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Structure of 13468-02-5

Chemical Structure| 13468-02-5

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Product Details of [ 13468-02-5 ]

CAS No. :13468-02-5
Formula : C10H15NO
M.W : 165.23
SMILES Code : CN(C)CCOC1=CC=CC=C1
MDL No. :MFCD00040016
InChI Key :RUHVDRGWCIAFLG-UHFFFAOYSA-N
Pubchem ID :26050

Safety of [ 13468-02-5 ]

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

Computational Chemistry of [ 13468-02-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 50.25
TPSA ?

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

12.47 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.53
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

1.72
Log Po/w (WLOGP)?

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

1.63
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.

1.83
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

1.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.86

Water Solubility

Log S (ESOL):?

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

-2.05
Solubility 1.46 mg/ml ; 0.00883 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.

-1.6
Solubility 4.17 mg/ml ; 0.0252 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

-3.05
Solubility 0.148 mg/ml ; 0.000893 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.

-6.09 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<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)

1.26

Application In Synthesis of [ 13468-02-5 ]

* 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 [ 13468-02-5 ]

[ 13468-02-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 111-83-1 ]
  • [ 13468-02-5 ]
  • [ 10588-71-3 ]
  • 2
  • [ 13468-02-5 ]
  • [ 143-15-7 ]
  • [ 538-71-6 ]
  • 4
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  • [ 112-52-7 ]
  • [ 10561-60-1 ]
  • 5
  • [ 13468-02-5 ]
  • [ 112-82-3 ]
  • [ 10561-61-2 ]
  • 6
  • [ 13468-02-5 ]
  • [ 620-20-2 ]
  • (3-Chloro-benzyl)-dimethyl-(2-phenoxy-ethyl)-ammonium; iodide [ No CAS ]
  • 7
  • [ 13468-02-5 ]
  • [ 619-23-8 ]
  • Dimethyl-(3-nitro-benzyl)-(2-phenoxy-ethyl)-ammonium; iodide [ No CAS ]
  • 12
  • [ 13468-02-5 ]
  • [ 100-52-7 ]
  • [ 98684-34-5 ]
  • 13
  • [ 13468-02-5 ]
  • [ 75-03-6 ]
  • [ 137325-68-9 ]
  • 14
  • [ 13468-02-5 ]
  • [ 68-12-2 ]
  • [ 15182-06-6 ]
  • 15
  • [ 13468-02-5 ]
  • [ 74-88-4 ]
  • [ 21982-87-6 ]
  • 16
  • [ 2862-39-7 ]
  • [ 108-95-2 ]
  • [ 13468-02-5 ]
  • 17
  • [ 13468-02-5 ]
  • [ 4101-68-2 ]
  • [ 14704-78-0 ]
  • 18
  • [ 13468-02-5 ]
  • 2-(dimethylaminoethoxy)phenyllithium [ No CAS ]
  • 19
  • [ 64-17-5 ]
  • [ 141-52-6 ]
  • [ 108-95-2 ]
  • hydrochloride of dimethyl-<β-chloro-ethyl>-amine [ No CAS ]
  • [ 13468-02-5 ]
  • 22
  • [ 108-95-2 ]
  • 1.4-dimethyl-piperazine-bis-< metho-<i>p</i>-toluenesulfonate> [ No CAS ]
  • [ 13468-02-5 ]
  • 23
  • [ 108-95-2 ]
  • hydrochloride of dimethyl-<β-chloro-ethyl>-amine [ No CAS ]
  • [ 13468-02-5 ]
  • 24
  • [ 64-17-5 ]
  • [ 122596-11-6 ]
  • [ 108-95-2 ]
  • KOH [ No CAS ]
  • [ 13468-02-5 ]
  • 25
  • [ 13468-02-5 ]
  • 3C10H14NNaO*2C6H6 [ No CAS ]
  • 26
  • [ 13468-02-5 ]
  • C10H14NNaO [ No CAS ]
  • 27
  • [ 701-99-5 ]
  • [ 13468-02-5 ]
  • 28
  • [ 122-59-8 ]
  • [ 13468-02-5 ]
  • 30
