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Chemical Structure| 25542-62-5 Chemical Structure| 25542-62-5

Structure of Ethyl 6-Bromohexanoate
CAS No.: 25542-62-5

Chemical Structure| 25542-62-5

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Product Details of [ 25542-62-5 ]

CAS No. :25542-62-5
Formula : C8H15BrO2
M.W : 223.11
SMILES Code : CCOC(=O)CCCCCBr
MDL No. :MFCD00000270
InChI Key :DXBULVYHTICWKT-UHFFFAOYSA-N
Pubchem ID :117544

Safety of [ 25542-62-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Class:3
UN#:3272
Packing Group:

Computational Chemistry of [ 25542-62-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.88
Num. rotatable bonds 7
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 49.72
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.8
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

2.53
Log Po/w (WLOGP)?

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

2.5
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.

2.43
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

2.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.56

Water Solubility

Log S (ESOL):?

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

-2.36
Solubility 0.985 mg/ml ; 0.00441 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.

-2.73
Solubility 0.417 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 (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.25
Solubility 0.127 mg/ml ; 0.000569 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.

-5.86 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

0.0
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)

2.34

Application In Synthesis of [ 25542-62-5 ]

* 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 [ 25542-62-5 ]

[ 25542-62-5 ] Synthesis Path-Downstream   1~11

  • 2
  • [ 36822-11-4 ]
  • [ 25542-62-5 ]
  • 6-(6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-hexanoic acid ethyl ester [ No CAS ]
  • 3
  • [ 25542-62-5 ]
  • [ 177429-27-5 ]
  • [ 1133461-67-2 ]
YieldReaction ConditionsOperation in experiment
100% Step 9b: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (Compound 503-16) The title compound 503-16 (6.7 g, 100%) was prepared as a yellowish oil from 502 (4.43 g, 16.3 mmol), ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 307-9 (Example 3): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).
100% Step 11a: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (compound 503-19) The title compound 503-19 (6.7 g, 100%) was prepared as a yellow oil from compound 502 (4.43 g, 16.3 mmol) and ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 503-18 (Example 10): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).
  • 5
  • [ 25542-62-5 ]
  • [ 619-60-3 ]
  • ethyl 6-(4-(dimethylamino)phenoxy)hexanoate [ No CAS ]
  • 6
  • [ 25542-62-5 ]
  • [ 4877-80-9 ]
  • [ 1191091-67-4 ]
  • 7
  • [ 6478-79-1 ]
  • [ 25542-62-5 ]
  • C16H20Cl2N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.75 g To sodium hydride (300 mg) in DMF at 0 C. was added 5,6-dichloro-2-methylbenzoimidazole (500 mg) in one portion. The mixture was stirred at 0 C. for 15 minutes, followed by addition of ethyl 6-bromohexanoate (0.66 mL). The mixture was stirred at 0 C. for another 15 minutes and then at room temperature for 1 hour. The solution was concentrated to dryness under vacuum and the residue was purified by column chromatography on silica gel to give pale brown solid (0.75 g).
  • 8
  • [ 6478-79-1 ]
  • [ 25542-62-5 ]
  • C22H31Cl2N2O4(1+)*Br(1-) [ No CAS ]
  • 9
  • [ 25542-62-5 ]
  • [ 114744-51-3 ]
  • ethyl 6-(7-bromo-3,4-dihydroquinolin-1(2H)-yl)hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18.0h; 7-bromo-l, 2,3,4-tetrahydroquinoline (5. 0 g, 23.6 mmol) was dissolved in DMF (10 mL). Potassium carbonate (6.4 g) and 6-bromohexanoate ethyl ester (10.0 g, 47.2 mmol) were added into the solution. The mixture was heated to 100 C for 18 hours. After the reaction was cooled down, 50 niL of dichloromethane was added and washed with 10 niL of water three times. The organic layer was dried over sodium sulfate and concentrated. It was purified by flash chromatography in silica gel with hexanes-ethyl acetate to afford ethyl 6-(7-bromo-3,4- dihydroquinolin-l(2H)-yl)hexanoates as a clear oil (yield : 70%). H NMR (CDC13): delta 6.79 (d, 1H), 6.64 (d, 2H), 4.15 (t, 2H), 3.29 (t, 2H), 3.21 (t, 2H), 2.32 (t, 2H), 1.92 (m, 2H), 1.72 (m, 2H), 1.65 (m, 2H), 1.43 (m, 2H), 1.31 (t, 3H).
  • 10
  • [ 109-69-3 ]
  • [ 25542-62-5 ]
  • [ 2920-38-9 ]
  • [ 37909-95-8 ]
  • trans-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
  • cis-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
14%Spectr. General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.
  • 11
  • [ 25542-62-5 ]
  • [ 617-05-0 ]
  • ethyl 4-(6-ethoxy-6-oxohexyloxy)-3-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Schlenk technique; A mixture of <strong>[617-05-0]ethyl 4-hydroxy-3-methoxybenzoate</strong> 9 (5.0 g,25.51 mmol), potassium carbonate (10.5 g, 76.5 mmol) and ethyl 6-bromohexanoate (6.8 g, 30.6 mmol) in DMF (20 mL) was stirred overnightat rt. The reaction mixture was filtered and concentrated in vacuum.The residue was dissolved in dichloromethane, and washed withbrine. The organic layer was dried over magnesium sulfate, filtered andconcentrated to yield derivative 10. Yield 8.6 g, 99%; 1H NMR(400 MHz, DMSO-d6) delta 1.18 (t, 3H, J=7.0 Hz), 1.31 (t, 3H,J=7.0 Hz), 1.44-1.40 (m, 2H), 1.63-1.56 (m, 2H), 1.78-1.71 (m, 2H),2.31 (t, 3H, J=7.4 Hz), 3.82 (s, 3H), 4.08-4.00 (m, 4H), 4.28 (q, 2H,J=7.2 Hz), 7.04 (d, 1H, J=8.4 Hz), 7.44 (d, 1H, J=1.8), 7.56 (dd,1H, J1=8.5 Hz, J2=2.0 Hz); 13C NMR (100 MHz, DMSO-d6) delta 172.8,165.4, 152.3, 148.5, 123.0, 121.9, 111.9 (2C), 68.1, 60.3, 59.6, 55.5,33.4, 28.2, 25.0, 24.2, 14.2, 14.0; HR-MS m/z 339.1797 (calcd forC18H27O6 [M+H]+, 339.1802).
 

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