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Chemical Structure| 15666-97-4 Chemical Structure| 15666-97-4

Structure of 15666-97-4

Chemical Structure| 15666-97-4

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Product Details of [ 15666-97-4 ]

CAS No. :15666-97-4
Formula : C11H19NO2
M.W : 197.27
SMILES Code : O=C(OCCCCCCCC)CC#N
MDL No. :MFCD00075425
InChI Key :MBCTWXWDQMXVDF-UHFFFAOYSA-N
Pubchem ID :4384482

Safety of [ 15666-97-4 ]

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

Computational Chemistry of [ 15666-97-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 9
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 56.02
TPSA ?

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

50.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.72
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

3.3
Log Po/w (WLOGP)?

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

2.8
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.

1.88
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

2.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.7

Water Solubility

Log S (ESOL):?

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

-2.55
Solubility 0.558 mg/ml ; 0.00283 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.

-4.03
Solubility 0.0185 mg/ml ; 0.0000939 mol/l
Class?

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

Moderately 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

-3.29
Solubility 0.102 mg/ml ; 0.000519 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.

-5.16 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)

2.3

Application In Synthesis of [ 15666-97-4 ]

* 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 [ 15666-97-4 ]

[ 15666-97-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 15666-97-4 ]
  • [ 100-52-7 ]
  • 3<i>t</i>-phenyl-2-cyano-acrylic acid octyl ester [ No CAS ]
  • 3
  • [ 10467-10-4 ]
  • [ 15666-97-4 ]
  • [ 92445-21-1 ]
  • 4
  • [ 75-15-0 ]
  • [ 15666-97-4 ]
  • C12H17NO2S2(2-)*2K(1+) [ No CAS ]
  • 5
  • [ 111-87-5 ]
  • [ 372-09-8 ]
  • [ 15666-97-4 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; at 80 - 125℃; In step 1 of Figure 1, in a 1 liter round bottom flask, 136 g of 1-octanol was mixed with 350 g of toluene, the flask was placed in a heating mantle and maintained on a magnetic stirrer,The mixture was stirred vigorously at 80 DEG C to form a mixed solution.As step 120 of Figure 1,86 g of 2-cyanoacetic acid and 0.5 g of p-toluenesulfonic acid were gradually added to the flask, and a water condenser was connected to the flask through a trap and a calcium chloride guide tube.The temperature was 125 CAnd the esterification reaction was carried out.As step 130 of Figure 1, the water formed during the esterification reaction was azeotrope-formed and removed while azeotropic distillation was continued until the total amount of water collected was 17 mL. The distillation was then stopped and the flask was cooled to room temperature. The contents of the flask were filtered with a Buchner funnel, and the filtrate was extracted three times with a 10% sodium hydrogencarbonate solution and water using a 1 liter separatory funnel, respectively. The obtained organic layer was dried over anhydrous magnesium sulfate for 12 hours.Then toluene was added to 85In And then removed by rotary evaporation.Results 1-Octyl-2-cyanoacetate was analyzed by FT-IR spectrophotometer and the results are shown in FIG.
  • 6
  • [ 15666-97-4 ]
  • [ 122-51-0 ]
  • [ 64845-29-0 ]
  • 7
  • [ 15666-97-4 ]
  • [ 670-54-2 ]
  • n-Octyl tricyanoacrylate [ No CAS ]
  • [ 109-77-3 ]
  • 8
  • [ 116-31-4 ]
  • [ 15666-97-4 ]
  • Retinyliden-malonsaeure-octylester-mononitril [ No CAS ]
  • 9
  • [ 556-18-3 ]
  • [ 15666-97-4 ]
  • (E)-3-(4-Amino-phenyl)-2-cyano-acrylic acid octyl ester [ No CAS ]
  • 10
  • [ 766-40-5 ]
  • [ 15666-97-4 ]
  • octyl cyano-(3,4-dichloro-5-oxo-2,5-dihydro-furan-2-yl)-acetate [ No CAS ]
  • 11
  • [ 766-38-1 ]
  • [ 15666-97-4 ]
  • octyl cyano-(3,4-dibromo-5-oxo-2,5-dihydro-furan-2-yl)-acetate [ No CAS ]
  • 12
  • [ 15666-97-4 ]
  • [ 106-93-4 ]
