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Chemical Structure| 59662-46-3 Chemical Structure| 59662-46-3

Structure of 59662-46-3

Chemical Structure| 59662-46-3

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Product Details of [ 59662-46-3 ]

CAS No. :59662-46-3
Formula : C17H18O2
M.W : 254.32
SMILES Code : CCCCC1=CC=C(C=C1)C1=CC=C(C=C1)C(O)=O
MDL No. :MFCD00222812
Boiling Point : No data available
InChI Key :BVBTVBVHIQDKKW-UHFFFAOYSA-N
Pubchem ID :2757304

Safety of [ 59662-46-3 ]

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

Computational Chemistry of [ 59662-46-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.24
Num. rotatable bonds 5
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 78.22
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.

2.76
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

5.6
Log Po/w (WLOGP)?

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

4.39
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.

4.16
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

4.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.29

Water Solubility

Log S (ESOL):?

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

-5.08
Solubility 0.0021 mg/ml ; 0.00000828 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.

-6.15
Solubility 0.000182 mg/ml ; 0.000000715 mol/l
Class?

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

Poorly 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

-5.89
Solubility 0.000325 mg/ml ; 0.00000128 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

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

Yes
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.

-3.88 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.

0.56

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<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)

1.8

Application In Synthesis of [ 59662-46-3 ]

* 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 [ 59662-46-3 ]

[ 59662-46-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 14938-35-3 ]
  • [ 59662-46-3 ]
  • [ 61733-14-0 ]
  • 2
  • [ 52709-83-8 ]
  • [ 59662-46-3 ]
  • 3
  • [ 59662-46-3 ]
  • [ 150-76-5 ]
  • [ 61733-31-1 ]
  • 4
  • [ 59662-46-3 ]
  • [ 89111-63-7 ]
  • 4-cis-(4-trans-butylcyclohexyl)cyclohexanecarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
There are prepared analogously: 4-(4-ethylphenyl)-benzoic acid, 4-(4-n-propylphenyl)-benzoic acid, 4-(4-n-butylphenyl)-benzoic acid, 4-(4-n-hexylphenyl)-benzoic acid,
  • 6
  • [ 350792-80-2 ]
  • Wang-resin-CH2O(p-C6H4)-CH2OC(O)-p-C6H4)-I [ No CAS ]
  • [ 59662-46-3 ]
  • 7
  • [ 350792-89-1 ]
  • Wang-resin-CH2O-(p-C6H4)-CH2OC(O)(p-C6H4)-I [ No CAS ]
  • [ 59662-46-3 ]
  • 8
  • [ 350792-89-1 ]
  • Wang resin-tethered 4-iodobenzoic acid [ No CAS ]
  • [ 59662-46-3 ]
  • 9
  • [ 155408-84-7 ]
  • Wang resin-tethered 4-iodobenzoic acid [ No CAS ]
  • [ 59662-46-3 ]
  • 11
  • [ 350792-82-4 ]
  • [ 59662-46-3 ]
  • 12
  • [ 1451206-56-6 ]
  • [ 59662-46-3 ]
YieldReaction ConditionsOperation in experiment
71.1% With water; sodium hydroxide; In tetrahydrofuran;Reflux; [00269] General Method 13: The synthesis of a biaryl or aryl-heteroaryl carboxylic acid from l-bromo-4-butylbenzene and an aryl- or heteroaryl boronic acid. An illustration of this method is depicted for 4-(4-butylphenyl)benzoic acid. [00271] A mixture of methyl 4-(4-butylphenyl)benzoate (89.0 g, 0.332 mol), NaOH (26.6 g, 0.664 mol) in THF/H20 (500 mL/100 mL) was heated to reflux overnight. After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH -3-4 with 2 N HC1 solution. The resulting mixture was filtered and the cake was washed with water, dried to give 4-(4-butylphenyl)benzoic acid (60.0 g, yield: 71.1%), as a white solid. (ESI) m/z 255.0 (M + H)+.
71.1% With water; sodium hydroxide; In tetrahydrofuran; A mixture of methyl 4?-butyl-[1,1?-biphenylj-4-carboxylate (89.0 g, 0.332mol), NaOH (26.6 g, 0.664 mol) in THF/H20 (500 mL/100 mL) was heated to reflux overnight.After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH=34 with 2 N HC1 solution. The resulting mixture was filtered and the cake was washed with water, and dried to give 4?-butyl-[1,1?-biphenylj-4-carboxylic acid (60.0 g, 71.1%) as a white solid.
71.1% With sodium hydroxide; In tetrahydrofuran; water;Reflux; A mixture of methyl 4?-butyl-[1,1?-biphenylj-4-carboxylate (89.0 g, 0.332 mol), NaOH (26.6 g, 0.664 mol) in THF/H20 (500 mL/100 mL) was heated to reflux overnight. After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH=34 with 2 N HC1 solution. The resulting mixture was filtered and the cake was washed with water, and dried to give 4?-butyl- [1,1 ?-biphenylj -4-carboxylic acid (60.0 g, 71.1%) as a white solid.
With hydrogenchloride; In water; A mixture of methyl 4-(4-butylphenyl)benzoate (89.0 g, 0.332 mol), NaOH (26.6 g, 0.664 mol) in THF/H2O (500 mL/100 mL) was heated to reflux overnight. After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH ?3-4 with 2 N HCl solution. The resulting mixture was filtered and the cake was washed with water, dried to give 4-(4-butylphenyl)benzoic acid (60.0 g, yield: 71.1%), as a white solid. (ESI) m/z 255.0 (M+H)+.

