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Chemical Structure| 2173-69-5 Chemical Structure| 2173-69-5

Structure of 2173-69-5

Chemical Structure| 2173-69-5

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Product Details of [ 2173-69-5 ]

CAS No. :2173-69-5
Formula : C10H14O
M.W : 150.22
SMILES Code : CC(C)(CO)C1=CC=CC=C1
MDL No. :MFCD00506139
Boiling Point : No data available
InChI Key :ZVSCENGNXWPDPL-UHFFFAOYSA-N
Pubchem ID :219535

Safety of [ 2173-69-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 2173-69-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 46.87
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.

2.23
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

2.89
Log Po/w (WLOGP)?

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

1.96
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.

2.49
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

2.37
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.39

Water Solubility

Log S (ESOL):?

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

-2.86
Solubility 0.206 mg/ml ; 0.00137 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.

-2.97
Solubility 0.159 mg/ml ; 0.00106 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

-3.03
Solubility 0.14 mg/ml ; 0.000931 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

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.

-5.16 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)

1.0

Application In Synthesis of [ 2173-69-5 ]

* 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 [ 2173-69-5 ]

[ 2173-69-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 57625-74-8 ]
  • [ 2173-69-5 ]
YieldReaction ConditionsOperation in experiment
99% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 3h; Methyl 2-methyl-2-phenylpropanoate (10.8 g, 60.6 mmol, Eq: 1.00) in tetrahydrofuran (193 ml) was cooled to 0 C., lithium aluminium hydride was added (30.3 ml, 60.6 mmol, Eq: 1.00) via a syringe over 5 minutes. The mixture was stirred at 0 C. for 3 hours, and 2.3 ml water was added over 2 minutes. The mixture was stirred for 10 minutes, 2.3 ml 1N NaOH was added, the mixture was stirred for 5 minutes (a gel forms), 7 ml water was added, the mixture was stirred for 15 minutes, filtered through a pad of celite. The celite was washed with ether and the solvent was removed under vacuum to give methyl-2-phenyl-propan-1-ol (51) (9.0 g, 99%) as a clear oil. [0351] 1H NMR (400 MHz, dimethyl sulfoxide-d6) delta ppm 1.23 (s, 6H) 3.43 (d, J=5.27 Hz, 2H) 4.66 (t, J=5.27 Hz, 1H) 7.06-7.51 (m, 5H).
With sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 5h; Methyl-2,2-dimethyl-2-phenyl acetate (Intermediate 2) (0.5 kg), and THF (2.5 LTR) were charged to a reactor, and sodium borohydride (100 gms) was added in lots. The mixture was stirred at room temperature for 5 hours. After completion of the reaction, the pH was adjusted to 3-4 with HC1, the inorganics filtered and the filtrate concentrated and stripped with toluene (50 ml) to obtain the title compound as an oil weighing 400 gms.
3.8 g (81%) With aq NaOH; In water; Part B. Preparation of 2,2-(Dimethyl)-2-phenylethyl alcohol. To a cooled (0 C.) solution of 1M lithium aluminum hydride in ether (31.1 mL, 31.1 mmol) was added methyl 2,2-(dimethyl)-2-phenylacetate (5.54 g, 31.1 mmol) as a solution in ether. The reaction mixture was allowed to warm to 25 C. and was stirred for 3 h. The mixture was cooled to 0 C. and was quenched by slow sequential addition of 1.2 mL of water, 1.2 mL of 15% aq NaOH and 3.6 mL of water. The resulting slurry was stirred vigorously with warming to 25 C. for 1 h, and then was dried (MgSO4), filtered and concentrated to afford 3.8 g (81%) of the title compound.
  • 2
  • [ 2173-69-5 ]
  • [ 108-24-7 ]
  • [ 57625-74-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; for 2h; 2-methyl-2-phenyl-propanol (Intermediate 3) (0.5 kg) and pyridine (268 ml) were charged to a reactor and chilled to 0C. Acetic anhydride (680 gms) was slowly added through a dropper at 10-20C. The mixture was stirred for 2 hours at 10-20C. Ethyl acetate (1.5 ltr) was added and chilled water (2 ltrs) was slowly added through a dropper at 10-20C. The mixture was stirred FOR 4 hr. The ethyl acetate layer was separated and 10% chilled dilute HC1 was added. The ethyl acetate layer was then washed with sodium bicarbonate until a pH of 7 was obtained. The ethyl acetate layer was dried with sodium sulphate and concentrated under vacuum. The resulting oil was distilled under vacuum (15 mm OF HG). at 80-100C.
  • 3
  • ethyl acetate n-hexane [ No CAS ]
  • [ 57625-74-8 ]
  • [ 2173-69-5 ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; sodium hydrogencarbonate; In tetrahydrofuran; water; REFERENCE EXAMPLE 123 STR159 To a suspension of lithium aluminum hydride (1.71 g) in tetrahydrofuran (50 ml) was dropwise added a solution of <strong>[57625-74-8]methyl 2-methyl-2-phenylpropionate</strong> (7.97 g) in tetrahydrofuran (20 ml) under ice cooling and the mixture was stirred at room temperature for 30 minutes. To the reaction solution was dropwise added water and then a saturated aqueous solution of sodium bicarbonate, and the solution was extracted with ether. The ehter layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel (100 g) column chromatography. Elution with a mixture solution of hexane-ethyl acetate (2:1) gave 6.32 9 of 2-methyl-2-phenylpropanol. NMR (CDCl3) delta: 1.32 (6H,s), 1.72(1H,s) 3.61(2H,s,), 7.10-7.61(5H,m)
 

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