  • [ 855596-19-9 ]
  • 13
  • [ 15666-97-4 ]
  • (E)-2-Cyano-3-[4-(4-piperidin-1-yl-phenylazo)-phenyl]-acrylic acid octyl ester [ No CAS ]
  • 14
  • [ 15666-97-4 ]
  • (Z)-2-Cyano-3-methylamino-acrylic acid octyl ester [ No CAS ]
  • 15
  • [ 15666-97-4 ]
  • (Z)-3-Butylamino-2-cyano-acrylic acid octyl ester [ No CAS ]
  • 16
  • [ 15666-97-4 ]
  • [ 92445-22-2 ]
  • 17
  • [ 15666-97-4 ]
  • [ 92445-22-2 ]
  • 18
  • [ 92445-22-2 ]
  • [ 15666-97-4 ]
  • 19
  • [ 97189-65-6 ]
  • [ 15666-97-4 ]
  • 20
  • [ 15666-97-4 ]
  • [ 2351-37-3 ]
  • 2-cyano-3-[4'-(2-cyano-1-hydroxy-2-octyloxycarbonyl-vinyl)-biphenyl-4-yl-3-hydroxy] acrylic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With lithium diisopropyl amide; In tetrahydrofuran; at -78℃; for 0.75h; Preparation of aryl-bis-(2-cyano-3-hydroxy-acrylic acid) ester (102): R = N-OCTYL, I-OCTYL (102) A 1.6 m solution MMOL of n-BuLi in hexane is added at-10C to a solution of 1 mmol diiso- propylamine in THFabs (6 ML/ML DIISOPROPYLAMINE). The mixture is stirred for 15 min. and than cooled down to-78C. After that the solution of 0.5 mmol of the corresponding cyano acetate is added in THF (1 MI/ g cyanoacetate) at this temperature initially, additionally stirred for 15 min and than the SOLU- tion of 0.5 mmol of the acid chloride is added in THF (2 ML/G acid chloride). After stirring of 45 min AT-78C the reaction mixture is quenched at this temperature with 15 % HCI und warmed up to room temperature over night.
  • 21
  • [ 4805-22-5 ]
  • [ 15666-97-4 ]
  • [ 1239599-06-4 ]
  • 22
  • [ 98057-08-0 ]
  • [ 15666-97-4 ]
  • (Z,Z)-5,5'-bis(α-cyano-α-octanoxycarbonylmetylene)-5,5'-dihydro-Δ2,2':5',2''-terthiophene [ No CAS ]
  • 23
  • [ 1353649-36-1 ]
  • [ 15666-97-4 ]
  • [ 1353649-37-2 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; In chloroform; at 20℃; for 40h;Inert atmosphere; Under argon gas protection, to a two-ported flask filled with 3T(BDT)3T(CHO)2 (1.0 g, 0.71 mmol), <strong>[15666-97-4]octyl cyanoacetate</strong> (10-folds molar equivalent) and 70 mL of dry trichloromethane was added dropwise several drops of triethylamine. The mixture was stood at room temperature for 40 h and then was poured into 100 mL of water and extracted with dichloromethane (50 mL×3). The organic phase was washed with water (100 mL), saturated saline (100 mL) and water (100 mL), successively. The organic phase was dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the resultant product was separated with chromatographic column, in which petroleum ether-dichloromethane (2:3) was eluant, to give a black solid (yield: 70%). MALDI-TOF MS (m/z): C106H148N2O4S8 [M]+, calculated: 1768.92; found: 1768.93.
  • 24
  • [ 71091-89-9 ]
  • dicyclohexylammonium α-cyanoacrylate [ No CAS ]
  • n-octyl 2-cyanoacrylate [ No CAS ]
  • [ 629-82-3 ]
  • [ 1215021-90-1 ]
  • [ 15666-97-4 ]
  • [ 15802-18-3 ]
YieldReaction ConditionsOperation in experiment
65% With trifluoroacetic acid; In dichloromethane; at 22℃;Product distribution / selectivity; To a solution of octyl triflate (0.05 mol) in dry dichloromethane (DCM, 100 mL) was added trifluoroacetic acid [TFA] (0.004 mol) and t-butylated hydroxyanisole (0.25 wt%). A solution of Dicyclohexylammonium alpha-cyanoacrylate in dry DCM (80mL) was added dropwise (2h). The resulting solution was stirred at 22 C overnight. NMR showed approx 10% of the triflate remaining with no trace of polymer. A solution of 0.078 mol of Dicyclohexylammonium alpha-cyanoacrylate in dry DCM (20 mL) was added. The mixture was stirred at 22 C until triflate had disappeared in the NMR (4h). The mixture was acidified (TFA) and reduced in vacuo. The precipitated solid was removed by filtration. Hexane (100 mL) was added. The mixture was reduced and filtered again. This was repeated. The solvents were removed to afford 1 1.5g of a yellow liquid which was -75- 80% CA monomer. The impurities are cyanoacrylic acid (due to the excess ofDicyclohexylammonium alpha-cyanoacrylate used), dioctyl ether (a byproduct carried through from the triflate formation) a small amount (<2%) of polymer, trace amounts of the amine triflate salt, octyl cyanoacetate (formed from cyanoacetic acid amine salt, a residue from incomplete formation of the Dicyclohexylammonium alpha-cyanoacrylate). There are no byproducts or side reaction evident from the CA formation reaction. The octyl CA was distilled to purify and afforded an overall yield of 65% based on triflate. The synthesis procedure is general and has been used to prepare crude samples of other monomers such as n-propyl CA, 3-methoxybutyl CA and bis-cyanoacrylic acid ester of PEG 400.