  • 14
  • [ 59662-46-3 ]
  • (S)-5-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-methoxy-6-oxohexan-1-aminium chloride [ No CAS ]
  • [ 1451207-52-5 ]
YieldReaction ConditionsOperation in experiment
54.4% With sodium hydrogencarbonate; HATU; In tetrahydrofuran; N,N-dimethyl-formamide; at 25℃; for 5h; [00351] To a solution of Compound 278A1 (1.00 g, 2.39 mmol), 4-(4- butylphenyl)benzoic acid (0.728 g, 2.89 mmol) and NaHC03 (0.742 g, 8.84 mmol) in dry THF (30 mL) and DMF (30 mL) was added HATU (1.09 g, 2.89 mmol). The mixture was stirred at 25 C until LCMS indicated the reaction was finished (5 hrs). THF was evaporated and the mixture was poured into water (100 mL) and extracted with DCM (80 mL x 2). The combined organic layers were evaporated and purified by silica-gel column chromatography to give Compound 278A2 (800 mg, yield: 54.4 %).
  • 15
  • C45H61N6O9Pol [ No CAS ]
  • [ 59662-46-3 ]
  • C62H77N6O10Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
[00243] A mixture of <strong>[59662-46-3]4-(4-butylphenyl)benzoic acid</strong> (1.5 eq), HCTU (1.5 eq), HOBT (1.5 eq) and DIPEA (1.5 eq) in dry DMF (6 - 8 mL/eq) was stirred at 20C for 30 min. Then the above mixture was added to Compound 129D2 (1 eq) and shaken at 20 C for 1.5 hrs. After LCMS showed the reaction was completed, the mixture was filtered and the residue was washed with DMF (3 x 10 mL/mmol), DCM (3 x 10 mL/mmol), THF (3 x 10 mL/mmol) and petroleum ether (3 x 10 mL/mmol) to give Compound 129E1.
  • 16
  • [ 59662-46-3 ]
  • [ 1451207-53-6 ]
  • 17
  • [ 59662-46-3 ]
  • [ 1451207-54-7 ]
  • 18
  • [ 59662-46-3 ]
  • [ 287115-11-1 ]
  • C31H32O7 [ No CAS ]
  • 19
  • [ 59662-46-3 ]
  • 4'-butylbiphenyl-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20℃; General procedure: was prepared by stirring amixture of 1a (1.16 g, 5 mmol),SOCl2 (0.59 g, 5 mmol), and several drops of DMF in toluene (30 mL) at ambient temperaturefor 5 hr. The solvent was removed under vacuum. A brown liquid (2a) was obtainedand used to next step without further purifying.
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20℃; for 5h; General procedure: 2a was prepared by heating and stirring a mixture of 4-ethyl(4-trans-cyclohexyl)benzoicacid(1a) (1.16 g, 5 mmol) and SOCl2 (0.60 g, 5 mmol) and several drops of DMF in toluene (25 mL) at ambient temperature for 5 hr. The solvent was then removed under vaccum condition. A brown liquid (2a) was obtained and used to next step without further purifying.
  • 20
  • [ 59662-46-3 ]
  • 4-4-(4-(4-(4-n-butylphenyl)benzoyloxy)phenyldiazenyl)benzaldehyde [ No CAS ]
  • 21
  • [ 59662-46-3 ]
  • 4-(4-(4-(4-n-butylphenyl)benzoyloxy)phenyldiazenyl)benzoic acid [ No CAS ]
  • 22
  • [ 59662-46-3 ]
  • 4-(4-(4-(4-n-butylphenyl)benzoyloxy)phenyldiazenyl)benzoic acid [ No CAS ]
  • 23
  • [ 59662-46-3 ]
  • [ 115914-43-7 ]
