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Chemical Structure| 59032-71-2 Chemical Structure| 59032-71-2

Structure of 59032-71-2

Chemical Structure| 59032-71-2

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Product Details of [ 59032-71-2 ]

CAS No. :59032-71-2
Formula : C11H18O3
M.W : 198.26
SMILES Code : O=C(C1(CC)CCC(CC1)=O)OCC
MDL No. :N/A
InChI Key :DHQTYJFKOHBZOM-UHFFFAOYSA-N
Pubchem ID :21911982

Safety of [ 59032-71-2 ]

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

Computational Chemistry of [ 59032-71-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 54.1
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.34
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

1.34
Log Po/w (WLOGP)?

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

2.09
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.

1.49
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

2.66
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.98

Water Solubility

Log S (ESOL):?

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

-1.65
Solubility 4.44 mg/ml ; 0.0224 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.

-1.85
Solubility 2.78 mg/ml ; 0.014 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

-2.7
Solubility 0.394 mg/ml ; 0.00199 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.

-6.56 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)

2.09

Application In Synthesis of [ 59032-71-2 ]

* 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 [ 59032-71-2 ]

[ 59032-71-2 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 4973-66-4 ]
  • [ 59032-71-2 ]
  • [ 72137-33-8 ]
  • 2
  • ethyl 8-ethyl-1,4-dioxaspiro[4.5]decane-8-carboxylate [ No CAS ]
  • [ 59032-71-2 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride; water; In acetone; at 20℃; for 16h; To a stirred solution of compound D22-1 (2.07 g, 8.54 mmol) in acetone (60 mL) was added aqueous HC1 (2 M solution, 40 mL) at room temperature. The mixture was stirred at the same temperature for 16 h. Acetone was removed under reduced pressure. The residue was basified with aqueous NaHC03 solution and extracted with DCM (2 x 30 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to give compound D22-2 (1.85 g, 99%) as a colorless gum.
  • 5
  • [ 59032-71-2 ]
  • ethyl (1,4-cis)-1-ethyl-4-hydroxycyclohexanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In methanol; at 0℃; for 0.583333h; [0464] To a solution of 1.65 g of <strong>[59032-71-2]ethyl 1-ethyl-4-oxocyclohexanecarboxylate</strong> (which was prepared by the method as described in J. Am. Chem. Soc.,1979, 101, 6414-6420) in 17 ml of methanol, 250 mg of sodium borohydide was added at 0 C., followed by 35 minutes' stirring at the same temperature. After adding water to the reaction liquid, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried on anhydrous magnesium sulfate, and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (ethyl acetate/hexane=1/3) to provide 648 mg of the title compound.
  • 6
  • [ 17159-79-4 ]
  • [ 59032-71-2 ]
  • 7
  • [ 1489-97-0 ]
  • [ 59032-71-2 ]
  • 8
  • [ 871115-32-1 ]
  • [ 59032-71-2 ]
  • tert-butyl 4-amino-4-[[(4-ethoxycarbonyl-4-ethyl-cyclohexyl)amino]methyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Dissolve tert-butyi 4-amino-4-(arninomethyl)piperidine- 1 -carboxylate (1.4 g, 5.7 mmol), ethyl I -ethyi-4-oxo-cyclohexanecarboxy]ate (1.4, 5.7 mmo]) and acetic acid (0.3 mL, 5,7 mmol) in DCM (5.7 mL) at it After 30 mm, add sodium triacetoxyborohydride (1.6 g, 7.5 mmol) and stir the mixture at rt for 18 hrs. Dilute the mixture with DCM (2()() rnL), and wash with saturated aqueous solution of NaHCO3 (100 mL). Dry the organic phase over Na2SO4 filter, and remove the solvent from the filtrate to give the title compound as a brown oil in quantitative yield (mixture of cis/trans isomers). This material can be used in the next step without any thrther purification. ES/MS rn/z 412 (M-t-H).
  • 9
  • [ 871115-32-1 ]
  • [ 59032-71-2 ]
  • tert-butyl 3-(4-ethoxycarbonyl-4-ethyl-cyclohexyl)-2-oxo-1,3,8-triazaspiro[4,5]decane-8-carboxylate [ No CAS ]
 

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Technical Information

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