  • [ 13468-02-5 ]
  • [ 259183-86-3 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid; In dichloromethane; Intermediate Example 2 Preparation of [2-(dimethylamino)ethoxy]phenyl-4-sulfonyl chloride 2 g of <strong>[13468-02-5]N,N-dimethyl-N-[(2-phenoxy)ethyl]amine</strong> was dissolved in 10 ml of dichloromethane and 3 ml of chlorosulfonic acid was slowly added under ice cooling. The mixture was stirred at room temperature for 3 hr and poured into ice. Dichloromethane (100 ml) was added and aqueous layer was neutralized by concentrated sodium carbonate solution with keeping temperature under 4 C. Dichloromethane layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. 0.8 g of [2-(dimethylamino)ethoxy]phenyl-4-sulfonyl chloride was obtained.
With chlorosulfonic acid; In dichloromethane; at 20℃; for 3.0h;Cooling with ice; The N, N - dimethyl - N - [(2 - phenoxy) ethyl] amine (1.65 g, 10 . 00 mmol) dissolved in dichloromethane (10 ml) in, under ice bath slowly [...] sulfonic acid (2.5 ml The system for the ice in the pouring, adding dichloromethane (50 ml), separating the organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude intermediate 6 a, directly Used for the next step reaction.
  • 31
  • [ 13468-02-5 ]
  • [ 866414-63-3 ]
YieldReaction ConditionsOperation in experiment
74% Example 5 - Sodium 4-(2-dimethylaminoethoxy)-benzenesulfonate 7.00 g (42.4 mmol) of dimethyl-(2-phenoxyethyl)-amine were dissolved in 35 mL of glacial acetic acid and cooled in an ice bath. 9.63 g (93.3 mmol) of 95% sulfuric acid were dropped in while maintaining an internal temperature of 10C or lower followed by stirring for 1 hour at room temperature. The solution was concentrated followed by the gradual addition of the concentrated residue to 1 mol/L sodium hydroxide to bring pH10, after which the solution was concentrated and dried. After extracting the residue with methanol, concentrating and drying, the residue was suspended in 100 mL of ethanol followed by cooling and filtration. The filtrate was concentrated and the precipitated crystals were filtered to obtain 8.36 g of the target substance (yield: 74%). 1H-NMR (400 MHz, D2O): delta = 7.68 (d,2H,J=8.8 Hz), 7.01 (d,2H,J=8.8 Hz), 4.33 (t,2H,J=5.0 Hz), 3.53 (t,2H,J=5.2 Hz) 13C-NMR (400 MHz, D2O): delta = 158.12, 133.61, 125.61, 112.90, 61.79, 59.66, 41.70 IR (KBr): nu = 3431, 3097, 2770, 1599, 1180, 1032, 844 cm-1
  • 32
  • [ 122-99-6 ]
  • [ 124-40-3 ]
  • [ 13468-02-5 ]
  • 33
  • [ 1391906-41-4 ]
  • [ 108-95-2 ]
  • [ 13468-02-5 ]
  • 34
  • [ 20570-41-6 ]
  • [ 108-95-2 ]
  • [ 13468-02-5 ]
  • 35
  • [ 4584-46-7 ]
  • [ 108-95-2 ]
  • [ 13468-02-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide; In ethanol; water; at 55 - 60℃; for 4.0h; The phenol 94g (1mol), potassium hydroxide 117.6g (2.1mol) was added 600ml ethanol and stirred to dissolve, temperature at 55 ~ 60 reaction slowly added dropwiseN, N- dimethyl-chloroethane hydrochloride 158g (1.1mol, was dissolved in 300g water), the addition was complete reaction was continued for 4 hours; the reaction was completed, recovering ethanol, then extracted twice with dichloromethane, combined, washed with water and concentrated to give an oil 142g XI, a yield of 86.0%;
 

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