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Chemical Structure| 645-67-0

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Product Details of [ 645-67-0 ]

CAS No. :645-67-0
Formula : C8H14O3
M.W : 158.20
SMILES Code : O=C(C)CCC(OCCC)=O
MDL No. :MFCD16041935
Boiling Point : No data available
InChI Key :QOSMNYMQXIVWKY-UHFFFAOYSA-N
Pubchem ID :221069

Safety of [ 645-67-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 645-67-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 6
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 42.05
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.16
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

0.6
Log Po/w (WLOGP)?

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

1.31
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.

0.97
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

1.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.32

Water Solubility

Log S (ESOL):?

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

-0.8
Solubility 24.9 mg/ml ; 0.157 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.

-1.08
Solubility 13.0 mg/ml ; 0.0823 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

-1.9
Solubility 2.0 mg/ml ; 0.0126 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.

-6.84 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)

1.77

Application In Synthesis of [ 645-67-0 ]

* 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 [ 645-67-0 ]
  • Downstream synthetic route of [ 645-67-0 ]

[ 645-67-0 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 71-23-8 ]
  • [ 123-76-2 ]
  • [ 645-67-0 ]
YieldReaction ConditionsOperation in experiment
88 %Chromat. With caesium carbonate In toluene for 2 h; General procedure: Esterification of levulinic acid was carried out in a 50mL round bottom flask equipped with a reflux condenser. In a typical catalytic reaction the catalyst (40mg) was added to a mixture of levulinic acid and ethanol with the molar ratio of LA: alcohol=1:8 (ethanol acts as reagent cum solvent) and the mixture was magnetically stirred at 333K for 2h. A portion of the reaction mixture was separated after the scheduled reaction time through filtration and the filtrate was then analyzed through the gas chromatography (GC) equipped with a flame-ionized detector and a capillary column. All compounds were characterized on the basis of their spectroscopic data (1H NMR) and by comparison with those reported in the literature.
References: [1] RSC Advances, 2016, vol. 6, # 3, p. 2106 - 2111.
[2] Journal of the American Chemical Society, 1930, vol. 52, p. 4883.
[3] Journal of the American Chemical Society, 1933, vol. 55, p. 3393.
[4] Patent: US2029412, 1934, , .
[5] Journal fuer Praktische Chemie (Leipzig), 1955, vol. &lt;4&gt; 1, p. 153,154.
[6] Patent: WO2010/102203, 2010, A2, . Location in patent: Page/Page column 26-27.
[7] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791.
[8] Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 30 - 38.
[9] Applied Catalysis A: General, 2017, vol. 547, p. 237 - 247.
[10] Catalysis Today, 2018, vol. 309, p. 253 - 262.
  • 2
  • [ 71-23-8 ]
  • [ 492-62-6 ]
  • [ 645-67-0 ]
References: [1] Patent: CN103408422, 2016, B, . Location in patent: Paragraph 0043; 0044.
  • 3
  • [ 98-00-0 ]
  • [ 71-23-8 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2014, vol. 16, # 3, p. 1436 - 1443.
[2] ChemCatChem, 2014, vol. 6, # 11, p. 3080 - 3083.
[3] Russian Journal of Applied Chemistry, 2007, vol. 80, # 10, p. 1687 - 1690.
[4] ChemSusChem, 2011, vol. 4, # 1, p. 112 - 118.
[5] RSC Advances, 2016, vol. 6, # 93, p. 90232 - 90238.
[6] Patent: WO2010/102203, 2010, A2, . Location in patent: Page/Page column 26-27.
[7] Catalysis Letters, 2018, vol. 148, # 6, p. 1731 - 1738.
[8] Patent: US2763665, 1952, , .
[9] Catalysis Communications, 2019, p. 62 - 66.
  • 4
  • [ 71-23-8 ]
  • [ 6347-01-9 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791.
  • 5
  • [ 71-23-8 ]
