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Chemical Structure| 502-44-3 Chemical Structure| 502-44-3

Structure of ε-Caprolactone
CAS No.: 502-44-3

Chemical Structure| 502-44-3

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Product Details of [ 502-44-3 ]

CAS No. :502-44-3
Formula : C6H10O2
M.W : 114.14
SMILES Code : O=C1OCCCCC1
MDL No. :MFCD00003267
InChI Key :PAPBSGBWRJIAAV-UHFFFAOYSA-N
Pubchem ID :10401

Safety of [ 502-44-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 502-44-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 30.13
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.

1.53
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

0.01
Log Po/w (WLOGP)?

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

1.1
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.

0.88
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

1.87
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.08

Water Solubility

Log S (ESOL):?

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

-0.55
Solubility 31.9 mg/ml ; 0.279 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.

-0.11
Solubility 87.8 mg/ml ; 0.769 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

-1.12
Solubility 8.68 mg/ml ; 0.076 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.

-6.99 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)

1.51

Application In Synthesis of [ 502-44-3 ]

* 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 [ 502-44-3 ]

[ 502-44-3 ] Synthesis Path-Downstream   1~9

  • 3
  • [ 6651-36-1 ]
  • [ 502-44-3 ]
  • [ 694-82-6 ]
  • [ 108-94-1 ]
  • 4
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 6665; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 5
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 8450; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 6
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 10166; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 8
  • [ 4224-62-8 ]
  • [ 502-44-3 ]
YieldReaction ConditionsOperation in experiment
95 parts by weight of the <strong>[4224-62-8]6-chlorocaproic acid</strong> were boiled with an aqueous solution of the equivalent amount of sodium hydroxide to obtain 69 parts by weight of epsilon-caprolactone. The 13C-NMR (100 MHz, internal standard CDCl3)of the synthesised epsilon-caprolactone was measured to obtain chemical shfts delta (ppm) as follows: epsilon-caprolactone: 13C-NMR (100 MHz, CDCl3) delta (ppm): 176.23, 69.30, 34.56, 29.35, 28.93, 22.98
  • 9
  • [ 502-44-3 ]
  • [ 4102-60-7 ]
  • (15Z,18Z)-6-[(9Z,12Z)-octadeca-9,12-dien-1-yl]tetracosa-15,18-diene-1,6-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Reaction 1 HGT5000 [0151] The intermediate compound (15Z, 18Z)-6-[ (9Z, 12Z)-octadeca-9, 12-dien-l- yl]tetracosa-15, 18-diene-l, 6-diol identified as compound (2) in Reaction 1 above was prepared as follows. To a lOOmL round bottom flask was added lOg (30mmol) of compound (1) (<strong>[4102-60-7]linoleyl bromide</strong>) and dry THF (20mL) under nitrogen. Magnesium powder (1.1 lg, 45mmol) was added to the stirred reaction solution followed by 2 drops of dibromoethane at room temperature. The reaction mixture was stirred at 50 C for 1 hour, and then diluted with dry THF (40mL). The reaction mixture was stirred another 15 minutes at room temperature. [0152] In a separate 250mL 3-neck flask was taken epsilon-caprolactone (1.44mL, 13.5mmol) in dry THF (20mL) under nitrogen. To the stirred solution was added the Grignard reagent through a cannula at 0 C. The resulting mixture was heated at 85 C for 3 hours. After cooling to room temperature, the reaction mixture was then quenched with NH4CI solution and extracted with dichloromethane (3 x lOOmL). The combined extracts were washed with brine (50mL), dried ( a2S04) and concentrated. The residue was purified twice by silica gel column chromatography (gradient elution from hexane to 3 :2 hexane/EA) to afford compound (2) as an oil. Yield: 5.46g (65%). XH NMR (301 MHz, CDC13) delta: 5.25 - 5.45 (m, 8H), 3.65 (m, 2H), 2.77 (t, J= 6.2 Hz, 4H), 1.95 - 2.1 (m, 8H), 1.2 - 1.70 (m, 50H), 0.88 (t, J= 6.9 Hz, 6H).
 

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