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Chemical Structure| 50390-49-3 Chemical Structure| 50390-49-3

Structure of 50390-49-3

Chemical Structure| 50390-49-3

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Product Details of [ 50390-49-3 ]

CAS No. :50390-49-3
Formula : C12H16O
M.W : 176.26
SMILES Code : CC(C)(C)C(C1=CC=CC(C)=C1)=O
MDL No. :MFCD03841163
InChI Key :FIRWPECOXVVSRF-UHFFFAOYSA-N
Pubchem ID :14250269

Safety of [ 50390-49-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 50390-49-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.42
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 55.76
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.5
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

3.55
Log Po/w (WLOGP)?

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

3.22
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.

2.97
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

3.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.13

Water Solubility

Log S (ESOL):?

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

-3.38
Solubility 0.0737 mg/ml ; 0.000418 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.

-3.59
Solubility 0.0449 mg/ml ; 0.000255 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

-3.94
Solubility 0.0202 mg/ml ; 0.000115 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

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

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.

-4.85 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<2.0
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)

1.09

Application In Synthesis of [ 50390-49-3 ]

* 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 [ 50390-49-3 ]

[ 50390-49-3 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 100485-55-0 ]
  • [ 50390-49-3 ]
  • 4
  • [ 3282-30-2 ]
  • [ 937-01-9 ]
  • [ 98-51-1 ]
  • [ 30314-44-4 ]
  • [ 1075-38-3 ]
  • [ 50390-49-3 ]
  • 6
  • [ 50390-49-3 ]
  • [ 120136-04-1 ]
  • 7
  • [ 50390-49-3 ]
  • [ 120136-20-1 ]
  • 8
  • [ 620-22-4 ]
  • [ 50390-49-3 ]
  • 9
  • [ 3282-30-2 ]
  • [ 68971-88-0 ]
  • [ 50390-49-3 ]
YieldReaction ConditionsOperation in experiment
55% With indium; In neat (no solvent); at 60℃; for 22h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 11
  • [ 50390-49-3 ]
  • [ 1779-49-3 ]
  • 1-(3,3-dimethylbut-1-en-2-yl)-3-methylbenzene [ No CAS ]
  • 12
  • [ 50390-49-3 ]
  • 1-(3,3-dimethylbutan-2-yl)-3-methylbenzene [ No CAS ]
  • (S)-1-(3,3-dimethylbutan-2-yl)-3-methylbenzene [ No CAS ]
  • 13
  • [ 50390-49-3 ]
  • (S)-1-(3,3-dimethylbutan-2-yl)-3-methylbenzene [ No CAS ]
  • 14
  • [ 50390-49-3 ]
  • [ 56530-39-3 ]
  • C20H19NO3 [ No CAS ]
  • 15
  • [ 1112-54-5 ]
  • [ 50390-49-3 ]
  • C20H34OSi [ No CAS ]
  • 16
  • [ 1631-26-1 ]
  • [ 50390-49-3 ]
  • 1-benzyl-3-(4-methyl-2-pivaloylphenyl)pyrrolidine-2,5-dione [ No CAS ]
  • 17
  • [ 50390-49-3 ]
  • [ 107-05-1 ]
  • C15H20O [ No CAS ]
  • 1-(2-allyl-5-methylphenyl)-2,2-dimethylpropan-1-one [ No CAS ]
  • 18
  • [ 50390-49-3 ]
  • 2,2-dimethyl-1-(m-tolyl)propan-1-ol [ No CAS ]
  • 2,2-dimethyl-1-(m-tolyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With borane-ammonia complex; C68H65O4PSi2; water; In carbon disulfide; at 20℃; for 12h;Sealed tube; General procedure: To a sealed tube (15 mL) were added chiral phosphoric acid 1a (0.0021g, 0.002 mmol), ketone 1e (0.0769 g, 0.4 mmol), and carbon disulfide (2.0 mL). Then water (7.9 muL, 0.44 mmol) and ammonia borane (0.0136 g, 0.44 mmol) were added, and the resulting mixture was stirred at room temperature for 12 h. The mixture was purified by flash chromatography on silica gel using petroleum ether/ ethyl acetate (50/1) to petroleum ether/ethyl acetate (10/1) as the eluent to give the desired product 4e as a colorless oil (0.0716 g, 92% yield, 74% ee).
 

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Technical Information

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