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Structure of 69716-04-7

Chemical Structure| 69716-04-7

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Product Details of [ 69716-04-7 ]

CAS No. :69716-04-7
Formula : C10H8O4
M.W : 192.17
SMILES Code : OC(=O)CC1=COC2=C1C=CC(O)=C2
MDL No. :MFCD05273635
InChI Key :ZEMXZWJZCWCPBM-UHFFFAOYSA-N
Pubchem ID :2110915

Safety of [ 69716-04-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 69716-04-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 9
Fraction Csp3 0.1
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 49.78
TPSA ?

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

70.67 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.13
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

1.43
Log Po/w (WLOGP)?

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

1.77
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.

0.53
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

1.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.29

Water Solubility

Log S (ESOL):?

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

-2.28
Solubility 1.02 mg/ml ; 0.0053 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.

-2.52
Solubility 0.581 mg/ml ; 0.00303 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

-2.49
Solubility 0.618 mg/ml ; 0.00321 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

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.

-6.46 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

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

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)

2.38

Application In Synthesis of [ 69716-04-7 ]

* 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 [ 69716-04-7 ]

[ 69716-04-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 69716-04-7 ]
  • [ 78603-91-5 ]
  • [ 1394138-47-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;dichloro [(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex; In methanol; at 35℃; under 7500.75 Torr; for 15h;Autoclave; Example 5Synthesis of [ (3S) -6-hydroxy-2, 3-dihydro-l-benzofuran-3- yl] acetic acid (S) -2-amino-l, 1-diphenylpropan-l-ol salt; [0396] [0397]( 6-Hydroxy-l-benzofuran-3-yl) acetic acid (25 g) ,dichloro[ (+)-l,2-bis( (2R, 5R)-2, 5- diisopropylphosphorano) benzene] ruthenium (II)-N,N- dimethylformamide complex (19.1 mg) and (S) -2-amino-l, .1- diphenylpropan-l-ol (29.5 g) were weighted in an autoclave and substituted with argon. Dehydrated methanol (250 mL) was added and the mixture was purged with hydrogen, pressurized under a hydrogen pressure (1.0 MPa) , and reacted at 35C for 15 hr.The reaction mixture was concentrated under reduced pressure, methanol (109 mL) and N, -dimethylformamide (27 mL) were added, and the mixture was dissolved by heating at 50C. Isopropyl ether (200 mL) was added dropwise at 60C, seed crystal was added, and isopropyl ether (369 mL) was added dropwise. The mixture was cooled to room temperature, stirred for 4 hr and stirred for 1 hr under ice-cooling, and the solid wascollected by filtration. The solid was dried at 60C under reduced pressure to give the title compound (38.98 g) . 99.8%de. XH NMR (500 MHz, DMSO-d6) : delta 0.85-0.92 (m, 1H) , 2.36 (dd,J=14.19 Hz), 2.59 (dd, J=16.24, 2.68 Hz, 1H) , 3.55-3.65 (m, 1H), 4.13 (dd, J=8.83 Hz, 1H) , 4.64 (t, J=8.83 Hz, 1H) , 6.16 (d, J=2.21 Hz, 1H) , 6.23 (dd, J=8.20, 2.21 Hz, 1H) , 6.93-7.00 (m, 1H), 7.09-7.21 (m, 2H) , 7.22-7.35 (m, 4H) , 7.51 (d, J=7.57 Hz, 2H) , 7.63 (dd, J=8.20 Hz, 2H)(high performance liquid chromatography conditions)column: CHIRALPAK AD-H (manufactured by DAICEL CHEMICALINDUSTRIES, LTD.)mobile phase: normal hexane/ethanol/trifluoroacetic acid (volume ratio: 90/10/0.1)flow rate: 1.0 mL/mindetection: UV 220 nmtemperature: 30C
  • 2
  • [ 69716-04-7 ]
  • [ 78603-91-5 ]
  • [ 1394138-48-7 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 60℃; for 1h; Reference Example 3Synthesis of ( 6-hydroxy-l-benzofuran-3-yl) acetic acid (S)-2- amino-1, 1-diphenylpropan-l-ol salt; 0399][0400]( 6-Hydroxy-l-benzofuran-3-yl) acetic acid (25.00 g) and (S) -2-amino-l, 1-diphenylpropan-l-ol (29.57 g) were added to ethyl acetate (175 mL) , and the mixture was dissolved by stirring at 60C. After allowing to cool to room temperature, isopropyl ether (200 mL) was added, and the mixture wasstirred for 1 hr. The solid was collected by filtration, and washed with a mixed solvent (1:1, 100 mL) of ethyl acetate- isopropyl ether. The solid was dried under reduced pressure at 50C to give the title compound (53.81 g) .¾ NMR (500 MHz, DMSO-d6) : delta 0.86 (d, J=5.67 Hz, 3H) , 3.51(br.s., 2H) , 4.06-4.16 (m, 1H) , 6.72 (dd, J=8.35, 2.05 Hz, 1H) , 6.86 (d, J=1.89 Hz, 1H) , 7.10-7.15 (m, 2H) , 7.15-7.37 (m, 5H) , 7.49 (dd, J=8.35, 1.42 Hz, 2H) , 7.58-7.65 (m,3H)
 

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