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Chemical Structure| 28785-06-0

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Product Details of [ 28785-06-0 ]

CAS No. :28785-06-0
Formula : C10H12O
M.W : 148.20
SMILES Code : O=CC1=CC=C(CCC)C=C1
MDL No. :MFCD00041870
InChI Key :MAUCRURSQMOFGV-UHFFFAOYSA-N
Pubchem ID :120047

Safety of [ 28785-06-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 28785-06-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 3
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 46.41
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.08
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

2.54
Log Po/w (WLOGP)?

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

2.45
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.

2.4
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

3.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.52

Water Solubility

Log S (ESOL):?

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

-2.56
Solubility 0.404 mg/ml ; 0.00272 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.

-2.55
Solubility 0.422 mg/ml ; 0.00285 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

-3.52
Solubility 0.0446 mg/ml ; 0.000301 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

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

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.

-5.4 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

2.0
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)

1.0

Application In Synthesis of [ 28785-06-0 ]

* 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 [ 28785-06-0 ]

[ 28785-06-0 ] Synthesis Path-Downstream   1~35

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  • 8
  • [ 79-24-3 ]
  • [ 28785-06-0 ]
  • 1-((E)-2-Nitro-propenyl)-4-propyl-benzene [ No CAS ]
  • 9
  • [ 4106-66-5 ]
  • [ 28785-06-0 ]
  • Dibenzofuran-3-yl-[1-(4-propyl-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]
  • 10
  • [ 79-37-8 ]
  • [ 103-65-1 ]
  • [ 28785-06-0 ]
  • 11
  • [ 141-82-2 ]
  • [ 28785-06-0 ]
  • [ 62718-61-0 ]
YieldReaction ConditionsOperation in experiment
In pyridine; at 80℃; for 2h; A 125 mL Ehrlenmayer flask equipped with a magnetic stirrer bar was charged with 7.76 g (47.8 mmol) of <strong>[28785-06-0]4-n-propylbenzaldehyde</strong>, 5.28 g (50.7 mmol) of malonic acid and 2.2 mL (2.2g, 27.2 mmol) of pyridine. The slurry was heated to 800C, at which temperature a clear yellow solution formed. After stirring for 2 hr, the reaction mixture was cooled to 25°C. The resulting solid was isolated by filtration, rinsing with water (2 X 30 mL) and 2: 1 methyl t-butyl ether (MTBE)/hexanes (2 X 30 mL). A total of 3.1 g of 4-n-Propylcinnamic acid was isolated.A 500 mL Parr shaker reaction vessel was charged with 3.10 g (15.2 mmol) of 4- n-Propylcinnamic acid, 20 mL of ethyl acetate and 10 mL of ethanol. This mixture was treated with 0.15 g of 10percent palladium on charcoal and placed under an atmosphere of 51 psig of hydrogen gas in a Parr shaker apparatus. A total of 14 psig of hydrogen was taken up in 16 hours. The reaction mixture was removed from the Parr shaker apparatus after dissipating the hydrogen gas, filtered through a Celite pad to remove the catalyst and concentrated to a white solid, 3-(4-n-Propylphenyl)propanoic acid (3.07 g). IH NMR <n="33"/>(d6-DMSO): delta 12.1, bs, IH (COOH); delta 7.09, d, 2H, (arylH's); delta 7.05, d, 2H (arylH's); delta 2.75, t, 2H, (CH2 beta to COOH); delta 2.47, m, 4H (CH2 alpha to COOH and CH2 alpha to aryl); delta 1.52, hex, 2H (CH2 beta to aryl); delta 0.85, t, 3H (CH3). 13C NMR (d6-DMS0): 173.76, 139.64, 138.01, 128.20, 128.02, 36.86, 35.28, 29.93, 24.11, 13.63.
  • 12
  • [ 4885-02-3 ]
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  • 13
  • [ 21398-43-6 ]
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  • [ 74800-65-0 ]
  • [ 81220-91-9 ]
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  • [ 52710-27-7 ]
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  • [ 104480-27-5 ]
  • [ 115883-95-9 ]
  • 17
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  • [ 927998-85-4 ]
  • [ 105745-98-0 ]
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  • [ 927998-87-6 ]
  • [ 105746-06-3 ]
  • 21
  • [ 28785-06-0 ]
  • [ 621-95-4 ]
  • N,N'-bis(p-n-propylbenzylidene)-α,α'-bi-p-toluidine [ No CAS ]
  • 24
  • [ 109-97-7 ]
  • [ 28785-06-0 ]
  • [ 100-52-7 ]
  • [ 917-23-7 ]
  • (p-Propylphenyl)triphenylporphyrin [ No CAS ]
  • 25
  • [ 28785-06-0 ]
  • LY264826 triacetate [ No CAS ]
  • C83H98Cl2N10O26 [ No CAS ]
  • 26
  • [ 28785-06-0 ]
  • [ 7393-43-3 ]
