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Chemical Structure| 2016-57-1 Chemical Structure| 2016-57-1

Structure of 2016-57-1

Chemical Structure| 2016-57-1

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Product Details of [ 2016-57-1 ]

CAS No. :2016-57-1
Formula : C10H23N
M.W : 157.30
SMILES Code : CCCCCCCCCCN
MDL No. :MFCD00008149
InChI Key :MHZGKXUYDGKKIU-UHFFFAOYSA-N
Pubchem ID :8916

Safety of [ 2016-57-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311-H314-H400
Precautionary Statements:P273-P280-P301+P310-P305+P351+P338-P310
Class:8(6.1)
UN#:2922
Packing Group:

Computational Chemistry of [ 2016-57-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 8
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 52.89
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.97
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

-0.03
Log Po/w (WLOGP)?

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

3.09
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.

2.84
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

2.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.33

Water Solubility

Log S (ESOL):?

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

-0.27
Solubility 84.8 mg/ml ; 0.539 mol/l
Class?

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

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.07
Solubility 135.0 mg/ml ; 0.858 mol/l
Class?

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

Very 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

-3.54
Solubility 0.0456 mg/ml ; 0.00029 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.

-7.28 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

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)

1.43

Application In Synthesis of [ 2016-57-1 ]

* 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 [ 2016-57-1 ]

