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Chemical Structure| 61010-04-6 Chemical Structure| 61010-04-6

Structure of 61010-04-6

Chemical Structure| 61010-04-6

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Product Details of [ 61010-04-6 ]

CAS No. :61010-04-6
Formula : C8H9ClO2
M.W : 172.61
SMILES Code : O/C=C1C(Cl)=C(C=O)CCC/1
MDL No. :MFCD01863678

Safety of [ 61010-04-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H303-H314
Precautionary Statements:P201-P202-P280-P210-P240-P264-P270-P301+P310-P330-P370+P378-P403+P233-P405-P501
Class:4.1(8)
UN#:2925
Packing Group:

Computational Chemistry of [ 61010-04-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.38
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 44.08
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.72
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

1.14
Log Po/w (WLOGP)?

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

2.3
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.

0.87
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

2.22
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.65

Water Solubility

Log S (ESOL):?

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

-1.56
Solubility 4.73 mg/ml ; 0.0274 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.

-1.52
Solubility 5.24 mg/ml ; 0.0304 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

-1.53
Solubility 5.07 mg/ml ; 0.0294 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.

-6.54 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

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)

2.99

Application In Synthesis of [ 61010-04-6 ]

* 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 [ 61010-04-6 ]

[ 61010-04-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 61010-04-6 ]
  • [ 20205-29-2 ]
  • [ 207399-07-3 ]
YieldReaction ConditionsOperation in experiment
96% In butan-1-ol; benzene; at 160℃; for 10h;Inert atmosphere; la (500 mg, 2.9 mmol, lequiv) and lb (1.91g, 5.81 mmol, 2 equiv) were dissolved in n-butanol (BuOH)-benzene (7:3) under N2 atmosphere, and refluxed at 160 C for 10 hours with a Dean-Stark condenser. Afterwards, the solvent was evaporated, and the resulting green solid was washed with Et20 and purified by flash chromatography (DCM-MeOH, 50:1) to obtain 1 as a green solid (1.8 g, 96%). 1H- NMR (300 MHz, CDC13) 5=1.06 (t, 6H, J=7.5 Hz), 1.31 (m, 4H), 1.64 (s, 12H), 1.95 (m, 2H), 2.73 (m, 4H), 4.15 (t, 4H, J=6.9Hz), 6.23 (d, 2H, J=14.2 Hz), 7.15-7.72 (m, 8H), 8.19 (d, 2H, J=13.8 Hz). tR: 5.64 min, ESI m/z (C36H44C1N2+), calc: 539.4; found: 539.1.
85.3% With sodium acetate; In toluene;Inert atmosphere; Reflux; Dean-Stark; Compound 3 (0.5 g, 2.9 mmol) and compound 4 (1.91 g, 5.81 mmol) were dissolved in BuOH-toluene (25 mL, 7:3, v:v) under Ar, and the solution was refluxed overnight in a 100-mL flask with three necks installed with a Dean-Stark condenser to remove generated water. Then, all solvents were removed under vacuum and the residual solid was purified with a flash chromatography (DCM:MeOH, 50:1 to 20:1, v:v) to give compound 4 (IR780, 1.6 g, 85.3%) as a dark green solid.
71.17% In cyclohexane; butan-1-ol; at 100℃; for 10h;Inert atmosphere; Starting material A (0.86 g, 5 mmol), starting material B (3.29 g, 10 mmol),Add 28 mL of n-butanol and 12 mL of cyclohexaneIn a 100 mL round bottom flask, replace N2 three times with vacuum.The temperature was raised to 100 C and refluxed for 10 hours.After cooling the reaction solution to room temperature,A large amount of metallic luster green solid is produced in the system, suction filtration, petroleum ether,The filter cake was rinsed with ethyl acetate to give 2.37 g of a gold-green solid powder.The yield was 71.17%.
In toluene; butan-1-ol; at 120℃; for 12h;Darkness; Under ice bath conditions, POCl3 (10.5 mL, 115 mmol)Methylene chloride solution (5 mL) was slowly added to DMF (20 mL, 258 mmol)The mixture was mixed with dichloromethane (15 mL) and stirred for 0.5 h.Cyclohexanone (5 g, 50 mmol) was added dropwise to the solution.The mixed solution was refluxed for 6 hours and poured into an ice water mixture.After 12 hours, the resulting yellow crystals were filtered to give a yellow solid powder, Compound a.Dissolve in 50ml acetonitrile at room temperature2,3,3-trimethylhydrazine(2g, 12.5mmol) and propyl iodide(10.6g, 62mmol),Stir at 85 C for 15 h in the dark.The solvent was recrystallized from anhydrous diethyl ether to give a purple powder, Compound b.Compound a (0.52 g, 3 mmol, 1 equiv.), b (1.97 g, 6 mmol, 2 equiv.)The mixed solution of butanol and toluene (20 mL, 3:7, v/v) was stirred at 120 C for 12 h in the dark.After cooling to room temperature, the solvent was evaporated under reduced pressure to give a crude product, which was crystallised twice from diethyl ether.A green powder, Cy7-Cl, was obtained.

 

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Technical Information

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[ 61010-04-6 ]

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