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Chemical Structure| 51260-39-0

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Product Details of [ 51260-39-0 ]

CAS No. :51260-39-0
Formula : C4H6O3
M.W : 102.09
SMILES Code : O=C1OC[C@H](C)O1
MDL No. :MFCD00798264
InChI Key :RUOJZAUFBMNUDX-VKHMYHEASA-N
Pubchem ID :2734444

Safety of [ 51260-39-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 51260-39-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 21.99
TPSA ?

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

35.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.27
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

-0.41
Log Po/w (WLOGP)?

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

0.54
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.

-0.38
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

0.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.37

Water Solubility

Log S (ESOL):?

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

-0.21
Solubility 62.3 mg/ml ; 0.61 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.

0.13
Solubility 137.0 mg/ml ; 1.34 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-0.16
Solubility 70.5 mg/ml ; 0.69 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.

-7.21 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

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)

2.2

Application In Synthesis of [ 51260-39-0 ]

* 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 [ 51260-39-0 ]

[ 51260-39-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 51260-39-0 ]
  • [ 16606-55-6 ]
YieldReaction ConditionsOperation in experiment
34.2% With C126H91CoN12O10; tetrabutyl-ammonium chloride In dichloromethane at 25℃; for 96 h; Autoclave General procedure: All reactions were conducted in a 100 mL stainless steel autoclave equipped with a magnetic stir bar, and submerged in anoil bath. The required catalyst, tetrabutylammonium chloride (TBAC) as the co‐catalyst, epoxide, and CH2Cl2 were added tothe reactor in turn. The reactor was then charged with CO2 and vented three times, and finally pressurized with CO2 to 1.0 MPa. The contents were then stirred at room temperature for an established period that depended on the selected substrate and catalyst, after which the reactor was carefully discharged to atmospheric pressure. The yield of cyclic carbonate was determinedby the subtraction method or by comparison betweenthe integral areas obtained by 1H NMR spectroscopy for thecyclic carbonate and epoxide.
31.6% With C126H91CoN12O10; tetrabutyl-ammonium chloride In dichloromethane at 25℃; for 96 h; Autoclave General procedure: All reactions were conducted in a 100 mL stainless steel autoclave equipped with a magnetic stir bar, and submerged in anoil bath. The required catalyst, tetrabutylammonium chloride (TBAC) as the co‐catalyst, epoxide, and CH2Cl2 were added tothe reactor in turn. The reactor was then charged with CO2 and vented three times, and finally pressurized with CO2 to 1.0 MPa. The contents were then stirred at room temperature for an established period that depended on the selected substrate and catalyst, after which the reactor was carefully discharged to atmospheric pressure. The yield of cyclic carbonate was determinedby the subtraction method or by comparison betweenthe integral areas obtained by 1H NMR spectroscopy for thecyclic carbonate and epoxide.
38.8 % ee at 25℃; for 25 h; Autoclave General procedure: A solution of freshly prepared SalenCo(III)Y (0.1 mmol) andepoxide (100 mmol) was introduced into a 100 mL stainless-steelautoclave, which was purged three times and charged with CO2to 1.2 MPa. The reaction mixture was stirred at room temperature.When the pressure of reactor was fall down to a presetting value, itwas then vented carefully. After removing the excess epoxide, theresidue was weighed to measure the conversion of epoxide, chiralcyclic carbonate (R = Me, Et, CH2Cl) was distilled under vacuum as asa colorless liquid or it (R = Ph, PhOCH2) was obtained by columnchromatography through a short silica–gel column to yield whitesolid product (ethyl acetate/petroleum ether = 5:1).
