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Chemical Structure| 145240-28-4 Chemical Structure| 145240-28-4

Structure of 145240-28-4

Chemical Structure| 145240-28-4

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Product Details of [ 145240-28-4 ]

CAS No. :145240-28-4
Formula : C10H15BO2
M.W : 178.04
SMILES Code : C(CCC)C1=CC=C(C=C1)B(O)O
MDL No. :MFCD02093926
InChI Key :UGZUUTHZEATQAM-UHFFFAOYSA-N
Pubchem ID :4100860

Safety of [ 145240-28-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 145240-28-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 55.65
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

2.71
Log Po/w (WLOGP)?

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

0.71
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.

1.56
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

0.72
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.14

Water Solubility

Log S (ESOL):?

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

-2.73
Solubility 0.333 mg/ml ; 0.00187 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.

-3.21
Solubility 0.109 mg/ml ; 0.000612 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

-2.89
Solubility 0.231 mg/ml ; 0.0013 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.

-5.46 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.

0.55

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)

1.65

Application In Synthesis of [ 145240-28-4 ]

* 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 [ 145240-28-4 ]

[ 145240-28-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1445-39-2 ]
  • [ 145240-28-4 ]
  • [ 1361537-67-8 ]
  • 2
  • [ 591-50-4 ]
  • [ 145240-28-4 ]
  • [ 37909-95-8 ]
YieldReaction ConditionsOperation in experiment
34% In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.
  • 3
  • [ 74137-36-3 ]
  • [ 145240-28-4 ]
  • 4,4''-dibutyl-5'-methoxy-1,1':3',1''-terphenyl [ No CAS ]
  • 4
  • [ 591-50-4 ]
  • [ 2525-42-0 ]
  • [ 18162-48-6 ]
  • [ 145240-28-4 ]
  • [ 37909-95-8 ]
  • [(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
26%; 64% In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.
  • 5
  • C54H45O3P2PdS(1+)*BF4(1-) [ No CAS ]
  • [ 18162-48-6 ]
  • [ 145240-28-4 ]
  • [ 37909-95-8 ]
  • [(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
15%; 80% In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added complex 8 (51 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol, 2 eq.), boronic acids 3a (9 mg, 0.05mmol, 1 eq.) and THF (3 mL), then phenyl iodide 2a (10 mg, 0.05 mmol, 1 eq.) were also charged into the reaction mixture. The joint position between the vial and cap was sealed with black electric tape to save the nitrogen in the vial and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13 hours on the IKA electric stirring machine. After 15 hours, imidazole (17 mg, 0.25 mmol, 5 eq.) and TBSCl (22 mg, 0.15 mmol, 3 eq.) were added into the vial under air and stirred for another 2 hours at room temperature, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the formation of TBS protected allyl alcohol 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a (7 mg, 80%). The spectrum was same as above. The biphenyl product 4aa is also formed with about 1.6 mg (15% yield). There is no reaction occur without the presence of phenyl iodide, which was confirmed by the analysis of 31P NMR of crude reaction mixture.
 

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