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Chemical Structure| 98955-27-2 Chemical Structure| 98955-27-2

Structure of 98955-27-2

Chemical Structure| 98955-27-2

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Product Details of [ 98955-27-2 ]

CAS No. :98955-27-2
Formula : C9H18O2
M.W : 158.24
SMILES Code : OCC1CCC(COC)CC1
MDL No. :MFCD22571682
InChI Key :KSIFEWSPJQDERU-UHFFFAOYSA-N
Pubchem ID :19938783

Safety of [ 98955-27-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H227-H315-H319-H335
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 98955-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 45.51
TPSA ?

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

29.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.37
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

1.11
Log Po/w (WLOGP)?

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

1.43
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.

1.22
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

1.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.56

Water Solubility

Log S (ESOL):?

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

-1.32
Solubility 7.53 mg/ml ; 0.0476 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.

-1.32
Solubility 7.54 mg/ml ; 0.0477 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

-1.44
Solubility 5.81 mg/ml ; 0.0367 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.

-6.48 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)

2.47

Application In Synthesis of [ 98955-27-2 ]

* 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 [ 98955-27-2 ]

[ 98955-27-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 105-08-8 ]
  • [ 74-88-4 ]
  • [ 98955-27-2 ]
  • 2
  • [ 120-61-6 ]
  • [ 94-60-0 ]
  • [ 105-08-8 ]
  • [ 98955-27-2 ]
  • bis(4-hydroxymethylcyclohexyl) ether [ No CAS ]
  • 3
  • CH3 I [ No CAS ]
  • [ 105-08-8 ]
  • ammonium chloride [ No CAS ]
  • [ 7757-82-6 ]
  • [ 98955-27-2 ]
YieldReaction ConditionsOperation in experiment
With NaH; In N,N-dimethyl-formamide; 1,4-bis(Hydroxymethyl)cyclohexane (5 g, 0.0347 mol), cis/trans mixture 1:3, in anhydrous DMF (20 cm3) was added dropwise to NaH (1.6 g, 0.0366 mol, 55%) washed with hexane, under atmosphere of nitrogen. The mixture was stirred at room temperature for 1/2 h, then CH3 I (5 g, 0.0352 mol) dissolved in DMF (20 cm3) was added dropwise. After the addition was complete the solution was stirred at room temperature for 2 h; NH4 Cl solution was added then thoroughly extracted with ether, to which Na2 SO4 was added and dried under reduced pressure. Chromatography on silica gel eluding with hexane/ethyl acetate (55/45) gave 4-methoxymethyl-cyclohexylmethanol (1.8 g, 0.0113 mol) out of 4.1 g of residue.
  • 4
  • [ 7757-82-6 ]
  • [ 98955-27-2 ]
  • [ 141604-50-4 ]
YieldReaction ConditionsOperation in experiment
With phosphorus tribromide; Such compound was dissolved in ether (10 cm3), cooled to -70 C. and was added dropwise with PBr3 (1.2 g, 0.0044 mol). After the addition was complete the solution was stirred to room temperature for 2 h, was extracted with ether and cautiously added with satured NaHCO3 solution. After the two layers were separated, the organic phase was added with Na2 SO4 and dried under reduced pressure. Chromatography on silica gel eluding with hexane gave 4-methoxymethyl cyclohexylmethyl bromide, cis trans mixture 1 3. Such product was employed in the example 8. 1 H-NMR (60 MHz, CCl4): delta0.6-2.2 (m), 10H; delta2.9-3.5 (m), 4H; delta3.25 (s), 3 H.
  • 5
  • [ 105-08-8 ]
  • [ 98955-27-2 ]
YieldReaction ConditionsOperation in experiment
With CH3I; NaH; ammonium chloride; In N,N-dimethyl-formamide; Under a nitrogen atmosphere, 1,4-bis(hydroxymethyl)cyclohexane (5 g, 0.0347 mol, 1:3 cis/trans mixture) in anhydrous DMF (20 ml) was added dropwise to NaH (1.6 g, 0.0366 mol, 55%) washed with hexane. The mixture was stirred at room temperature for 1/2 h, then CH3I (5 g, 0.0352 mol) dissolved in DMF (20 ml) was added dropwise. After the addition was complete the solution was stirred at room temperature for another 2 h; then NH4Cl solution was added, followed by a thorough extraction with ether. The ether extract was then dried over Na2SO4 under reduced pressure. Chromatography on silica gel, eluding with hexane/ethyl acetate (55/45), gave (4-methoxymethyl-cyclohexyl)methanol (1.8 g, 0.0113 mol) out of 4.1 g of residue.
 

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