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Structure of 3401-47-6

Chemical Structure| 3401-47-6

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Product Details of [ 3401-47-6 ]

CAS No. :3401-47-6
Formula : C11H9BrO
M.W : 237.09
SMILES Code : COC1=C(Br)C2=C(C=CC=C2)C=C1
MDL No. :MFCD00055374
InChI Key :XNIGURFWNPLWJM-UHFFFAOYSA-N
Pubchem ID :72860

Safety of [ 3401-47-6 ]

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

Computational Chemistry of [ 3401-47-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 10
Fraction Csp3 0.09
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 58.14
TPSA ?

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

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.57
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

3.83
Log Po/w (WLOGP)?

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

3.61
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.

3.52
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

3.63
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.43

Water Solubility

Log S (ESOL):?

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

-4.23
Solubility 0.0141 mg/ml ; 0.0000594 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.

-3.72
Solubility 0.0452 mg/ml ; 0.000191 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

-5.06
Solubility 0.00207 mg/ml ; 0.00000873 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

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.

-5.03 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)

1.34

Application In Synthesis of [ 3401-47-6 ]

* 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 [ 3401-47-6 ]

[ 3401-47-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 13716-10-4 ]
  • [ 3401-47-6 ]
  • [ 36321-73-0 ]
  • 1-(2-di-tert-butylphosphino-3,4,5,6-tetramethylphenyl)-2-methoxynaphthalene [ No CAS ]
  • 2
  • [ 3401-47-6 ]
  • [ 219834-96-5 ]
  • (S)-2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene [ No CAS ]
  • 2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene [ No CAS ]
  • 5
  • [ 3401-47-6 ]
  • [ 133730-34-4 ]
  • 1-(2,4-dimethoxyphenyl)-2-methoxynaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium phosphate monohydrate; dicyclohexyl(2,6-dimethoxy-3-(2-methoxynaphthalen-1-yl)phenyl)phosphane; palladium diacetate; In tetrahydrofuran; water; at 35℃; for 4h;Inert atmosphere; A flame dried 250 mL 3-neck round bottomed flask containing a magnetic stir bar was charged with 2-methoxybromonaphthalene (3.56 g, 15.0 mmol), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (5.46 g, 30.0 mmol), and tribasic potassium phosphate monohydrate (8.64 g, 37.5 mmol) under a flow of argon. The vessel was evacuated and backfilled with argon 3 times. A solution of Pd(OAc) (33.7 mg, 0.15 mmol) and L1 (0.104 g, 0.225 mmol) in THF (1.5 mL) was added via syringe to the vessel followed by THF (1.5 mL) and a degassed solution of 2 wt % TPGS-750-M in water (27 mL). The vessel was placed in an oil bath at 35 C. and stirred vigorously. GC/MS and TLC monitoring showed complete consumption of the bromide after 4 h. The crude mixture was transferred to a separatory funnel and extracted with EtOAc (3*20 mL). The combined organic phases were dried over anhydrous Na2SO4 followed by solvent removal in vacuo. The mixture was chromatographed on silica gel eluting with 1:4 diethyl ether:hexanes (Rf=0.20 1:4 diethyl ether:hexanes). The pure product was collected. The impure fractions were collected separately, concentrated and the product was recrystallized from a 1:1 mixture of EtOAc:hexanes yielding an off-white/gray powder (combined 1.54 g, 70%). 1H NMR (500 MHz, chloroform-d) δ 7.87 (d, J=9.0 Hz, 1H), 7.83-7.79 (m, 1H), 7.44-7.40 (m, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.34-7.29 (m, 2H), 7.13 (d, J=7.8 Hz, 1H), 6.67-6.63 (m, 2H), 3.90 (s, 3H), 3.85 (s, 3H), 3.68 (s, 3H). 13C NMR (101 MHz, chloroform-d) δ 160.38, 158.63, 154.47, 133.97, 132.63, 129.04, 128.90, 127.80, 126.03, 125.31, 123.33, 121.77, 117.67, 114.10, 104.40, 99.03, 56.93, 55.66, 55.34.
  • 6
  • [ 3401-47-6 ]
  • [ 66996-59-6 ]
  • 7
  • [ 3401-47-6 ]
  • [ 112734-22-2 ]
  • C18H15BrFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); SPhos; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 130 - 140℃;Inert atmosphere; 1000ml three-necked bottle, in the case of nitrogen 50.0 g of starting material A (211 mmol), 50.7 g of sodium t-butoxide (527 mmol), 0.97 g of Pd2(dba)3 (1.05 mmol),0.87g of S-phos (2.04mmol) and 150ml of xylene, heated to 130 ° C ~ 140 ° C, temperature control 130 ° C ~ 140 ° C slowly added 43.0g of raw material B (211mmol) and 400ml of xylene mixed solution, add dropwise, Keep warm for 15h, TLC detects the completion of the reaction; cools to room temperature, Filter and filter the cake with xylene. The column liquid was steamed to a non-fraction, and the crude yellow solid was purified with toluene. Drying to obtain 53.2 g of intermediate A, yield: 70percent,
 

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