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[ CAS No. 345216-96-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 345216-96-8
Chemical Structure| 345216-96-8
Chemical Structure| 345216-96-8
Structure of 345216-96-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 345216-96-8 ]

CAS No. :345216-96-8 MDL No. :MFCD13619933
Formula : C9H14O4 Boiling Point : -
Linear Structure Formula :- InChI Key :IMGDPCBVSHGKDZ-UHFFFAOYSA-N
M.W :186.21 Pubchem ID :9964279
Synonyms :

Calculated chemistry of [ 345216-96-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.57
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 0.17
Log Po/w (WLOGP) : 0.55
Log Po/w (MLOGP) : 0.05
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.9
Solubility : 23.2 mg/ml ; 0.125 mol/l
Class : Very soluble
Log S (Ali) : -0.83
Solubility : 27.4 mg/ml ; 0.147 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.41
Solubility : 7.23 mg/ml ; 0.0388 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 345216-96-8 ]

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

Application In Synthesis of [ 345216-96-8 ]

* 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 [ 345216-96-8 ]
  • Downstream synthetic route of [ 345216-96-8 ]

[ 345216-96-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 345216-96-8 ]
  • [ 137052-08-5 ]
YieldReaction ConditionsOperation in experiment
96% at 120℃; for 1.5 h; Example 1
(Synthesis of 4-acetyltetrahydropyran)
In a flask made of glass having an inner volume of 10 ml and equipped with a stirring device, a thermometer and a reflux condenser were charged 0.38 g (2.0 mmol) of 4-acetyl-4-methoxycarbonyltetrahydropyran with a purity of 99percent and synthesised in the same manner as in Reference example 1 and 1.08 ml (10 mmol) of 9 mol/l sulfuric acid, and the mixture was reacted at 120°C for 1.5 hours with stirring.
After completion of the reaction, when the reaction mixture was analyzed by gas chromatography (Internal standard method), 0.25 g (Reaction yield: 96percent) of 4-acetyltetrahydropyran was found to be formed.
90% at 120℃; for 4 h; Example 2
(Synthesis of 4-acetyltetrahydropyran)
In a flask made of glass having an inner volume of and equipped with a stirring device, a thermometer and a reflux condenser were charged 0.38 g (2.0 mmol) of 4-acetyl-4-methoxycarbonyltetrahydropyran with a purity of 99percent and synthesised in the same manner as in Reference example 1 and 2.52 ml (10 mmol) of 4 mol/l hydrochloric acid, and the mixture was reacted at 120°C for 4 hours with stirring.
After completion of the reaction, when the reaction mixture was analyzed by gas chromatography (Internal standard method), 0.23 g (Reaction yield: 90percent) of 4-acetyltetrahydropyran was found to be formed.
85% With sodium hydroxide; water; dihydrogen peroxide In methanol at 40℃; for 5 h; In a flask made of glass having an inner volume of 10 ml and equipped with a stirring device, a thermometer, a dropping funnel and a reflux condenser were charged 202 g (1.0 mol) of 4-acetyl-4-methoxycarbonyltetrahydropyran with a purity of 95percent and synthesized in the same manner as in Reference example 1 and 720 ml of methanol, and the temperature of the mixture was raised to 35°C with stirring. Then, to the mixture was gently added dropwise a mixed solution comprising 201 g (2.0 mol) of 35percent by weight aqueous hydrogen peroxide solution and 91 ml (0.73 mol) of 8 mol/l aqueous sodium hydroxide solution, and the mixture was reacted at 40°C for 5 hours with stirring. After completion of the reaction, to the resulting reaction mixture was added a saturated