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Chemical Structure| 7287-82-3 Chemical Structure| 7287-82-3

Structure of 7287-82-3

Chemical Structure| 7287-82-3

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Product Details of [ 7287-82-3 ]

CAS No. :7287-82-3
Formula : C9H12O
M.W : 136.19
SMILES Code : CC(O)C1=CC=CC=C1C
MDL No. :MFCD00046632
Boiling Point : No data available

Safety of [ 7287-82-3 ]

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

Computational Chemistry of [ 7287-82-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 42.34
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.

2.11
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

1.77
Log Po/w (WLOGP)?

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

1.72
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.

2.19
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

2.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.02

Water Solubility

Log S (ESOL):?

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

-2.18
Solubility 0.905 mg/ml ; 0.00665 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.

-1.81
Solubility 2.1 mg/ml ; 0.0154 mol/l
Class?

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

Very 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

-2.61
Solubility 0.331 mg/ml ; 0.00243 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.

-5.87 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)

1.16

Application In Synthesis of [ 7287-82-3 ]

* 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 [ 7287-82-3 ]

[ 7287-82-3 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
With 1H-imidazole; [bis(acetoxy)iodo]benzene; C84H72ClFeN4O12S4(4-)*4Na(1+); In methanol; water; for 1h;Inert atmosphere; General procedure: Iron porphyrin complex 1 (1.6 mg, 1 mumol) and imidazole (0.68 mg, 10 mumol) was placed in a test tube under argon. Then, 0.8 ml of distilled methanol and 0.2 ml H2O were added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2, (32 mg, 100 mumol) in 0.2 ml methanol was added over a period of 45 mn. After 1 h, the mixture was analysed by GC for oxidation yield, 46%, based on oxidant, and for epoxide enantiomeric excess, 75%. Polarimetric measurement of the oxidation product determined that (S)-(-)-1-phenylethanol was formed in excess. In addition to expected phenylethanol, acetophenone was also observed.The reaction and analysis of the other susbtrates in Table 1 were carried out in a manner identical with that used for ethylbenzene oxidation except for indane and tetrahydronaphtalene. In the latter case, enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol=95/5; flow rate=0.5 ml min-1; wavelength=220 nm.
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YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ferrocenium(III) tetrafluoroborate; ethylbenzene dehydrogenase; In water; tert-butyl alcohol; at 30℃;Enzymatic reaction; General procedure: 2.1. Sample preparation Ethylbenzene dehydrogenase was purified from ethylbenzene-grown A. aromaticum cells as previously described [11,23]. The enzyme assays were routinely conducted at an optimum pH of 7.5 at 30 C in 20 ml of 100 mM Tris/HCl containing 200 muM ferrocenium (III) tetrafluoroborate and ethylbenzene dehydrogenase (100-300 mul of app. 1 mg/ml protein solution). The reactions were initiated by adding 100 mul of a stock solution of the respective substrate in tert-butanol (a list of substrates, their purities and producers is available in the Supporting Information). After an overnight incubation, the reaction mixtures were extracted from the water phase by solid-phase extraction using either C18 Polar Plus (J.T. Baker from Avantor Performance Materials, US) or polystyrene/divinylbenzene (PS/DVB) copolymers solid phase extraction (SPE) columns (Strata-X from Phenomenex, US or the equivalent Chromabond HR-X from Macherey-Nagel, Germany), which were eluted with 0.5 ml of isopropanol. The only exception to the procedure was the 2-ethyl-1H-pyrrole reaction mixtures (22). Due to the high polarity of the product derived from this compound, we were unable to concentrate the sample and exchange the solvent by SPE. Therefore, the enzyme was precipitated by the addition of 50% methanol, and it was removed by centrifugation. The supernatant was directly analyzed by non-chiral reversed-phase (RP)-LC.
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  • 7
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  • [ 42070-90-6 ]
  • [ 577-16-2 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene; chloro(5,10,15,20-tetrakis-(10-nitro-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-dimethanoanthracen-9-yl)porphyrin) iron(III); In methanol; dichloromethane; water; for 2h;Inert atmosphere; General procedure: Iron porphyrin complex 5 (1.2 mg 1 mumol) and imidazole (0.34 mg, 10 mumol) were placed in a test tube under argon. Then, 1 ml of distilled CH2Cl2/MeOH/H2O mixture (0.5:0.4:0.1) was added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2 (32 mg, 100 mumol) in 0.1 ml CH2Cl2 was added over a period of 1 h with a syringe-pump. After the addition of all the PhI(OAc)2, the reaction mixture was allowed to stir for an additional 1 h. The mixture was analyzed by GC for oxidation yield based on oxidant, 41 %, alcohol/ketone ratio, 83:17, and alcohol enantiomeric excess, 68 % (conditions used: 80 C (1 min), 1 C min-1 80-120 C, 2.5 C min-1 120-180 C). Polarimetric measurement of the oxidation product determined that (R)-(+)-1-phenyl ethanol was formed in excess. The reaction and analysis of the other substrates and catalysts in Table 3 were carried out in an identical manner with that used for ethylbenzene oxidation. Except for indane, the enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol 95:5; flow rate: 0.5 ml min-1, detection: 220nm.
  • 8
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  • [ 767-90-8 ]
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  • 10
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YieldReaction ConditionsOperation in experiment
93% With C20H26B10Cl2FeN6; dihydrogen peroxide; In methanol; at 20℃; for 8h; Dissolve 2-methylethylbenzene (1.0 mmol), iron complex 1 (0.02 mmol) and H2O2 (1.5 mmol) in 2 mL of methanol and react at room temperature for 8 hours.After the reaction, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding product C9H12O was obtained (93% yield).
 

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