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Chemical Structure| 117-99-7 Chemical Structure| 117-99-7

Structure of 117-99-7

Chemical Structure| 117-99-7

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Product Citations

Product Citations

Phan, Son NT ; Teets, Thomas S ;

Abstract: Phosphorescent platinum(II) complexes often have low photoluminescence quantum yields (ΦPL) due to the less effective spin−orbit coupling (SOC) in square-planar geometries, leading to relatively small radiative rate constants (kr). In this work, seven new red-emitting heteroleptic cyclometalated Pt(II) complexes are described, with the goal of investigating ancillary ligands that promote fast kr values. The heteroleptic fourcoordinate complexes include 1-phenylisoquinoline as the cyclometalating ligand, paired with an anionic chelating ancillary ligand with either N^N, O^O, or mixed N^O coordination. More specifically, the ancillary ligands all contain anionic pyrrolide or phenoxide rings, paired with imine, carbonyl, pyridyl, or imidazolyl neutral donors. The seven compounds are structurally characterized by multinuclear NMR and six of the seven by single-crystal X-ray diffraction. A comprehensive study of photophysical properties shows that the compounds all exhibit red phosphorescence, some with a clear vibronic structure indicative of the substantial 3 (π → π*) character in the emissive excited state, involving the cyclometalating ligand, while others exhibit a photoluminescence profile suggestive of pronounced charge-transfer character in the triplet state. When measured in poly(methyl methacrylate) films, the highest kr achieved is 1.2 × 105 s −1, with photoluminescence quantum yields ranging from 0.14 to 0.38.

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Product Details of [ 117-99-7 ]

CAS No. :117-99-7
Formula : C13H10O2
M.W : 198.22
SMILES Code : O=C(C1=CC=CC=C1O)C2=CC=CC=C2
MDL No. :MFCD00002216
InChI Key :HJIAMFHSAAEUKR-UHFFFAOYSA-N
Pubchem ID :8348

Safety of [ 117-99-7 ]

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

Computational Chemistry of [ 117-99-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 58.34
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.19
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

3.52
Log Po/w (WLOGP)?

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

2.62
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.

2.34
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

2.92
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.72

Water Solubility

Log S (ESOL):?

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

-3.75
Solubility 0.0355 mg/ml ; 0.000179 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.

-3.99
Solubility 0.0204 mg/ml ; 0.000103 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

-4.29
Solubility 0.0101 mg/ml ; 0.0000511 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

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.

-5.01 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.

0.55

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)

1.4

Application In Synthesis of [ 117-99-7 ]

* 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 [ 117-99-7 ]

[ 117-99-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 117-99-7 ]
  • [ 14019-62-6 ]
  • isopropyl (E)-N-[(2-Hydroxyphenyl)(phenyl)methylene]glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; In methanol; at 20℃; for 24h; General procedure: The appropriate glycine ester hydrochloride (17.7 mol) and Et3N (2.2mL, 17.7 mol) were added to a solution of 2-hydroxybenzophenone (1; 3.5 g, 17.7 mmol) in MeOH (10 mL), and the solution was stirred atr.t. for 24 h. The mixture was then concentrated in vacuo and acetone was added. The precipitated Et3N·HCl was collected by filtration and washed with acetone. The filtrate was evaporated to dryness, and the product was crystallized from MeOH (for 2a,b) or from DCM-hexanes (for 2c). Important The recovered 2-hydroxybenzophenone (1) could be repeatedly used to prepare the initial product 2 (for recovery method, see below).
 

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