aqueous sodium sulfate solution to decompose the remaining hydrogen peroxide, then, the mixture was concentrated under reduced pressure, and the concentrate was extracted three times with 500 ml of ethyl acetate. The organic layer was distilled under reduced pressure (90 to 92°C, 2.0 kPa) to give 113 g (Isolation yield: 85percent) of 4-acetyltetrahydropyran with a purity of 99percent (areal percentage by gas chromatography) as a colorless liquid. Physical properties of the 4-acetyltetrahydropyran are as follows. CI-MS (m/e); 129 (M+1) 1H-NMR (CDCl3, δ (ppm)); 1.60 to 1.82 (4H, m), 2.16 (3H, s), 2.50 to 2.61 (1H, m), 3.39 to 3.47 (2H, m), 3.96 to 4.02 (2H, m)
65% at 120℃; for 1 h; Example 3
(Synthesis of 4-acetyltetrahydropyran)
In a flask made of glass having an inner volume of 10 ml and equipped with a stirring device, a thermometer and a reflux condenser were charged 0.38 g (2.0 mmol) of 4-acetyl-4-methoxycarbonyltetrahydropyran with a purity of 99percent and synthesised in the same manner as in Reference example 1 and 1.70 g (10 mmol) of 47percent hydrobromic acid, and the mixture was reacted at 120°C for 1 hour with stirring.
After completion of the reaction, when the reaction mixture was analyzed by gas chromatography (Internal standard method), 0.17 g (Reaction yield: 65percent) of 4-acetyltetrahydropyran was found to be formed.
10.874 g With sulfuric acid In water; isopropyl alcohol for 48 h; Reflux The mixture of methyl acetylacetate (24.770 g, 211.18 mmol), bis(2-chloroethyl) ether (30.506 g, 211.18 mmol), potassium carbonate (64.861 g, 464.59 mmol) and sodium iodide (31.974 g, 211.18 mmol) in N,N-dimethylformamide (1065 ml) was heated at 80°C for 18 hours. The mixture was cooled to room temperature, further portions of potassium carbonate (29.430 g, 210.80 mmol) and sodium iodide (31.974 g, 211.18 mmol) were added and the whole was heated at 80°C for further 2 hours. The reaction mixture was filtered over celite, washed with ethyl acetate (500 ml), then organic layer was washed with water (300 ml), brine (150 ml) and dried over sodium sulphate. Drying agent and solvent were removed to obtain 26.600 g of the intermediate compound methyl 4-acetyl- tetrahydro-2H-pyran-4-carboxylate. To the obtained compound (26.600 g, 112.47 mmol) isopropanol (125 ml), water (125 ml) and concentrated sulphuric acid (55.151 g, 562.37 mmol) were added and the whole was heated at reflux for 48 hours. The mixture was alkalized with sodium hydroxide solution (45.5 g NaOH in 500 ml of water). Aqueous layer was extracted with chloroform (3 x 100 ml). Extracts were dried over sodium sulphate. Crude product obtained after removing drying agent and solvent in the form of a brown liquid was distilled under reduced pressure using Vigreux column and collecting fraction boiling at 75-83°C/20 mm Hg. 10.874 g of the title product were obtained (yield 36.4percent) in the form of a colorless liquid.1H NMR (300 MHz, CDCl3): δ 4.03-3.97 (m, 2H), 3.47-3.38 (m, 2H), 2.54 (m, 1 H), 2.16 (s, 3H), 1.78-1.69 (m, 4H). 13C NMR (75 MHz, CDCl3): δ 209.86, 67.13, 48.03, 28.00, 27.48.

Reference: [1] Patent: EP1700852, 2006, A1, . Location in patent: Page/Page column 7-8
[2] Patent: EP1700852, 2006, A1, . Location in patent: Page/Page column 8
[3] Patent: EP1700852, 2006, A1, . Location in patent: Page/Page column 8
[4] Patent: EP1700852, 2006, A1, . Location in patent: Page/Page column 8
[5] Patent: WO2011/50016, 2011, A1, . Location in patent: Page/Page column 35-36
[6] Patent: WO2014/24125, 2014, A1, . Location in patent: Page/Page column 26
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