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Chemical Structure| 63126-47-6 Chemical Structure| 63126-47-6

Structure of 63126-47-6

Chemical Structure| 63126-47-6

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Product Details of [ 63126-47-6 ]

CAS No. :63126-47-6
Formula : C6H13NO
M.W : 115.17
SMILES Code : COC[C@H]1NCCC1
MDL No. :MFCD00010408
InChI Key :CHPRFKYDQRKRRK-LURJTMIESA-N
Pubchem ID :671217

Safety of [ 63126-47-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 63126-47-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 36.64
TPSA ?

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

21.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.98
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

0.2
Log Po/w (WLOGP)?

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

0.0
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.

0.21
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

1.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.7

Water Solubility

Log S (ESOL):?

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

-0.55
Solubility 32.6 mg/ml ; 0.283 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.

-0.21
Solubility 71.8 mg/ml ; 0.623 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

-1.29
Solubility 5.95 mg/ml ; 0.0516 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

Low
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

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.

-6.86 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)

1.69

Application In Synthesis of [ 63126-47-6 ]

* 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 [ 63126-47-6 ]

[ 63126-47-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 63126-47-6 ]
  • [ 132898-96-5 ]
  • [ 220509-74-0 ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0℃; for 1.5h; Step 2: 5-[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold suspension of <strong>[132898-96-5]2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride</strong> (5.28 g, 21.5 mmol) in a 1:1 mixture of THF:CHCl3 (254 mL) was added drop-wise via syringe pump a solution of (S)-(+)-2-(methoxymethyl)-pyrrolidine (3.45 mL, 28.0 mmol, 1.3 eq) (Aldrich) and N,N-diisopropylethylamine (7.49 mL, 43 mmol, 2 eq) in CHCl3 (42 mL) over a period of 70 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring an additional 20 minutes the mixture was concentrated. The residue was flash chromatographed (Biotage KP silica gel, 98/2 CH2Cl2/CH3OH) to give the title compound as a dark greenish-yellow foam (6.48 g. 93% yield). NMR (400 MHz, DMSO-d6): consistent MS: (API-ES-) m/z 323[M-H].
  • 2
  • [ 63126-47-6 ]
  • [ 132898-96-5 ]
  • [ 220509-85-3 ]
YieldReaction ConditionsOperation in experiment
63.8% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0℃; for 2.5h; Step 1: 5-[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a stirred cold suspension of 2,3-dioxo-2,3-dihydro-1H-indol-5-sulfonyl chloride (5.00 g, 20.4 mmol) in a 1:1 mixture of THF: CHCl3 (140 mL) was added dropwise, via syringe pump, a solution of N,N-diisopropylethylamine (7.11 mL, 40.8 mmol, 2 eq) and (R)-2-(Methoxymethyl)pyrrolidine (3.27 mL, 26.5 mmol, 1.3 eq) in CHCl3 (60 mL) over a period of 1.5 hours with cooling in an ice bath. After stirring an additional 1 h, the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 95/5 CH2Cl2/CH3OH followed by a second chromatography on silica gel eluding with EtOAc to give 4.21 g (63.8%) of the title compound. NMR (400 MHz, DMSO-d6): consistent.
  • 3
  • [ 13195-50-1 ]
  • [ 63126-47-6 ]
  • [ 536-74-3 ]
  • (E)-1-[2-(5-nitrothien-2-yl)-1-phenylvinyl]-(2R)-methoxymethylpyrrolidine [ No CAS ]
  • 4
  • [ 516-09-6 ]
  • [ 63126-47-6 ]
  • [ 1035419-85-2 ]
YieldReaction ConditionsOperation in experiment
81% With toluene-4-sulfonic acid; In toluene; at 130℃;Heating / reflux; Example 14: Synthesis of 4-(2(S)-Methoxymethyl-pyrrolidin-1-yl)-3-methyl-5H-furan-2-one.; [Show Image] p-Toluenesulphonic acid monohydrate (15.00 mg, 0.08 mmol) and then (S)-2-methoxymethyl)pyrrolidine (100.00 mg, 0.87 mmol) were added into a mixture of <strong>[516-09-6]4-hydroxy-3-methyl-5H-furan-2-one</strong> (90.00 mg, 0.80 mmol) in dry toluene (5 ml). The reaction mixture was stirred wildly at reflux temperature (130C) and it became a brown transparent solution. Stirring was kept at 130C overnight. The solvent was evaporated in vacuo and the residue was purified by radial chromatography using AcOEt/MeOH (from 100/0 to 100/10 in a 2% polarity increment) to yield 136.70 mg (81%) of 4-(2(S)-Methoxymethyl-pyrrolidin-1-yl)-3-methyl-5H-furan-2-one as a yellow oil. 1H-RMN (400 MHz, CDCl3): 4.89 (d, 1 H, J=15 Hz, 5-CH2 furanone); 4.53 (d, 1 H, J=15 Hz, 5-CH2 furanone); 3.97 (m, 1 H, 2-CH pyrrolidinyl); 3.57 (m, 1 H, 5-CH2 pyrrolodinyl); 3.42 (m, 1 H, 5-CH2 pyrrolodinyl); 3.32 (m and s, 4H, 2-CH2-OMe pyrrolidinyl and O-CH3 pyrrolodinyl); 3.25 (m, 1 H, 2-CH2-OMe pyrrolidinyl); 2.01-1.93 (m, 4H, 3-CH2 pyrrolodinyl, 4-CH2 pyrrolodinyl) 1.92 (s, 3H, CH3 furanone). 13C-RMN (100 MHz, CDCl3): 177.17 (2-CO furanone); 160.31 (4-C=N furanone); 88.70 (3-C(Me)= furanone); 74.47 (2-CH2-Ome, pyrrolidinyl); 66.64 (5-CH2 furanone); 59.29 (O-CH3 pyrrolidinyl); 58.77 (2-CH pyirrolidinyl); 48.66 (5-CH2 pyrrolidinyl); 28.01 (3-CH2 pyrrolidinyl); 22.92 (4-CH2, pyrrolidinyl); 8.98 (3-CH3 furanone).
 

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