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Chemical Structure| 2523-55-9 Chemical Structure| 2523-55-9

Structure of trans-4-Methylcyclohexanamine
CAS No.: 2523-55-9

Chemical Structure| 2523-55-9

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Product Details of [ 2523-55-9 ]

CAS No. :2523-55-9
Formula : C7H15N
M.W : 113.20
SMILES Code : N[C@H]1CC[C@H](C)CC1
English Name :trans-4-Methylcyclohexylamine
MDL No. :MFCD06411232
InChI Key :KSMVBYPXNKCPAJ-UHFFFAOYSA-N
Pubchem ID :80604

Safety of [ 2523-55-9 ]

Computational Chemistry of [ 2523-55-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 36.36
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.

1.93
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

1.53
Log Po/w (WLOGP)?

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

1.52
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

1.32
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.

-1.51
Solubility 3.53 mg/ml ; 0.0312 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.

-1.69
Solubility 2.34 mg/ml ; 0.0206 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

-1.06
Solubility 9.95 mg/ml ; 0.0879 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.

-5.9 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<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)

1.95

Application In Synthesis of [ 2523-55-9 ]

* 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 [ 2523-55-9 ]

[ 2523-55-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2523-55-9 ]
  • [ 175357-98-9 ]
  • [ 845522-46-5 ]
YieldReaction ConditionsOperation in experiment
78% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;
  • 2
  • [ 318515-70-7 ]
  • [ 2523-55-9 ]
  • [ 93479-97-1 ]
YieldReaction ConditionsOperation in experiment
95% In toluene Heating / reflux; 2 Example 2: Preparation of Glimepiride (Formula I, Grp1=D and Grp2= R) In a reaction vessel, 80 gm of carbamate of Formula IX, 27.2 gm trans 4-methylcyclohexyl amine, 11.5 gm 4-dimethylamino pyridine and 1.6 lit. toluene was taken and the mixture was heated to reflux and toluene was distilled out maintaining total volume of the reaction constant. After completion of reaction the mass was cooled to 25 to 30C, to precipitate the Glimepiride, filtered and washed with 800 ml of toluene. The filtered material was dried to get 88 gm (95% yield) of Glimepiride (purity 99.5%) 80 gm of Glimepiride, obtained as per the above example, was stirred with 800 ml of acetone at reflux temperature for 30 minutes and cooled to 25 to 30C, filtered, washed with 400 mi acetone. The filtered material was dried to weigh 75 gm Glimepiride of 99.7% purity (by HPLC) and impurity of sulphonamide (Vl) and carbamate (IX) 0.2 and 0.05 % respectively. Melting point: 207 to 211C.
95% With dmap In toluene Heating / reflux; 2 In a reaction vessel, 80 g of carbamate of Formula IX, 27.2 g trans-4-methylcyclohexyl amine, 11.5 g 4-dimethylamino pyridine, and 1.6 L of toluene were mixed and heated to reflux. The toluene was distilled out, while maintaining total volume of the reaction constant. After completion of the reaction, the mass was cooled to 25 to 30° C. to precipitate the glimepiride which was filtered and washed with 800 mL of toluene. The filtered material was dried to get 88 gm (95% yield) of glimepiride (purity 99.5%). 80 g of glimepiride (obtained as above) was stirred with 800 mL of acetone at reflux temperature for 30 minutes, cooled to 25 to 30° C., filtered, and washed with 400 mL acetone. The filtered material was dried to produce 75 g glimepiride of 99.7% purity (by HPLC) with impurities of sulphonamide (Formula VI) and carbamate (Formula IX) at 0.2 and 0.05%, respectively. The melting point of the final product was 207 to 211° C.
  • 3
  • [ 127094-57-9 ]
  • [ 2523-55-9 ]
  • [ 2598889-19-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃;
  • 4
  • [ 2523-55-9 ]
  • [ 585-36-4 ]
  • [ 2488676-18-0 ]
YieldReaction ConditionsOperation in experiment
52% With 1,4-diaza-bicyclo[2.2.2]octane; aluminium(III) triflate; chloropyridinecobaloxime(III); C32H24N4 In acetonitrile at 25℃; for 48h; Inert atmosphere; Irradiation;
 

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