References: [1] Dalton Transactions, 2013, vol. 42, # 27, p. 9930 - 9937.
[2] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003.
[3] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003.
[4] Journal of the American Chemical Society, 2004, vol. 126, # 12, p. 3732 - 3733.
[5] Chemical Communications, 2004, # 14, p. 1622 - 1623.
[6] Tetrahedron Letters, 2007, vol. 48, # 2, p. 297 - 300.
[7] Tetrahedron Letters, 2008, vol. 49, # 46, p. 6589 - 6592.
[8] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1325 - 1332.
[9] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1325 - 1332.
[10] Green Chemistry, 2009, vol. 11, # 7, p. 935 - 938.
[11] Green Chemistry, 2009, vol. 11, # 7, p. 935 - 938.
[12] Science China Chemistry, 2011, vol. 54, # 7, p. 1044 - 1050.
[13] Science China Chemistry, 2011, vol. 54, # 7, p. 1044 - 1050.
[14] Catalysis Science and Technology, 2013, vol. 3, # 10, p. 2661 - 2667.
[15] Journal of Molecular Catalysis A: Chemical, 2016, vol. 411, p. 34 - 39.
[16] RSC Advances, 2016, vol. 6, # 4, p. 3243 - 3249.
[17] Chemical Communications, 2017, vol. 53, # 79, p. 10930 - 10933.
[18] Chemical Communications, 2017, vol. 53, # 79, p. 10930 - 10933.
[19] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003.
  • 2
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 51260-39-0 ]
  • [ 15448-47-2 ]
  • [ 16606-55-6 ]
YieldReaction ConditionsOperation in experiment
66.7 % ee at 25℃; for 8 h; Autoclave General procedure: Catalyst of (S,R,R,S)-ZSS-2b (631 mg, 0.1 mmol), cocatalyst of tetrabutylammonium fluoride (TBAF, 0.0522 g, 0.2 mmol), and racemic propylene oxide (PO, 7 mL, 100 mmol) were introduced into a 100-mL stainless steel autoclave to form a brown solution. The reactor was purged thrice with carbon dioxide, and charged it to 0.8 MPa. Then, the asymmetric catalytic reaction took place at room temperature. After some time, the pressure in the reactor decreased to an expected value, and it was vented to terminate the reaction. After removing the unreacted epoxide, chiral cyclic carbonate (R=Me, Et, CH2Cl), weighed to calculate the yield of cyclic carbonate, was distilled under vacuum as a colorless liquid or it (R=Ph, PhOCH2) was obtained by column chromatography through a short silica gel column (ethyl acetate:petroleum ether = 5:1).
References: [1] Tetrahedron Asymmetry, 2008, vol. 19, # 16, p. 1947 - 1953.
[2] Catalysis Communications, 2016, vol. 81, p. 50 - 53.
  • 3
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 51260-39-0 ]
  • [ 16088-62-3 ]
  • [ 16606-55-6 ]
YieldReaction ConditionsOperation in experiment
66.8 % ee at 0℃; for 8 h; Autoclave General procedure: Catalyst of (S,R,R,S)-ZSS-2b (631 mg, 0.1 mmol), cocatalyst of tetrabutylammonium fluoride (TBAF, 0.0522 g, 0.2 mmol), and racemic propylene oxide (PO, 7 mL, 100 mmol) were introduced into a 100-mL stainless steel autoclave to form a brown solution. The reactor was purged thrice with carbon dioxide, and charged it to 0.8 MPa. Then, the asymmetric catalytic reaction took place at room temperature. After some time, the pressure in the reactor decreased to an expected value, and it was vented to terminate the reaction. After removing the unreacted epoxide, chiral cyclic carbonate (R=Me, Et, CH2Cl), weighed to calculate the yield of cyclic carbonate, was distilled under vacuum as a colorless liquid or it (R=Ph, PhOCH2) was obtained by column chromatography through a short silica gel column (ethyl acetate:petroleum ether = 5:1).
References: [1] Catalysis Communications, 2016, vol. 81, p. 50 - 53.
  • 4
  • [ 75-56-9 ]
  • [ 51260-39-0 ]
  • [ 15448-47-2 ]
  • [ 16088-62-3 ]
  • [ 16606-55-6 ]
References: [1] Organic Letters, 2006, vol. 8, # 20, p. 4401 - 4404.
  • 5
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  • [ 15448-47-2 ]
  • [ 16088-62-3 ]
  • [ 16606-55-6 ]
References: [1] Organic Letters, 2006, vol. 8, # 20, p. 4401 - 4404.
 

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