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Chemical Structure| 10374-51-3 Chemical Structure| 10374-51-3

Structure of 10374-51-3

Chemical Structure| 10374-51-3

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Product Details of [ 10374-51-3 ]

CAS No. :10374-51-3
Formula : C5H8O3
M.W : 116.12
SMILES Code : O=C1OC(CO)CC1
MDL No. :MFCD00506240
InChI Key :NSISJFFVIMQBRN-UHFFFAOYSA-N
Pubchem ID :98431

Safety of [ 10374-51-3 ]

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

Computational Chemistry of [ 10374-51-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 26.48
TPSA ?

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

46.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.93
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

-0.44
Log Po/w (WLOGP)?

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

-0.32
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

0.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.1

Water Solubility

Log S (ESOL):?

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

-0.22
Solubility 70.5 mg/ml ; 0.607 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.

-0.07
Solubility 98.4 mg/ml ; 0.848 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

-0.16
Solubility 79.8 mg/ml ; 0.687 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

No
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.

-7.32 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)

2.03

Application In Synthesis of [ 10374-51-3 ]

* 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 [ 10374-51-3 ]

[ 10374-51-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 591-80-0 ]
  • [ 10374-51-3 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride; dihydrogen peroxide; In methanol; formic acid; EXAMPLE 56 (+-)-Dihydro-5-Hydroxymethyl-2(3H) -Furanone STR89 To a stirring solution of 19% hydrogen peroxide (35 mL, 0.20 mol) in 85% aqueous formic acid (60 mL) at 50-55 C. was added over a 15 min period a solution of 4-pentenoic acid (15 g, 0.15 mol) in 85% aqueous formic acid (30 mL). The solution was maintained at this temperature for 2 h. Concentration gave an oil which comprised of a mixture of the desired compound and the corresponding formate ester. The oil was then stirred in methanol (50 mL) containing concentrated hydrochloric acid (1 mL) for 3 h. Concentration gave the desired compound as an oil (17.2 g, 99%). 1 H NMR (300 MHz, CDCl3) delta: 4.60 (m, 1H, H-5), 3.89 (dd, 1H, H-6, J=2.7 HZ and 12.6 Hz), 3.63 (dd, 1H, H-6', J=4.5 HZ and 12.3 Hz), 2.6 (m, 2H, H-3), 2.3 (m, 3H, H-4, OH).
97% With formic acid; dihydrogen peroxide; at 50℃; for 2.25h; 4-pentenoic acid (2 g, 20 mmol) was dissolved in formic acid (5 mL), and added dropwise into formic acidsolution (20 mL) containing 35% of hydrogen peroxide (28 mmol) at 50 C over 15 min. At this temperature, the mixturewas stirred for 2 h, and distilled under reduced pressure to give the product 2-keto-5-hydroxymethyl-tetrahydrofuran (2g, yield 97%).
88% With dihydrogen peroxide; In tert-butyl alcohol; EXAMPLE 5 A total of 2 ml of 30% by weight hydrogen peroxide aqueous solution was added dropwise to a stirred mixture of 1.00 g (10 mmol) of 4-pentenoic acid, 25 mg (0.1 mmol) of tungstic acid, and 15 ml of t-butyl alcohol at room temperature, followed by stirring at 70C for 10 hours. As a result, gamma-hydroxymethyl-gamma-butyrolactone was produced in a yield of 88%.
With N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamineiron(II) bis(triflate); dihydrogen peroxide; In water; acetonitrile; for 0.166667h;Inert atmosphere; Schlenk technique; General procedure: Epoxidations were performed in 25-mL Schlenk tubes under an inert atmosphere. In a typical run, the tube was charged with 1 equiv of catalyst (typically about 15mg), degassed acetonitrile (20mL) and 200 equiv of substrate. 600 equiv of the oxidant H2O2 (30% w/v in water) were added via syringe over a two-minute period, often resulting in an immediate color change to brown. This color faded to a pale orange for most substrates over a period of 30s. The reaction was allowed to stir for a total of 10min, and then was quenched by pouring the solution into an Erlenmeyer flask containing silica gel and anhydrous magnesium sulfate. The solution was passed through a short column of silica gel, and solvent evaporated under moderate vacuum. As a control, samples of substrates were taken through this workflow without use of catalyst, and analyzed gravimetrically and by 1H NMR. Pure substrate was recovered with no significant mass loss (typical recovery 98%). For other catalyst:substrate:oxidant ratios, the concentration of catalyst was kept constant, and amounts of substrate and oxidant varied. The products were analyzed by 1H NMR in CDCl3 with a relaxation delay of 10s. 1H NMR shifts of the epoxide products matched those reported in the literature [22,36-39]. For oleic acid and ethyl oleate, the shift of the CH3 group of C18 does not change between the starting materials and products. This signal was therefore used as an internal standard to measure conversions by comparing the integrations of the alkene signals relative to the methyl signals [36]. Similarly, epoxide selectivities were calculated from the integrations of the epoxide signals and the methyl signals. For undecylenic acid and methyl undecenoate, a similar approach utilized the methylene group next to the carboxylic acid group as an internal standard. For the epoxidation of 4-pentenoic acid and 5-hexenoic acid, conversions were determined by comparing the integrations of the alkene signals with those of the epoxide and lactone signals. GC-MS data was used to confirm the presence of two major products only, the epoxide and the lactone [38]. Owing to the limit of sensitivity of NMR, in experiments where epoxide or lactone was the only product clearly detected, selectivities of >95% are reported, as low concentrations of other products can not be ruled out. Selected spectra and GC-MS chromatograms are available in the Supplemental information.

