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Structure of 25125-21-7

Chemical Structure| 25125-21-7

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Product Details of [ 25125-21-7 ]

CAS No. :25125-21-7
Formula : C6H10O
M.W : 98.14
SMILES Code : OCC1CC=CC1
MDL No. :MFCD04038630
InChI Key :ADLKZHGHNJBOOC-UHFFFAOYSA-N
Pubchem ID :1514122

Safety of [ 25125-21-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H412
Precautionary Statements:P264-P270-P273-P301+P312+P330-P501

Computational Chemistry of [ 25125-21-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.67
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 29.53
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.65
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

0.95
Log Po/w (WLOGP)?

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

0.94
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.

1.0
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

1.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.14

Water Solubility

Log S (ESOL):?

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

-0.98
Solubility 10.3 mg/ml ; 0.104 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.

-0.96
Solubility 10.7 mg/ml ; 0.109 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

-0.32
Solubility 47.4 mg/ml ; 0.483 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.

-6.22 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

1.0 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)

2.96

Application In Synthesis of [ 25125-21-7 ]

* 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 [ 25125-21-7 ]

[ 25125-21-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 21622-01-5 ]
  • [ 25125-21-7 ]
YieldReaction ConditionsOperation in experiment
84% To a cold (-78 C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at -78 C.under argon for 4 h. Then the reaction solution was allowed towarm to 0 C., and 2.5 mE of water, 2.5 mE of 15% NaOH,and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4),filtered, concentrated and dried in vacuo to give 4.294 g(84%) of 704 as a pale yellow liquid. ‘H NMR (400 MHz, CDC13) ö 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).
With sodium hydroxide; In water; Step A : Preparation of 3-cyclopentenylmethanol 0.78 mol (109.45 g) of 3-cyclopentenylcarboxylic acid ethyl ester dissolved in 400 ml of anhydrous ether are added dropwise to a stirred suspension of 24 g of lithium aluminum hydride (0.7 mmol) in 500 ml of anhydrous ether. The reaction mixture is stirred at 20C for 3 hours and hydrolized by careful addition of 24 ml of water, 24 ml of 15% aqueous sodium hydroxide and three times 24 ml of water. The white precipitate is discarded by filtration and the filtrate is washed twice with brine, dried over sodium sulfate, filtered and evaporated to give 67.5 g of the product 3-cyclopentenylmethanol (88% yield) which is used in the next step without further purification.
  • 2
  • [ 1354961-13-9 ]
  • [ 25125-21-7 ]
  • tert-butyl 5-chloro-4-(cyclopent-3-en-1-ylmethoxy)-2-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With caesium carbonate; In dimethyl sulfoxide; at 80℃; for 10h; A mixture of cyclopent-3-enylmethanol (0.9 g, 9.2 mmol) , tert-butyl 5-chloro-2, 4-difluorobenzoate (2.3 g, 9.3 mmol) and cesium carbonate (6.0 g, 18.4 mmol) in DMSO (20 mL) was stirred at 80 for 10 h. The reaction mixture was diluted with EtOAc (50 mL) and brine (100 mL) . The organic layer was washed by brine (30 mL×3) , dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column (petroleum ether) to afford the title compound as a white solid (2.1 g, 70)
 

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Technical Information

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