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Structure of 71432-55-8

Chemical Structure| 71432-55-8

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Product Details of [ 71432-55-8 ]

CAS No. :71432-55-8
Formula : C11H24N2O
M.W : 200.32
SMILES Code : CC(N=C(OC(C)(C)C)NC(C)C)C
MDL No. :MFCD06657672
InChI Key :FESDUDPSRMWIDL-UHFFFAOYSA-N
Pubchem ID :11041782

Safety of [ 71432-55-8 ]

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

Computational Chemistry of [ 71432-55-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.91
Num. rotatable bonds 5
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 62.6
TPSA ?

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

33.62 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.98
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

2.61
Log Po/w (WLOGP)?

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

2.56
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.

2.4
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

2.14
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.54

Water Solubility

Log S (ESOL):?

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

-2.4
Solubility 0.804 mg/ml ; 0.00402 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.

-2.97
Solubility 0.217 mg/ml ; 0.00108 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-2.63
Solubility 0.473 mg/ml ; 0.00236 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.

-5.67 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

2.0 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)

3.43

Application In Synthesis of [ 71432-55-8 ]

* 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 [ 71432-55-8 ]

[ 71432-55-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 71432-55-8 ]
  • [ 2799-07-7 ]
  • [ 76587-61-6 ]
  • 2
  • [ 494799-17-6 ]
  • [ 71432-55-8 ]
  • [ 879498-89-2 ]
YieldReaction ConditionsOperation in experiment
75% In dichloromethane; for 52h;Heating / reflux; Example 8; (2E)-3-{4-[({1-[({3-cycIohexyI-1-[2-(4-methylpiperazin-1-yI)-2- oxoethyl]-2-phenyl-1H-indol-6-yl}carbonyl)amino]cyclopentyl }carbonyl) amino]rhohenyI}acryli acid; Step 1; tert-butyl 3-cycIohexyl-1H-indole-6-carboxylate; A solution of 3-cycIohexenyl-1H -indole-6-carboxylic acid (1 eq., prepared as described in Example 1, Step 1) in dry DCM (0,19 M) was treated with tert-butyl N,N'-diisopropylimidocarbamate (2 eq.). The resulting clear solution was heated at reflux for 36 h. Addition of a further equivalent of isourea was required after 16 h to drive the reaction to completion. After cooling down the solvent was evaporated giving a residue that was purified by silica gel chromatography (Flashmaster Personal, PE: EtOAc, 30:1) affording tert-butyl 3-cyclohexyl-1H-indole-6-carboxylate (75percent)
58% In dichloromethane; for 19h;Heating / reflux; Step 4: tert-butyl S-cvclohexyl-lH-indole--carboxylate; 2 eq of tert-buty\\ N,N-diisopropylimidocarbamate (prepared according to literature precedent: Synthesis1979, 561) were added to a solution of 3-cyclohexyl-l//-indole-6-carboxylic acid (prepared as described in published International patent application WO2004087714) in CH2Cl2 (0.4 M) and the mixture heated at reflux under N2 for 16 h. A further 2.5 eq of tert-butyl N,N-diisopropylimidocarbamate were then added portionwise over 3 h, with heating being resumed after each addition. The reaction mixture was then filtered whilst hot through a pad of celite and the filtrate concentrated in vacuo. The residue was purified by flash chromatography (5percent EtOAc/PE) to afford the title compound (58 percent); MS (ES") m/z 298 (M-H)".
  • 3
  • [ 71432-55-8 ]
  • [ 2882-15-7 ]
  • [ 1226-02-4 ]
YieldReaction ConditionsOperation in experiment
7.2 g In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; DIC (12.1 mL, 77.8 mmol) was added to a mixture of CuCl (140 mg, 1.4 mmol) and tert-butanol (29.9 mL, 312.6 mmol) and the mixture was stirred at room temperature for 12 h. The volatile components were removed under reduced pressure. The solid was dissolved in THF (25 mL) and 5-methoxy-2-methyl-1H-indole-3-acetic acid (2) (7.0 g, 31.9 mmol) was added and the mixture stirred at room temperature for 2 h. The solvent was evaporated and the solid was purified by column chromatography with a mixture of hexanes (80-100 C) and ethyl acetate (3:1). The solvent was removed under reduced pressure to yield a white solid. Yield: 7.2 g (82%); elemental Anal. Calcd for C16H21NO3: C, 69.80; H, 7.69. Found: C, 69.57; H, 7.67; mp: 110-111 C; ESI MS (-) (CH3COCH3): m/z: 274.0 (100%, [M-H]-); 1H NMR (CDCl3, ppm): 7.75 (s, vbr, NHindole), 7.14 (d, 3JHH = 8 Hz, 1H, CHindole), 7.00 (d, 4JHH = 2 Hz, 1H, CHindole), 6.76 (dd, 3JHH = 8 Hz, 4JHH = 2 Hz, 1H, CHindole), 3.85 (s, 3H, OCH3), 3.54 (s, 2H, CH2), 2.39 (s, 3H, CH3), 1.43 (s, 9H, C(CH3)3); 13C{1H} NMR (CDCl3, ppm): 171.4 (COO), 154.0 (CindoleO), 133.5 (Cindole), 130.2 (Cindole), 129.1 (Cindole), 110.9 (CindoleH), 110.9 (CindoleH), 105.0 (Cindole), 100.6 (CindoleH), 80.5 (C(CH3)3), 55.9 (OCH3), 31.9 (CH2), 28.1 (C(CH3)3), 11.9 (CH3); IR (selected, KBr, cm-1): = 3342 (s, nu(N-H)), 3005 (w), 2980 (w), 2965 (w), 2914 (w), 2837 (w), 2047 (w), 1722 (s, nu(CO)).
  • 4
  • [ 71432-55-8 ]
  • [ 2592-18-9 ]
  • tert-butyl 2-(tert-butoxycarbonylamino)-3-hydroxybutanoate [ No CAS ]
 

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