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[ CAS No. 25637-18-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 25637-18-7
Chemical Structure| 25637-18-7
Chemical Structure| 25637-18-7
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Product Details of [ 25637-18-7 ]

CAS No. :25637-18-7 MDL No. :MFCD06797467
Formula : C5H9IO Boiling Point : -
Linear Structure Formula :- InChI Key :JTRNQTFTRDPITG-UHFFFAOYSA-N
M.W : 212.03 Pubchem ID :2795506
Synonyms :

Calculated chemistry of [ 25637-18-7 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.08
TPSA : 9.23 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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 1.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.52 mg/ml ; 0.00718 mol/l
Class : Soluble
Log S (Ali) : -1.37
Solubility : 8.96 mg/ml ; 0.0422 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.74
Solubility : 3.9 mg/ml ; 0.0184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 25637-18-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25637-18-7 ]

* 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 [ 25637-18-7 ]
  • Downstream synthetic route of [ 25637-18-7 ]

[ 25637-18-7 ] Synthesis Path-Upstream   1~3

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  • [ 2081-44-9 ]
  • [ 25637-18-7 ]
YieldReaction ConditionsOperation in experiment
64.3% With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; A RBF was charged with tetrahydro-2H-pyran-4-ol (2.0 g, 19.58 mmol), imidazole (1.600 g, 23.50 mmol), triphenylphosphine (5.39 g, 20.56 mmol), and tetrahydrofuran (39.2 ml) and cooled to 0° C. A solution of iodine (5.96 g, 23.50 mmol) in tetrahydrofuran (39.2 ml) was added slowly dropwise.
The reaction was warmed to room temperature and stirred overnight.
The reaction was diluted with ethyl acetate and washed with water.
The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated.
The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-50percent EtOAc:Heptane) to afford 4-iodotetrahydro-2H-pyran (2.67 g, 12.59 mmol, 64.3percent yield) as a clear light yellow oil.
51% With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 15℃; for 16 h; Inert atmosphere To a solution of tetrahydropyran-4-ol (15.0 g, 146 mmol, 14.71 mL) in dichloromethane (600 mL) was added PPh3 (50.0 g, 191 mmol) and imidazole (15.0 g, 220 mmol). The mixture was stirred at 0 °C and iodine (44.7 g, 176 mmol) was added in portions under a nitrogen atmosphere. Finally, the mixture was stirred at 15 °C for 16 hours. On completion, the reaction mixture was filtered and the filtrate was concentrated in vacuo to get a residue. The residue was diluted with water (150 mL) and extracted with ethyl acetate (3 × 150 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether: dichloromethane = 1:0 to 2:1) to give the title compound (16.0 g, 51percent yield) as a colorless oil.1H NMR (400MHz, CDCl3) δ = 4.48 - 4.41 (m, 1H), 3.80 (td, J = 4.4, 11.6 Hz, 2H), 3.56 - 3.46 (m, 2H), 2.20 - 2.09 (m, 4H).
9.6 g With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2 h; Inert atmosphere Synthesis of compound 97.2. [00609] A solution of oxan-4-ol, compound 97.1 (7.0 g, 68.54 mmol, 1.00 equiv) in dichloromethane (100 mL) was added triphenylphosphine (27.0 g, 102.94 mmol, 1.50 equiv) and imidazole (7.0 g, 102.82 mmol, 1.50 equiv) at room temperature. This was followed by addition of iodine (18.3 g, 72.05 mmol, 1.05 equiv) in several batches at 0°C. The resulting solution was stirred for 2 h at room temperature under nitrogen. After completion, the reaction was quenched with 5percent HC1 solution, extracted with dichloromethane (100 mL x 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Crude was purified via flash column chromatography to afford 9.6 g of 4-iodooxane, compound 97.2 as colorless oil.
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8110 - 8113
[2] Patent: US9212182, 2015, B2, . Location in patent: Page/Page column 79
[3] Organic Letters, 2013, vol. 15, # 7, p. 1658 - 1661
[4] Patent: WO2018/106636, 2018, A1, . Location in patent: Paragraph 00281
[5] Journal of the Chemical Society, 1952, p. 910,913
[6] Angewandte Chemie - International Edition, 2008, vol. 47, # 48, p. 9334 - 9336
[7] Patent: WO2014/194242, 2014, A2, . Location in patent: Paragraph 00608-00609
[8] Organic Letters, 2017, vol. 19, # 23, p. 6412 - 6415
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Reference: [1] Journal of the Chemical Society, 1952, p. 910,913
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  • [ 108-97-4 ]
  • [ 25637-18-7 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 910,913
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