  • 1-(4-propyl-phenyl)-but-3-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 120℃; for 18h;Inert atmosphere; General procedure: According to the method of Molander, et. al. (J. Org. Chem. 2009, 74, 3636), a suspension of 5-bromo-2-formylfuran (695 mg, 3.97 mmol), hexylboronic acid (775 mg, 5.96 mmol), potassium carbonate ( 1.65 g, 11.91 mmol), palladium(II) acetate (18 mg, 0.079 mmol) and RuPhos (74 mg, 0.16 mmol) in 9: 1 toluene/water (22 mL) in a pressure-relief vial under argon was heated in a 120 °C bath for 18 h. After cooling to room temperature, the tion mixture was diluted with water (25 mL) and organics extracted with ether (3 x 50 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (10percent ethyl acetate in hexanes) to give 5-hexyl-2-formylfuran (665 mg, 93percent) as a clear oil. Used without further characterization.
According to the procedure of example 1a, upon substituting in place of the benzaldehyde, one of the following substituted benzaldehydes:...m-chlorobenzaldehydep-trifluoromethylbenzaldehydem-fluorobenzaldehydeo-methylbenzaldehydep-propylbenzaldehydem-ethoxybenzaldehydep-propoxybenzaldehyde
With bis(trichloromethyl) carbonate; 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine; triethylamine; In dichloromethane; at -30℃; for 1h;Inert atmosphere; General procedure: (1) To a 50 mL two-necked flask, 1.24 g (1.5 eq, 4.17 mmol) of 4- (2- (2- (methylsulfoxy) ethyl) -4-nitrophenyl) morpholine was added, Methyl chloride, magnetic stirring nitrogen protection, ice salt bath cooling to -30 ,A solution of 0.41 g (0.5 eq, 1.39 mmol) of bis (trichloromethyl) carbonate in 3 mL of anhydrous methylene chloride was added dropwise, stirring was continued for 0.5 h, and 0.3 g (2.78 mmol) of benzyl alcohol in 3 mL of anhydrous dichloromethane (3.0 eq, 8.34 mmol) of triethylamine was added dropwise. The reaction was complete by TLC. The mixture was stirred for 0.5 hours. The organic layer was separated and the dichloromethane was recovered under reduced pressure. The residue was added hydrochloric acid solution adjusted to pH 3, petroleum ether extraction separation, the organic layer vacuum recovery of petroleum ether 0.28g benzaldehyde, yield 94.9percent.(2) the aqueous layer of ice water bath drop sodium hydroxide solution adjusted to pH 10, dichloromethane extraction separation, organic layer vacuum recovery of methylene chloride was 0.95g by-product sulfide (VI) and excessive new sub- Sulfone (I). The structure of the by-product thioether (VI) was confirmed
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  • [ 2033-24-1 ]
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  • [ 162752-13-8 ]
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  • [ 5470-49-5 ]
  • [ 1027552-47-1 ]
  • 30
  • [ 418762-88-6 ]
  • [ 28785-06-0 ]
  • (2-Chloro-6-pyrrol-1-yl-benzyl)-[1-(4-propyl-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]
  • 31
  • [ 873787-91-8 ]
  • [ 28785-06-0 ]
  • [ 1026538-18-0 ]
  • 32
  • [ 28785-06-0 ]
  • [ 56041-85-1 ]
  • 3-(4-methylsulfanylphenyl)-1-(4-propylphenyl)prop-2-yn-1-ol [ No CAS ]
  • 33
  • 2-(4-propyl-phenyl)-[1,3]dioxolane [ No CAS ]
  • [ 28785-06-0 ]
  • 34
  • [ 868159-55-1 ]
  • [ 28785-06-0 ]
  • bis-1,3,2,4-(4'-propylbenzylidene)-1-propyl sorbitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In ethanol; for 24h; EXAMPLE 5 Bis-1,3,2,4-(4'-propylbenzylidene)-1-Propyl Sorbitol A one liter reaction kettle, equipped with a stirrer and nitrogen inlet, was charged with the propyl sorbitol ethanol solution. 40 g (0.27 mol) of <strong>[28785-06-0]4-propylbenzaldehyde</strong>, and 2.6 g of p-toulenesulfonic acid monohydrate was added to the reaction vessel. The clear solution was stirred for 24 hours, during which time a significant amount of white precipitate formed. The white powder was isolated by filtration and washed with 250 ml of 1 M NaOH aqueous solution. The white powder was suspended in water and further neutralized to pH=7 with a small amount of NaOH. The suspension was heated to boiling, then filtered. The white powder was washed with 7*500 ml of boiling water. The washed powder dried overnight. The white powder was then stirred in 500 mL of cyclohexane, heated until boiling, filtered, and washed with 2*250 ml of boiling cyclohexane. Further purification was accomplished by using an Ace Glass 6810 Giant Soxhlet Extraction Apparatus (size F) and cellulose fiber thimble (58*170 MM OD) with 2000 ml of methanol. The white powder was slurried in 250 ml of methanol, poured into the thimble, and extracted over 5 days of reflux. The resultant extract was chilled to 5° C. and filtered to collect the white solid, which was slurried in 1000 ml of petroleum ether, filtered, and air dried. The isolated white powder was dried in a vacuum oven to give 20.1 g of product, m.p. 244-245° C. The purity was above 99percent, based on GC-MS. 1H NMR(500 MHz, DMSO-d6, ppm): 0.86-0.89 (m, 6H, Ph-CH2CH2CH3), 0.91-0.94 (t, 3H, sugar-CH2CH2CH3), 1.35-1.49 (m, 2H, sugar-CH2CH2CH3) 1.54-1.60 (m, 4H, Ph-CH2CH2CH3), 1.61-1.71 (m, 2H, sugar-CH2CH2CH3), 2.53-2.56 (t, 4H, Ph-CH2CH2CH3), 3.41-4.04 (m, 7H, sugar H), 4.36-4.39 (t, 1H, -CH2OH), 4.78-4.79 (d, 1H, -CHOH), 5.60 (s, 1H, acetal), 5.62 (s, 1H, acetal), 7.17-7.20 (dd, 4H), 7.32-7.37 (dd, 4H).
  • 35
  • [ 28785-06-0 ]
  • [ 1576-35-8 ]
  • 4-propylbenzaldehyde tosylhydrazone [ No CAS ]
 

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