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[ CAS No. 26272-83-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 26272-83-3
Chemical Structure| 26272-83-3
Chemical Structure| 26272-83-3
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Product Details of [ 26272-83-3 ]

CAS No. :26272-83-3 MDL No. :MFCD08544401
Formula : C10H12O4S Boiling Point : -
Linear Structure Formula :- InChI Key :UMFWNFVHKAJOSE-UHFFFAOYSA-N
M.W : 228.26 Pubchem ID :13153907
Synonyms :

Calculated chemistry of [ 26272-83-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.17
TPSA : 60.98 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) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.63 mg/ml ; 0.00713 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.66 mg/ml ; 0.00726 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.8
Solubility : 0.363 mg/ml ; 0.00159 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.55

Safety of [ 26272-83-3 ]

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 [ 26272-83-3 ]

* 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.

  • Upstream synthesis route of [ 26272-83-3 ]
  • Downstream synthetic route of [ 26272-83-3 ]

[ 26272-83-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 26272-83-3 ]
  • [ 26272-85-5 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 15, p. 3259 - 3262
  • 2
  • [ 7748-36-9 ]
  • [ 98-59-9 ]
  • [ 26272-83-3 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In water at 20℃; for 18 h; Scheme 613 Step 1 14 Step 2 15Step 1To a solution of 1.00 g (13.5 mmol) of compound 13 and 7.6 mL (54.0 mmol) of triethylamine in 27 mL of methylene chloride was added 5.15 g (27.0 mmol) of p- toluenesulfonyl chloride. The reaction mixture was stirred at room temperature overnight. After this time, the reaction was quenched with saturated 150 mL of aqueous sodium bicarbonate and extracted with three 50 mL portions of methylene chloride. The combined extracts were concentrated and the resulting residue was purified by column chromatography (silica, 0-25percent EtOAc/hexanes) to give 1.22 g (94percent) of 14 as white solid: NMR (CDCI3 500 MHz) δ 7.78 (d, J= 8.5 Hz, 2H), 7.36 (d, J= 9.0 Hz, 2H), 5.29 (m, 1H), 4.69 (m, 4H), 2.46 (s, 3H).
85% With sodium hydroxide In water at 0℃; for 3 h; At 0° C., aqueous NaOH solution (2 N, 15 mL) was added dropwise to a solution of oxetan-3-ol (1.48 g, 20 mmol) and p-toluene sulfonyl chloride (4.18 g, 22 mmol) in water (50 mL). After stirred for 3 hours, the mixture was treated with water (100 mL), extracted with dichloromethane (100 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, then filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=10:1) to give compound 39-c (3.9 g, yield: 85percent). LC-MS (ESI): m/z=229 [M+H]+.
78% at 20℃; Inert atmosphere ;To a 50 mL two-neck flask were added oxetan-3-ol (1.00 g, 13.0 mmol) and anhydrous pyridine (25 mL), then paratoluensulfonyl chloride (3.10 g, 16.0 mmol) was added to the mixture under nitrogen protection.
The reaction mixture was stirred at rt overnight.
The reaction was mornitored by TLC until oxetan-3-ol consumed completely, then the mixture was concentrated in vacuo to remove pyridine.
To the residue was added saturated brine (60 mL).
The resulting mixture was extracted with EtOAc (20 mL*3).
The combined organic layers were washed with saturated brine (30 mL*2), dried over anhydrous Na2SO4, and filtered.
The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (PE:EtOAc=10:1, V/V) to give a white solid (2.40 g, 78.0percent).
MS(ESI, pos.ion)m/z:229.1 (M+1);
65% With sodium hydroxide In water at 50℃; for 1 h; To a well-stirred 50° C. solution of Part D compound (7 g, 94 mmol) and p-TsCl (12.8 g, 67.1 mmol) in water (15 mL) was added dropwise a solution of NaOH (2.69 g, 67.1 mmol) in water (15 mL). The reaction was heated for 1 h at 50° C., then cooled to RT and toluene (10 mL) was added. The aqueous layer was extracted with toluene (5 mL.x.2). The combined organic extracts were washed with conc NH4OH (3.x.) and water (2.x.), then concentrated in vacuo. Hexane (50 mL) was added to the residue and a solid was formed, which was collected by filtration and then was dried in vacuo for 1 h to give Part E compound (10 g, 65percent yield) as a white solid. [M+H]+=229.1; 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (s, 3 H), 4.64-4.75 (m, 4 H), 5.27-5.34 (m, 1 H), 7.37 (d, J=8.25 Hz, 2 H), 7.78 (d, J=8.25 Hz, 2 H).
62% at 20℃; for 18 h; Preparation of toluene-4-sulfonic acid oxetan-3-yl ester; To a solution of oxetan-3-ol (1.0 g, 13.0 mmol) in anhydrous pyridine (25 ml_) at room temperature was added 4-toluene sulfonyl chloride (3.09 g, 16.2 mmol). After stirring the reaction mixture for 18 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30percent ethyl acetate in heptane to afford 1.9 g (62percent yield) of the desired product as a white solid.1H NMR (400 MHz, chloroform-d) delta ppm 2.46 (s, 3 H), 4.63 - 4.75 (m, 4 H), 5.26 - 5.34 (m, 1 H), 7.36 (d, J=8.00 Hz, 2 H), 7.78 (d, J=8.40 Hz, 2 H).
50% With triethylamine In dichloromethane at 20℃; for 15 h; Step 1: To a stirred mixture of oxetan-3-ol (0.85 g, 11.5 mmol) in DCM (38 mL) were added TEA (3.3 mL, 23mmol) and 4-methylbenzene-1-sulfonyl chloride (2.7 g, 13.8 mmol). The reaction mixture was stirred at rt for 15 h. Themixture was partitioned between water and DCM. The organic layer was separated, dried over Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradientof 30percent DCM in petroleum ether to 100percent DCM to afford oxetan-3-yl 4-methylbenzenesulfonate (1.3 g, 50percent) as a whitesolid. 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J = 8.4 Hz, 2H), 7.35 (d, J = 8.7 Hz, 2H), 5.30 (m, 1H), 4.66 - 4.74 (m, 4H),2.46 (s, 3H); LCMS (ESI) m/z 229 (M+H)+

Reference: [1] Patent: WO2012/138678, 2012, A1, . Location in patent: Page/Page column 33
[2] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2953 - 2956
[3] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0290; 0291
[4] Patent: EP3342765, 2018, A1, . Location in patent: Paragraph 0293
[5] Patent: US2008/9465, 2008, A1, . Location in patent: Page/Page column 82
[6] Organic Letters, 2008, vol. 10, # 15, p. 3259 - 3262
[7] Patent: WO2010/23594, 2010, A1, . Location in patent: Page/Page column 34
[8] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 0974
[9] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 2, p. 433 - 442
[10] Patent: US2007/66620, 2007, A1, . Location in patent: Page/Page column 14
  • 3
  • [ 269410-08-4 ]
  • [ 26272-83-3 ]
  • [ 1339890-99-1 ]
Reference: [1] Patent: WO2014/37751, 2014, A1, . Location in patent: Paragraph 00419
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