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[ CAS No. 17739-45-6 ] {[proInfo.proName]}

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Chemical Structure| 17739-45-6
Chemical Structure| 17739-45-6
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Product Details of [ 17739-45-6 ]

CAS No. :17739-45-6 MDL No. :MFCD01321310
Formula : C7H13BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GCUOLJOTJRUDIZ-UHFFFAOYSA-N
M.W : 209.08 Pubchem ID :86621
Synonyms :

Calculated chemistry of [ 17739-45-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.69
TPSA : 18.46 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) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.22
Consensus Log Po/w : 1.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 2.05 mg/ml ; 0.00979 mol/l
Class : Soluble
Log S (Ali) : -1.7
Solubility : 4.14 mg/ml ; 0.0198 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.36 mg/ml ; 0.0065 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.45

Safety of [ 17739-45-6 ]

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 [ 17739-45-6 ]

* 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 [ 17739-45-6 ]
  • Downstream synthetic route of [ 17739-45-6 ]

[ 17739-45-6 ] Synthesis Path-Upstream   1~5

  • 1
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YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In dichloromethane; water at 0℃; for 5 h; To a solution of 2-bromoethanol 24 (50.0 g, 40 mmol) in methylene chloride (500 mL) cooled to 0 0C was added 3,4-dihydro-2H-pyran (40.32 g, 48 mmol) followed by p-TS A-H2O (100 mg) was added. Reaction mixture was stirred at 0 0C for 5.0 h. The reaction mixture was washed with aq NaHCO3 and brine, dried over Na2SO4 and evaporated to give the product 25 (75.0 g, 90percent). This crude product was taken to next step without purification.
89% With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2 h; To as solution of2-bromoethanol (3.8 g, 30.0 mmol) and DHP (2.5 g, 30.0 mmol) inDCM (50 mL), was added TsOH (380.0 mg, 2.2 mmol) in portions and the mixture was stirred atroom temperature for 2 hrs. The reaction was concentrated and purified by silica gel column(PE/EA '" 50/l) to g1ve 2-(2-bromoethoxy)tetrahydro-2H-pyran (5.6 g, yield: 89 percent) as acolorless oil.
78% With toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; Step 5 2-(2-Bromoethoxy)tetrahydro-2H-pyran:; 3,4-Dihydro-2H-pyran (7.80 g, 92.72 mmol) was added dropwise to a mixture of 2-bromoethanol (10.00 g, 80.03 mmol), p-toluenesulfonic acid monohydrate (1.52 g, 7.99 mmol) and dry dichloromethane (50 mL) at about 0° C. The reaction mixture was stirred at ambient temperature for about 24 hours. The volatiles were removed in vacuo to provide a crude residue. The residue was purified by silica gel column chromatography (diethyl ether) to afford the title product as a dark oil which was used in the next step without further purification (13.00 g, 78percent). 1H NMR (400 MHz, CDCl3) δ 1.48-1.91 (m, 6H), 3.44-3.55 (m, 3H), 3.72-3.81 (m, 1H), 3.83-3.93 (m, 1H), 3.96-4.04 (m, 1H), 4.67 (t, J=3.6 Hz, 1H); IR (film) ν 2943, 2885, 1448, 1353, 1274 cm-1.
72% With pyridinium p-toluenesulfonate In dichloromethane at 0 - 20℃; for 4 h; Intermediate 2 2-(2-bromoethoxy)tetrahydro-2H-pyran To a solution of 2-bromoethanol (15 g, 0.12 mol) in DCM (150 mL) was added PPTS (891 mg, 3.6 mmol), then dihydropyran (10.6 g, 0.126 mol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 4 h. It was partitioned between DCM and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (50: 1) to give 2-(2-bromoethoxy)tetrahydro-2H-pyran(18.0 g, 72.0percent yield) as a light yellow oil.
69% With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 8 h; 2-Bromoethanol (2 g, 16.0 mmol, 1 eq), 3,4-dihydropyran (2.15 g, 25.6 mmol, 1.6 eq) was dissolved in 40 mL of dichloromethane and PPTS (0.402 g , 1.6 mmol, 0.1 eq) was added and the reaction was stirred at room temperature for 8 hours,The reaction was carried out. After completion of the reaction, the reaction was complete and the reaction was complete. The organic phase was separated by the addition of 10 mL of water. The organic phase was dried over anhydrous sodium sulfate and dried. Column chromatography PE: EA (v / v) = 20: 1 gave 2.3 g of product , The yield was 69percent.
60% With toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; for 5 h; To a solution of 2-bromo ethanol 13-1 (5 g, 40 mmol) in DCM (250 mL) was added /?-toluenesulfonic acid (760 mg, 4 mmol) followed by dihydropyran (4.3 mL, 48 mmol) at 0 °C and stirred at RT for 5 hr. The reaction mixture was diluted with EtOAc (100 mL) washed with water (100 mL), brine (10 mL) and dried over Na2S04, and concentrated under reduced pressure at 25 °C. The crude compound was purified using silica gel chromatography (5percent EtOAc in hexanes) to afford 13-2 (5 g, 24 mmol, 60percent yield) as a pale yellow color liquid.

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  • 2
  • [ 142-68-7 ]
  • [ 540-51-2 ]
  • [ 17739-45-6 ]
YieldReaction ConditionsOperation in experiment
80% at 20℃; Step 1 (Synthesis of Compound 1-2) (0075) Compound 1-1 (12.5 g, 100 mmol) was dissolved in methanol (30 mL), and THP (12.6 g, 150 mmol), p-TsOH (250 mg, 1.3 mmol) were added at room temperature, stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and then purified by silica gel column chromatography with an eluent system (PE: EtOAc=30:1) to obtain the product 1-2, yield: 80percent. (0076) 1H NMR (400 MHz, CDCl3) δ: 4.68 (t, J=3.6 Hz, 1H), 4.03 (td, J=6.4, 11.2 Hz, 1H), 3.90 (ddd, J=3.0, 8.4, 11.2 Hz, 1H), 3.73-3.82 (m, 1H), 3.45-3.58 (m, 3H), 1.80-1.91 (m, 1H), 1.70-1.79 (m, 1H), 1.51-1.63 (m, 4H).
Reference: [1] Patent: US2017/197986, 2017, A1, . Location in patent: Paragraph 0074; 0075; 076
  • 3
  • [ 110-87-2 ]
  • [ 144-55-8 ]
  • [ 540-51-2 ]
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Reference: [1] Patent: US4851387, 1989, A,
  • 4
  • [ 142-68-7 ]
  • [ 627-18-9 ]
  • [ 17739-45-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7693 - 7704
  • 5
  • [ 17739-45-6 ]
  • [ 40365-61-5 ]
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 2001, vol. 171-172, p. 167 - 172
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