hydroxide In propan-1-ol at 60℃; for 3 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of n-propyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 3 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot n-propyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was measured by titration to be 99.9percent.
92% With sodium hydroxide In acetone at 60℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of acetone were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot acetone, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was 99.9percent.
90% With sodium hydroxide; sodium carbonate In water at 100℃; for 1 h; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 24.6 g of bis-sodium salt of bisphenol A. The yield was 90percent, and the purity was 99.7percent.; EXAMPLE 24; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 18percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 93percent, and the purity was 99.9percent.

References: [1] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4-5.
[2] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4.
[3] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2.
[4] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4.
[5] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 3.
[6] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2.
[7] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2.
[8] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 3.
[9] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4.
[10] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 10, p. 1953 - 1956[11] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 10, p. 2175 - 2178.
[12] Patent: US2005/49439, 2005, A1, . Location in patent: Page/Page column 12; 13.
[13] Patent: US4202993, 1980, A, .
[14] Patent: WO2015/160931, 2015, A1, . Location in patent: Paragraph 0067.
 

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