  • 2
  • [ 66679-29-6 ]
  • [ 10374-51-3 ]
  • 3
  • [ 10374-51-3 ]
  • [ 38806-07-4 ]
  • 4
  • [ 10374-51-3 ]
  • [ 108-24-7 ]
  • [ 5904-80-3 ]
  • 5
  • [ 10374-51-3 ]
  • [ 39928-72-8 ]
  • 6
  • [ 10374-51-3 ]
  • [ 32730-32-8 ]
  • 7
  • [ 10374-51-3 ]
  • [ 1729-32-4 ]
  • 8
  • [ 10374-51-3 ]
  • sodium 2,3-dideoxy-D,L-glycero-pentonate [ No CAS ]
  • 10
  • [ 86310-98-7 ]
  • [ 10374-51-3 ]
  • 11
  • [ 73927-91-0 ]
  • [ 107-18-6 ]
  • [ 10374-51-3 ]
  • 12
  • [ 10374-51-3 ]
  • [ 74-88-4 ]
  • [ 96845-45-3 ]
  • 13
  • [ 10374-51-3 ]
  • [ 18162-48-6 ]
  • [ 193095-16-8 ]
  • 14
  • [ 27620-83-3 ]
  • [ 10374-51-3 ]
  • 15
  • [ 23107-52-0 ]
  • [ 10374-51-3 ]
  • 16
  • [ 144-48-9 ]
  • [ 107-18-6 ]
  • [ 10374-51-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 7 6.0 g 4,5-epoxypentane carboxylic acid methyl ester is shaken in a mixture of 10 ml ether and 10 ml 2 n HCl for 1 hour. The ether is then separated and the aqueous phase perforated with ether. From the combined dried ethereal phases 3.7 g dihydro-5-hydroxymethyl-(3H)-furanone is obtained after removal of the ether in vacuum.
EXAMPLE 10 6.0 g 4,5-epoxypentane carboxylic acid methyl ester is shaken in a mixture of 10 ml ether and 10 ml 2n HCl for 1 hour. The ether is then separated and the aqueous phase perforated with ether. From the combined dried ethereal phases 3.7 g dihydro-5-hydroxymethyl-(3H)-furanone is obtained after removal of the ether in vacuum.
  • 18
  • δ-bromo-γ-valerolactone [ No CAS ]
  • [ 10374-51-3 ]
  • 19
  • δ-chloro-γ-valerolactone [ No CAS ]
  • [ 10374-51-3 ]
  • 20
  • (+-)-4,5-dibromo-valeronitrile [ No CAS ]
  • [ 10374-51-3 ]
  • 21
  • (+-)-5-bromo-4-hydroxy-valeric acid-lactone [ No CAS ]
  • [ 10374-51-3 ]
  • 22
  • [ 591-80-0 ]
  • Merrifield resin [ No CAS ]
  • [ 10374-51-3 ]
  • 23
  • [ 64-69-7 ]
  • [ 107-18-6 ]
  • [ 10374-51-3 ]
  • 25
  • [ 58839-90-0 ]
  • [ 10374-51-3 ]
  • 26
  • [ 10374-51-3 ]
  • [ 136892-36-9 ]
  • 27
  • [ 10374-51-3 ]
  • tert-Butyl-(5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane [ No CAS ]
  • 28
  • [ 71834-72-5 ]
  • [ 10374-51-3 ]
  • 29
  • 5-Diethoxymethyl-dihydro-furan-2-one [ No CAS ]
  • [ 10374-51-3 ]
  • 30
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 78508-97-1 ]
  • 31
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 96845-44-2 ]
  • 32
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 96845-44-2 ]
  • 33
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 96845-46-4 ]
  • 34
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 96845-47-5 ]
  • 35
  • [ 10374-51-3 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 96845-51-1 ]
 

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Technical Information

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