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Chemical Structure| 17464-88-9 Chemical Structure| 17464-88-9

Structure of 17464-88-9

Chemical Structure| 17464-88-9

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Product Details of [ 17464-88-9 ]

CAS No. :17464-88-9
Formula : C12H22N4O6
M.W : 318.33
SMILES Code : COCN1C2C(N(COC)C1=O)N(COC)C(=O)N2COC
MDL No. :MFCD00402438
InChI Key :XGQJGMGAMHFMAO-UHFFFAOYSA-N
Pubchem ID :87125

Safety of [ 17464-88-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P280

Computational Chemistry of [ 17464-88-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 22
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 8
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 88.33
TPSA ?

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

84.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.84
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

-1.08
Log Po/w (WLOGP)?

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

-1.99
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.

-1.42
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

-2.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.03

Water Solubility

Log S (ESOL):?

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

-0.61
Solubility 79.0 mg/ml ; 0.248 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.

-0.19
Solubility 203.0 mg/ml ; 0.638 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

0.24
Solubility 560.0 mg/ml ; 1.76 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

No
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

Yes
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.

-9.01 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

0.0
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)

3.98

Application In Synthesis of [ 17464-88-9 ]

* 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 [ 17464-88-9 ]

[ 17464-88-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 17464-88-9 ]
  • [ 107-98-2 ]
  • 1,3,4,6-tetrakis(1'-methyl-2'-methoxy)ethoxymethylglycoluril [ No CAS ]
YieldReaction ConditionsOperation in experiment
99.8% With Amberlyst 15 resin; at 60℃; for 17.0h;Catalytic behavior; The Amberlyst 15 resin was dried in an oven to 60% of the original weight.3 g of <strong>[17464-88-9]tetramethoxymethylglycoluril</strong> was added to a 250 ml three-necked flask, 6 g of Amberlyst15 resin after drying, and 70 g of PGME were added, and the temperature was raised to 60 C. The reaction was stirred at -0.07 MPa for 17 hours while the produced methanol was distilled off.The reaction was filtered through a Buchner funnel and the filter was washed twice with PGME to recover the resin.The filtrate and the washing solution were combined and the solvent PGME was distilled off under reduced pressure to obtain 5.19 g of 1,3,4,6-tetrakis (1'-methyl-2'-methoxy) ethoxymethylglycol, 99.8%
With AMBERLYST; at 25 - 60℃; under 80 - 100 Torr; for 7.0h; 60 g (0.188 mol) of <strong>[17464-88-9]tetramethoxymethylglycoluril</strong> (product name: POWDERLINK [registered trademark] 1174 commercially available from Japan Cytec Industries, hereinafter abbreviated as PL-LI in this specification), 1,200 g of propylene glycol monomethyl ether (hereinafter abbreviated as PGME in this specification), and 120 g of a washed ion-exchange resin for a catalyst (product name: AMBERLYST [registered trademark] 15JWET, commercially available from Dow Chemical Company, hereinafter abbreviated as 15JWET in this specification) were put into a 2,000 mL flask, and the mixture was stirred and dissolved at 25° C. and then heated and stirred under a reduced pressure (80 Torr to 100 Torr) at 60° C. for 7 hours. Then, the pressure inside the flask was recovered and cooling was performed to 25° C., and then 15JWET was filtered off to obtain a desired compound (hereinafter abbreviated as PGME-PL in this specification). The obtained compound was identified by 1H NMR. As a result, it was confirmed that a peak (31.9 ppm) of a methoxy group of PL-LI disappeared and about 4 molecules of PGME were introduced into one molecule of PL-LI, and the glycoluril derivative of Formula (1A-1) (hereinafter abbreviated as PGME-PL in this specification) was obtained. [1.0 to 1.1 ppm (3H, ?CH3), 3.2 to 3.3 ppm (20H, ?OCH3 and ?CH2O?), 3.6 to 3.8 ppm (4H, ?OCH<)]
  • 2
  • [ 496-46-8 ]
  • [ 17464-88-9 ]
  • [ 80262-44-8 ]
  • [ 259886-51-6 ]
  • [ 259886-50-5 ]
YieldReaction ConditionsOperation in experiment
Ca. 58%Spectr.; Ca. 9%Spectr.; Ca. 28%Spectr. With methanesulfonic acid; at 80 - 100℃; for 18.0h; Synthesis of cucurbit[n]urils in methanesulphonic acid usingTetramethoxymethylglycoluril (TMMG)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 ml_) were placed in a reaction flask and heated to 80 °C. TMMG (44.66 g) was added in drop-wise and the reaction mixture was then heated to 100 °C (internal temp) for 18 hours. The reaction mixture was cooled and added to methanol (410 ml) to produce a beige powder which was analysed by1H NMR. Approximate Yields b1H NMR (percent of recovered product) cucurbit[5]uri 5percent, cucurbit[6]uri 58percent, cucurbit[7]uril 28percent, cucurbit[8]uril 9percent, cucurbit[9]uril 0percent, cucurbit[10]uril 0percent, cucurbit[11]uril 0percent
 

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