  • [ 57-50-1 ]
  • [ 1917-66-4 ]
  • [ 645-67-0 ]
YieldReaction ConditionsOperation in experiment
65 %Spectr. at 180℃; for 40 h; 1.8 g of sucrose,0.361 g of SnCl4, 0. 058 g of BF3?, 20? Of n-propanol were added to 50 mLStainless steel-lined reactor with Teflon,Heated to 180 ° C,The reaction was carried out at that temperature for 40 h. Filtration,To remove unreacted sucrose and other insoluble impurities,The solvent was removed by rotary evaporation,2 mL H20 was added and the organic phase was extracted with methyl isobutyl ketone,The resulting organic phase was rotary evaporated to a high purity furan derivative,The isolated yield was 89percent. The qualitative analysis of the reaction products was carried out by gas chromatography-mass spectrometry (GC-MS)And with the standard material (HMF,Propoxyl methyl furfural and propyl propionate)The retention times in gas chromatography (GC) were compared and confirmed. Quantitative analysis of the yield distribution of different furan derivatives was determined by 4 NMR,The product distribution results are:5-propoxymethylfurfural was 65percent,HMF was 0percent and propyl levulinate was 35percent.
References: [1] Patent: CN103467418, 2016, B, . Location in patent: Paragraph 0021.
  • 6
  • [ 71-23-8 ]
  • [ 57-50-1 ]
  • [ 67-47-0 ]
  • [ 1917-66-4 ]
  • [ 645-67-0 ]
YieldReaction ConditionsOperation in experiment
72 %Spectr. at 100℃; for 10 h; 1.8 g of sucrose,0.271 g of GeCl4, 0.091 g of BBr3, and 20 mL of n-propanol were added to 50 mL of a polyTetrafluoroethylene-lined stainless steel reactor,Heated to l00 ° C,The reaction was carried out at that temperature for 10 h. Filtration,To remove unreacted sucrose and other insoluble impurities,The solvent was removed by rotary evaporation,2 mL H20 was added and the organic phase was extracted with methyl isobutyl ketone,The resulting organic phase was rotary evaporated to a high purity furan derivative,The isolated yield was 83percent. The qualitative analysis of the reaction products was carried out by gas chromatography-mass spectrometry (GC-MS)And with the standard material (HMF,5-propoxymethylfurfural and propyl propionate) in gas chromatography (GC) were compared and confirmed. Quantitative analysis of the yield distribution of different furan derivatives was confirmed by 1H NMR,The product distribution results are:5-propoxymethylfurfural was 72percent, HMF was 9percentPropyl propionate was 19percent
References: [1] Patent: CN103467418, 2016, B, . Location in patent: Paragraph 0020.
  • 7
  • [ 71-23-8 ]
  • [ 9004-34-6 ]
  • [ 645-67-0 ]
References: [1] ChemSusChem, 2016, vol. 9, # 23, p. 3307 - 3316.
  • 8
  • [ 71-23-8 ]
  • [ 470-23-5 ]
  • [ 645-67-0 ]
References: [1] RSC Advances, 2014, vol. 4, # 8, p. 4194 - 4202.
  • 9
  • [ 71-23-8 ]
  • [ 57-48-7 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2013, vol. 15, # 10, p. 2895 - 2903.
  • 10
  • [ 71-23-8 ]
  • [ 57-48-7 ]
  • [ 1917-66-4 ]
  • [ 111-43-3 ]
  • [ 110-74-7 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2013, vol. 15, # 10, p. 2895 - 2903.
  • 11
  • [ 71-23-8 ]
  • [ 6347-01-9 ]
  • [ 1917-66-4 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791.
  • 12
  • [ 6347-01-9 ]
  • [ 645-67-0 ]
References: [1] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791.
[2] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791.
  • 13
  • [ 98-00-0 ]
  • [ 71-23-8 ]
  • [ 65679-81-4 ]
  • [ 645-67-0 ]
References: [1] Catalysis Communications, 2015, vol. 59, p. 175 - 179.
  • 14
  • [ 71-23-8 ]
  • [ 37112-31-5 ]
  • [ 645-67-0 ]
References: [1] Chemistry of Natural Compounds, 1998, vol. 34, # 5, p. 582 - 589.
  • 15
  • [ 71-23-8 ]
  • [ 927-56-0 ]
  • [ 645-67-0 ]
References: [1] Patent: US2188340, 1936, , .
  • 16
  • [ 57-55-6 ]
  • [ 123-76-2 ]
  • [ 5413-49-0 ]
  • [ 645-67-0 ]
  • [ 1679-47-6 ]
References: [1] International Journal of Chemical Kinetics, 2019, .
 

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