[0060] NMR Analysis of distilled material: 1H NMR (CDCI3) delta : 7.05, (s, 1 H, =CHH); 6.65 (s, 1 H, =CHH); 4.27 (t, 2H, ~COOCH2CH2~); 1.73 (m, 2H, ~COOCH2CH2~); 1 .40-1.25 (br m, 10H, ~COOCH2CH2CH2CH2 CH2CH2CH2~); 0.88 (t, 3H, ~CH2CH3).[0061] 13C 5 : 163.27 ~COO~; 143.3, =CH2; 1 14.5, ~CN; 1 13.4, ~C=CH2; 66.99, ~COOCH2~; 31 .8; 29.2; 28.4; 25.8; 24.7; 22.7 (~CH2CH3); 14.1 1 (~CH3).
  • 25
  • [ 1397243-02-5 ]
  • [ 15666-97-4 ]
  • [ 1397242-69-1 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In chloroform; at 20℃;Inert atmosphere; Under argon gas protection, to a two-neck flask filled with bis(formyltrithiophene)silole (147 mg, 0.104 mmol), <strong>[15666-97-4]octyl cyanoacetate</strong> (10-folds molar equivalent) and 50 mL of dry trichloromethane was added dropwise several drops of triethylamine. The mixture was stirred at room temperature overnight. The mixture was poured into 100 mL of water and extracted with dichloromethane (20 mL×3). The organic phase was washed with water (50 mL), saturated saline (50 mL) and water (50 mL), successively. The organic phase was dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the resultant product was separated with chromatographic column, in which petroleum ether-dichloromethane (1:1) was eluant, to give a brown solid (yield: 90%). MALDI-TOF MS (m/z): C90H124N4O6S7 [M]+, calculated: 1773.9; found: 1773.9.
  • 26
  • [ 1397243-03-6 ]
  • [ 15666-97-4 ]
  • C106H150N2O5S8 [ No CAS ]
  • 27
  • 5',5''',5'''''-((1E,1'E,1"E)-(nitrilotris(benzene-4,1-diyl))tris(ethene-2,1-diyl))tris(([2,2'-bithiophene]-5-carbaldehyde)) [ No CAS ]
  • [ 15666-97-4 ]
  • C84H84N4O6S6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Ca. 40% With triethylamine; In chloroform; at 75℃; for 24h;Reflux; To a solution of residue Compound 5 (0.9 g, 1.00 mmol) in 50 mL of chloroform, <strong>[15666-97-4]octyl cyanoacetate</strong> (1.97 g, 10.0 mmol) and 1.5 ml triethylamine were added and the mixture was refluxed at 75 C for 24 h under nitrogen. After returning to room temperature dichloromethane was added, the solution was washed with water and dried over Na2SO4. After solvent removal, the residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate 1:1) to give 575 mg of black solid with a yield of ca. 40%. MALDI-TOF MS: 1436.3, calculated for C84H84N4O6S6 1436.47. 1H NMR (400 MHz, CDCl3): delta(ppm) 8.25 (s, 3H), 7.67-7.66 (d, J = 4.0 Hz, 3H), 7.41-7.38 (d, J = 8.0 Hz, 6H), 7.32-7.30 (d, J = 8.0 Hz, 3H), 7.25-7.23 (d, J = 6.0 Hz, 3H), 7.12-7.08 (d, J = 8.6 Hz, 9H), 7.04-7.00 (d, J = 10.0 Hz, 3H), 6.96-6.91 (d, J = 12.0 Hz, 3H), 4.31-4.27 (t, 6H), 1.79-1.71 (m, 6H), 1.42-1.40 (m, 6H), 1.32-1.29 (d, J = 10.0 Hz, 24H), 0.91-0.87 (t, 9H). 13C NMR (400 MHz, CDCl3): delta(ppm) 163.14, 147.55, 146.09, 145.55, 139.24, 134.24, 133.94, 127.70, 127.26, 124.43, 124.24, 116.14, 97.62, 66.65, 31.83, 29.24, 29.21, 22.70, 14.17.
  • 28
  • C104H138O4S10 [ No CAS ]
  • [ 15666-97-4 ]
  • C126H172N2O6S10 [ No CAS ]
  • 29
  • [ 1445733-68-5 ]
  • [ 15666-97-4 ]
  • [ 1445733-72-1 ]
  • 30
  • [ 1445733-67-4 ]
  • [ 15666-97-4 ]
  • [ 1445733-70-9 ]
  • 31
  • C37H55BrOS3 [ No CAS ]
  • [ 15666-97-4 ]
  • C48H72BrNO2S3 [ No CAS ]
  • 32
  • C25H37BrOS2 [ No CAS ]
  • [ 15666-97-4 ]
  • C36H54BrNO2S2 [ No CAS ]
  • 33
  • C65H80O4S6 [ No CAS ]
  • [ 15666-97-4 ]
  • C87H114N2O6S6 [ No CAS ]
  • 34
  • C65H80O2S8 [ No CAS ]
  • [ 15666-97-4 ]
  • C87H114N2O4S8 [ No CAS ]
  • 35
  • C65H80O2S6Se2 [ No CAS ]
  • [ 15666-97-4 ]
  • C87H114N2O4S6Se2 [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 15666-97-4 ]

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