  • nonane-1,9-diylbis(4,1-phenylene) bis(4'-butyl-[1,1'-biphenyl]-4-carboxylate) [ No CAS ]
  • 24
  • [ 59662-46-3 ]
  • C51H65N9O7 [ No CAS ]
  • 25
  • [ 59662-46-3 ]
  • C63H85N7O14 [ No CAS ]
  • 26
  • [ 59662-46-3 ]
  • C64H87N7O14 [ No CAS ]
  • 28
  • [ 59662-46-3 ]
  • C45H53N5O8 [ No CAS ]
  • 30
  • [ 59662-46-3 ]
  • C66H89N9O13 [ No CAS ]
  • 31
  • [ 1334236-89-3 ]
  • [ 59662-46-3 ]
  • C52H65N5O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.6% The coupling of an acid chloride to an amine is is described for this example.A mixture of <strong>[59662-46-3]4-(4-butylphenyl)benzoic acid</strong> (200 mg, 0.79 mmol) in thionyl chloride (5.0 mL)was stirred at 60 C for 16 h. The solution was concentrated and dissolved in dichloromethane(2 mL). To the solution of Compound 119-B (500 mg, 0.73 mmol) and triethylamine (74 mg,0.73 mmol) in dichloromethane (15 mL) was added the above solution of 4-(4-butylphenyl)benzoyl chloride in dichloromethane. The reaction mixture was stirred at 25 C for3 h. The reaction was concentrated to dryness and the residue was purified by flash columnchromatography (eluted with 5% dichloromethane in methanol). The desired fractions were concentrated to afford Compound 119-C (650 mg, 96.6% yield) as a white solid. LCMS (5- 95AB/1.5 mm): tR = 0.95 1 mi [M + Hj 921.4. Alternatively, this coupling reaction can be performed using 4?-butyl-[1,1?-biphenylj-4-carboxylic acid using General Method HATUconditions in Example 4.
96.6% The coupling of an acid chloride to an amine is General Method Acid Chlorideand is described for this example. A mixture of <strong>[59662-46-3]4-(4-butylphenyl)benzoic acid</strong> (200 mg, 0.79mmol) in thionyl chloride (5.0 mL) was stirred at 60 C for 16 h. The solution was concentrated and dissolved in dichloromethane (2 mL). To the solution of Compound 331-B (500 mg, 0.73 mmol) and triethylamine (74 mg, 0.73 mmol) in dichloromethane (15 mL) was added the above solution of 4-(4-butylphenyl)benzoyl chloride in dichloromethane. The reaction mixture wasstirred at 25 C for 3 h. LCMS showed that all of start material was consumed completely. TLC (10% dichloromethane in methanol, Rf = 0.4). The reaction was concentrated to dryness and the residue was purified by flash column chromatography (eluted with 5% dichloromethane in methanol). The desired fractions were concentrated to afford Compound 331-C (650 mg, 0.71 mmol, 96.6% yield) as a white solid. LCMS (5-95AB/1.5 mm): tR = 0.95 1 mi [M + Hj 921.4.Alternatively, this coupling reaction can be performed using 4?-butyl-[1,1?-biphenylj-4- carboxylic acid using General Method HATU conditions in Example 4.
  • 32
  • [ 59662-46-3 ]
  • C49H59N5O10 [ No CAS ]
  • 33
  • [ 59662-46-3 ]
  • (x)CH2O2*C50H63N9O7 [ No CAS ]
  • 34
  • [ 59662-46-3 ]
  • C65H87N9O13 [ No CAS ]
  • 35
  • [ 59662-46-3 ]
  • C52H65N5O10 [ No CAS ]
 

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