[ 2016-57-1 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 2016-57-1 ]
  • [ 57-92-1 ]
  • [ 56222-69-6 ]
  • 3
  • [ 2016-57-1 ]
  • [ 34374-88-4 ]
  • 2,4-Bis-[(E)-decyliminomethyl]-6-[(Z)-decyliminomethyl]-benzene-1,3,5-triol [ No CAS ]
  • 4
  • [ 2016-57-1 ]
  • [ 546-43-0 ]
  • [ 1245719-09-8 ]
  • 5
  • [ 2016-57-1 ]
  • [ 63547-24-0 ]
  • [ 1410075-15-8 ]
  • 6
  • [ 2016-57-1 ]
  • [ 19064-24-5 ]
  • [ 1423875-66-4 ]
YieldReaction ConditionsOperation in experiment
81.1% With potassium carbonate; In N,N-dimethyl acetamide; toluene; at 125℃; for 17h;Dean-Stark; General procedure: The preparation of compound A7 is provided as a representative synthesis procedure of these compounds. (0012) Heptylamine (1.3186 g, 0.0114 mol) and 2,4-DFNB, (0.9262 g, 0.0058 mol) were weighed into separate vials. Potassium carbonate (3.03 g, 0.022 mol, 50% excess) was transferred to a 100 mL three-necked round-bottomed flask fitted with a magnetic stir bar, nitrogen inlet, thermometer, and a Dean-Stark trap fitted with a condenser. Each glass vial used for weighing starting materials was rinsed with DMAC (5 mL) and the washings were transferred to the reaction vessel to ensure full transfer of any residual reagents. Next, an additional 4 mL of DMAC was added to the reaction vessel, followed by 15 mL of toluene. An initial exotherm of 5 C was observed upon the dissolution of the starting materials, rendering the reaction mixture bright yellow in color. The reaction vessel was heated by an external temperature-controlled oil bath (with mild stirring) for 17 h at 125 C. At the completion of the reaction, the vessel was cooled, the reaction mixture was diluted with dichloromethane, and then filtered through celite to remove all salts. The filtrate was evaporated at reduced pressure to yield a crude product that was subsequently dissolved in dichloromethane and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated at reduced pressure, and the resulting solid was further purified via recrystallization in absolute ethanol to yield yellow needles. Spectroscopic data for the secondary amines are supplied as Supplementary data.
  • 7
  • [ 2016-57-1 ]
  • [ 3543-75-7 ]
  • [ 1609623-14-4 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 2.7 - 10℃; for 1.5h;Inert atmosphere; 4-{5-[Bis-(2-chloro-ethyl)-amino]-l-methyl-lH-benzoimidazol-2-yl}-N-decyl-butyramide (<strong>[3543-75-7]bendamustine</strong> do amide): A 250 mL three neck round bottom flask equipped with a stir bar, thermocouple, cooling bath, 60 mL pressure equalizing dropping funnel and nitrogen in/outlet was charged with 10.0 g (25.3 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 10.6 g (27.8 mmol) of HATU and 100 mL of Nu,Nu-dimethylfomramide (DMF). To this stirred yellow solution was added 4.41 mL (3.27 g, 25.3 mmol) of Nu,Nu-diisopropylethyelamine (DIPEA). An exotherm to 27.1C was noted and the solution became a darker yellow. The reaction was cooled to 6.6C where a solution of 6.2 mL (4.59 g, 35.5 mmol) of DIPEA, 5.11 mL (4.1 g, 25.6 mmol) of decyl amine in 20 mL of DMF was added drop-wise over 13 min at 2.7-7.6C. Once addition was complete the reaction was allowed to stir at <10C for 1.5 hours at which time an in process analysis indicated the reaction was complete. The batch was quenched onto 200 mL of DI water and extracted with ethyl acetate (2 X 175 mL). The organic phases were combined, washed with 10% sodium hydrogen phosphate (I X 200 mL), 8% aqueous sodium bicarbonate (I X 200 mL) and brine (I X 200 mL) before concentrating to dryness in vacuo to give a sticky white solid. This solid was triturated with heptanes (75 mL) and became a flowable solid which was isolated by vacuum filtration. The wetcake was dried in a vacuum oven at 25C overnight to yield 13.33 g (25.3 mmol, 100%) of the desired product as a white solid with an HPLC purity of 98.0 lA^o.1 NMR (400 MHz, DMSO-d6) delta 7.72 (s, b, 1H), 7.33 (d, J= 8.76 Hz, 1H), 6.91 (d, J = 2.28 Hz, 1H), 6.80 (dd, J= 2.36, 8.8 Hz), 3.7 (s, 8H), 3.66 (s, 3H), 3.01 (q, J= 6.8, 12.68, 2H), 2.79 (t, J= 7.44 Hz, 2H), 2.18 (t, J= 7.36 Hz, 2H), 1.95 (m, 2H), 1.36 (m, 2H), 1.22 (s, b, 14), 0.84 (t, J= 6.68 Hz, 3H).
  • 8
  • [ 2016-57-1 ]
  • [ 16499-62-0 ]
  • N-decyl-7-fluoroquinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In isopropyl alcohol; for 6h;Reflux; A mixture of 1-decylamine (1.2 mL, 6.0 mmol), <strong>[16499-62-0]4-chloro-7-fluoroquinazoline</strong> (1.1 g, 6.0 mmol), and TEA (1.3 mL, 9.3 mmol) in 10 mL of IPA was heated at reflux for 6 hr. Then, the volatile components were evaporated, and the residue was partitioned between DCM (400, 300 mL) and 5% Na2C03 (400 mL). The organic phases were dried over anhydrous Na2S04, filtered through a pad of silica gel, washing with 10% MeOH/DCM, and concentrated. The product was crystallized from EA/Hex.
  • 9
  • [ 2016-57-1 ]
  • [ 1426827-79-3 ]
  • N-[(1R,8S,9S)-bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1-aminodecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine; In dichloromethane; at 20℃; for 18h;Inert atmosphere; Darkness; To a solution of n-decylamine (10 μL, 0.05 mmol) in CH2Cl2 (5 mL) were added Et3N (16 μL, 0.11 mmol) and <strong>[1426827-79-3]BCN-NHS</strong> (15 mg, 0.05 mmol), and the mixture was stirred at room temperature under an inert atmosphere of N2 in the dark for 18 h. The reaction was then quenched with H2O (10 mL). The product was extracted with CH2Cl2 (10 mL*3) and the combined organic extract was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using n-hexane as the eluent. The solvent was removed under reduced pressure and the product was subsequently isolated as yellowish oil. Yield: 16 mg (87%). 1H NMR (400 MHz, CDCl3, 298 K, TMS): δ 4.67 (s, 1H), 4.16 (d, J=8.0 Hz, 2H), 3.18 (d, J=6.4 Hz, 2H), 2.34-2.21 (m, 6H), 1.68-1.59 (m, 2H), 1.52-1.45 (m, 1H), 1.44-1.37 (m, 16H), 0.99-0.94 (m, 2H), 0.89 (t, J=6.8 Hz, 3H). 13C NMR (100 MHz, CDCl3, 298 K, TMS): δ 156.7, 98.8, 62.6, 41.1, 31.9, 30.0, 29.5, 29.3, 29.1, 26.8, 22.7, 21.4, 20.1, 17.8, 14.1. Positive-ion ESI-MS ion cluster at m/z 334 [M+H]+.
 

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