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Chemical Structure| 6092-54-2 Chemical Structure| 6092-54-2

Structure of 6092-54-2

Chemical Structure| 6092-54-2

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Product Details of [ 6092-54-2 ]

CAS No. :6092-54-2
Formula : C7H13ClO2
M.W : 164.63
SMILES Code : O=C(Cl)OCCCCCC
MDL No. :MFCD00000651
InChI Key :KIWBRXCOTCXSSZ-UHFFFAOYSA-N
Pubchem ID :22466

Safety of [ 6092-54-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H314
Precautionary Statements:P261-P270-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Class:6.1(8)
UN#:3277
Packing Group:

Computational Chemistry of [ 6092-54-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.86
Num. rotatable bonds 6
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 42.23
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.62
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

3.48
Log Po/w (WLOGP)?

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

2.94
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.

1.96
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

2.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.62

Water Solubility

Log S (ESOL):?

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

-2.66
Solubility 0.363 mg/ml ; 0.0022 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.

-3.71
Solubility 0.0318 mg/ml ; 0.000193 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

-2.59
Solubility 0.426 mg/ml ; 0.00259 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.

-4.83 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

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)

1.81

Application In Synthesis of [ 6092-54-2 ]

* 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.

  • Upstream synthesis route of [ 6092-54-2 ]
  • Downstream synthetic route of [ 6092-54-2 ]

[ 6092-54-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 75-75-2 ]
  • [ 6092-54-2 ]
  • [ 872728-81-9 ]
References: [1] Patent: WO2010/45900, 2010, A1, . Location in patent: Page/Page column 10.
  • 2
  • [ 75-75-2 ]
  • [ 6092-54-2 ]
  • [ 872728-81-9 ]
YieldReaction ConditionsOperation in experiment
35.1 g
Stage #1: With potassium carbonate In water; acetone at 5℃; for 1 h;
Stage #2: at 0 - 20℃; for 1 h;
By embodiments 2 - 4 prepared in the target product is 40g adding 3000 ml glass reaction in the bottle, sequentially adding potassium carbonate 33.0g, water 220 ml, acetone 350 ml, stirring the temperature to 5 °C, continuing to stir 10 minutes, slowly instillment chlorine formic acid oneself ester 16.0g, after finishing dropping to continue to 5 °C stirring 1 hours, to the reaction solution is added in dichloromethane 1600 ml, up to 28 °C extracting the organic layer, the saturated salt water for 1600 ml washing, the organic layer is dried with anhydrous sodium sulfate, vacuum concentrated solvent to obtain yellowish liquid. Dichloromethane is used for 80 ml dissolved concentrated residual liquid, adding 1000 ml in the reaction flask, lowering the temperature to 0 °C, in 0 °C slow the instillment uses acetone 640 ml of dissolved methanesulfonic acid 7.7g mixed solution, after the completion of the dropping the temperature to room temperature stirring 1 hour, filtering, dichloromethane 320 ml washing, in 40 °C vacuum drying 5 hours, to obtain 35.1g white compound A, HPLC analysis for 99.789percent
References: [1] Patent: CN106397403, 2017, A, . Location in patent: Paragraph 0063; 0064; 0065; 0066; 0067.
  • 3
  • [ 75-75-2 ]
  • [ 6092-54-2 ]
  • [ 872728-81-9 ]
References: [1] Patent: WO2010/45900, 2010, A1, . Location in patent: Page/Page column 11.
 

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