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Chemical Structure| 1591-31-7 Chemical Structure| 1591-31-7

Structure of 1591-31-7

Chemical Structure| 1591-31-7

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Product Details of [ 1591-31-7 ]

CAS No. :1591-31-7
Formula : C12H9I
M.W : 280.10
SMILES Code : C2=C(C1=CC=CC=C1)C=CC(=C2)I
MDL No. :MFCD00019028
InChI Key :NXYICUMSYKIABQ-UHFFFAOYSA-N
Pubchem ID :15322

Safety of [ 1591-31-7 ]

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

Computational Chemistry of [ 1591-31-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 64.6
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.62
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

4.92
Log Po/w (WLOGP)?

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

3.96
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.

4.68
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

4.54
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.14

Water Solubility

Log S (ESOL):?

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

-5.29
Solubility 0.00143 mg/ml ; 0.00000509 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.66
Solubility 0.00617 mg/ml ; 0.000022 mol/l
Class?

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

Moderately 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

-5.86
Solubility 0.000386 mg/ml ; 0.00000138 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

Low
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

Yes
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

Yes
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.

-4.52 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

1.0
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

1.0 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)

2.04

Application In Synthesis of [ 1591-31-7 ]

* 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 [ 1591-31-7 ]

[ 1591-31-7 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 626-44-8 ]
  • [ 1591-31-7 ]
  • [ 6326-64-3 ]
  • [ 135-70-6 ]
  • [ 13476-68-1 ]
  • 2
  • [ 1591-31-7 ]
  • [ 471-25-0 ]
  • [ 32340-38-8 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere; General procedure: Compounds (1b-1o) were prepared according to literature.17 To a mixture of Pd(PPh3)2Cl2 (70 mg, 2 mol%), CuI (38 mg, 4 mol%) and DMF (7 mL) taken in a flask, aryl iodide (5.0 mmol), propiolic acid (414 mg, 6.0 mmol) and diisopropylamine (1.30 g, 12.5 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through Celite bed, the filtrate was washed with cold aqueous KOH solution (1 x 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuum at 40 C, dried to get the arylpropiolic acids.
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 20℃; for 12h; In a reaction vessel, p-iodobiphenyl (10.0 mmol), DBU (3.66 g, 24 mmol, 2.4 equiv), Pd(PPh4)3 (288 mg, 0.26 mmol, 2.5 mol %) was dissolved in 12 ml of DMSO.Solution a was formed, then propynoic acid (840 mg, 12 mmol, 1.2 equiv) was dissolved in 12 ml of DMSO to form solution b, and finally solution b was slowly added dropwise to solution a.The reaction was allowed to stir at room temperature for 12 hours. After the reaction was completed, 25 ml of ethyl acetate was added to the reaction solution.Extract with saturated sodium bicarbonate solution, collect the aqueous layer, and adjust the pH to 2.0 with 1 mol/L hydrochloric acid.Finally, the organic layer was extracted with dichloromethane, the organic phase was separated, and the water was removed with anhydrous sodium sulfate.After drying, the solvent was distilled off under reduced pressure to obtain a crude product, and the crude product was separated by column chromatography to obtain a 3-(1,1'-biphenyl)propiolic acid compound.
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 35℃; for 10h;Inert atmosphere; To a 100 mL of round-bottom flask were added Pd(PPh3)4 (577.8 mg, 5 mol%), aryl iodide (10.0 mmol, 1.0 equiv), DBU (3.040 g, 20 mmol, 2.0 equiv) and DMSO (15 mL). Then the solution of propiolic acid (771 mg, 11 mmol, 1.1 equiv) in DMSO (5 mL) was added dropwise. The round-bottom flask was put into a preheated oil bath (35 C). After stirring for 10 h, the reaction mixture was cooled to room temperature. The reaction mixture was diluted with EtOAc, and extracted with saturated aqueous NaHCO3 solution. The aqueous layer was separated, acidified to pH 2.0 by cold HCl (1N), and extracted with CH2Cl2. The combined organic layers were dried with Na2SO4, filtered, and the solvent was removed under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (PE/EA = 2:1 with HOAc (1%, v/v)) to give 1b-1q.
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  • [ 109-72-8 ]
  • [ 1591-31-7 ]
  • [ 37909-95-8 ]
  • 4
  • [ 2882-15-7 ]
  • [ 1591-31-7 ]
  • 2-(1-([1, 1'-biphenyl]-4-yl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With copper(II) oxide; potassium hydroxide; In N,N-dimethyl-formamide; at 154℃; for 5h;Inert atmosphere; To a solution of 3 (1.5 g, 7.5 mmol), 4-iodo-1, 1'-biphenyl (1.8 g, 8.3 mmol), KOH (0.87 g, 16.5 mmol) and CuO (0.26 g, 3.2 mmol) in 20 mL of DMF. After refluxing at 154 C under N2 protection for 5 h, the solution was poured into 300 mL of HCl (0.5 mol/L) with off white solid precipitation. The solid particles were filtered from water, the solid was then dissolved using EtOAc. The insoluble impurities were filtered from solution and the EtOAc was distillated under reduced pressure. Finally, the brown oil was purified by silica gel chromatography (PE/EA = 5:1, 0.3% HOAc) to generate compound 7b as a yellow powder solid. Yield: 41%, mp: 160-162 C. 1H NMR (400 MHz, DMSO-d6) delta 12.22 (s, 1H), 7.88 (d, J = 8.5 Hz, 2H), 7.82-7.70 (m, 2H), 7.57-7.46 (m, 4H), 7.42 (t, J = 7.4 Hz, 1H), 7.04 (d, J = 2.4 Hz, 1H), 7.01 (d, J = 8.8 Hz, 1H), 6.71 (dd, J = 8.8, 2.4 Hz, 1H), 3.79 (s, 3H), 3.68 (s, 2H), 2.26 (s, 3H).
  • 5
  • [ 1591-31-7 ]
  • [ 32340-38-8 ]
  • 6
  • [ 1591-31-7 ]
  • [ 22651-87-2 ]
  • [ 3842-58-8 ]
  • 7
  • [ 64-18-6 ]
  • [ 1591-31-7 ]
  • [ 106-94-5 ]
  • [ 13211-01-3 ]
  • 8
  • [ 1591-31-7 ]
  • [ 14984-26-0 ]
  • 5-([1,1'-biphenyl]-4-yl)-2-phenylbenzo[4,5]imidazo[1,2-a]quinoline [ No CAS ]
 

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