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[ CAS No. 13669-05-1 ]

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Chemical Structure| 13669-05-1
Chemical Structure| 13669-05-1
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Product Details of [ 13669-05-1 ]

CAS No. :13669-05-1 MDL No. :MFCD00208362
Formula : C12H10O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :QJGKCQWQNOPAMG-UHFFFAOYSA-N
M.W :250.34 Pubchem ID :151814
Synonyms :

Calculated chemistry of [ 13669-05-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.17
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.91
TPSA : 90.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.88
Log Po/w (WLOGP) : 3.66
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 5.27
Consensus Log Po/w : 3.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.115 mg/ml ; 0.000458 mol/l
Class : Soluble
Log S (Ali) : -4.44
Solubility : 0.00903 mg/ml ; 0.0000361 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0171 mg/ml ; 0.0000684 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.23

Safety of [ 13669-05-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13669-05-1 ]

* 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 [ 13669-05-1 ]
  • Downstream synthetic route of [ 13669-05-1 ]

[ 13669-05-1 ] Synthesis Path-Upstream   1~24

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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
  • 2
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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
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YieldReaction ConditionsOperation in experiment
76% With aluminum (III) chloride In dichloromethane at 40℃; for 4 h; A solution of thiophene (9.6 mL, 0.12 mol) and succinychloride (5.4 mL,0.05 mol) were added dropwise to a suspension containing AlCl3 (16.2 g, 0.12 mol) in 100 mL of dichloromethane. After stirringfor 4 h at 40 °C, the mixture solution was poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 30 min. The resulting solution was extracted with CHCl2 and washed with NaHCO3 solutions and water before desiccation with anhydrous MgSO4. The solvent was evaporated off, and the solid residues were purified by column chromatography to afford white product with ayield of 76percent. 1H NMR (500 MHz, CDCl3, 25 °C, TMS, d): 7.84 (dd,J = 3.8,1.1 Hz, 2H), 7.67 (dd, J = 5.0, 1.1 Hz, 2H), 7.17 (dd, J = 4.9, 3.8 Hz,2H), 3.42 (s, 4H). MALDI-TOF MS (mass m/z): 251.1 [M+ + H].
68% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4 h; A solution of thiophene (9.61 mL, 0.12 mol) and AlCl3 (16 g, 0.12 mol) in dry CH2Cl2 (50 mL) was added dropwise to a suspension of succinyl chloride (5.5 mL, 0.05 mol) in dry CH2Cl2 (50 mL) at 0 °C. The mixture was stirred for at 18-20 °C 4 h and poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 1 h and the resulting dark green organic phase was washed with concentrated NaHCO3 (3 x 25 mL), and dried over Na2SO4. After the solvent was evaporated, a blue-green solid remained and was suspended in ethanol. Column chromatography (SiO2, CH2Cl2) and recrystallization from ethanol produced 8.98 g (68percent) of it in a white solid. 1H NMR: (400 MHz; CDCl3): 7.80 (dd, 2H), 7.63 (dd, 2H), 7.13 (dd, 2H), 3.38 (s, 4H).
58% With aluminum (III) chloride In dichloromethane at 20℃; for 6 h; To a suspension of AlCl3 (32 g, 0.24 mol) in 90 mL ofDCM, a solution of 11 mL (0.1 mol) succinyl chloride and19.2 mL (0.24 mol) of thiophene in 30 mL DCM was addeddropwise at room temperature. The suspension was stirredfor 6 h and poured into a mixture of 10 mL of hydrochloricacid and 400 g of ice. The color of the suspension turnedfrom red to dark green after further stirring for 30 min.The organic phase was collected and the aqueous phasewas extracted with DCM. The organic phases was combinedand washed with water and saturated aqueous NaHCO3,dried over NaSO4, concentrated in vacuo, and purified bycolumn chromatography (eluent:DCM:hexane = 1:1) toafford 14.5 g (58percent) of 1 as pale blue crystals. 1H NMR(500 MHz, CDCl3, d, ppm): 7.82 (dd, 2H), 7.65 (dd, 2H),7.15 (dd, 2H), 3.40 (s, 4H) (Fig. S1). MS (EI) (m/z): [M]+ calcdfor C12H10O2S2, 250.0; found, 250.1.
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  • 4
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YieldReaction ConditionsOperation in experiment
51% With titanium(IV) isopropylate; ethylmagnesium bromide In tetrahydrofuran; diethyl ether; water at 23℃; for 18 h; Inert atmosphere General procedure: Ti(OiPr)4 (0.18 mL, 0.602 mmol) was added to a solution of 2-bromoacetophenone (4, 100. mg, 0.502 mmol) in THF (5 mL) atroom temperature. EtMgBr (0.47 mL, 1.41 mmol, 3 M in Et2O)was then added dropwise over 20 min during which the reactionmixture turned from clear to yellow to black. After 18 h,water (5 mL) was added, and the mixture was extracted EtOAc(3 × 5 mL). The combined organic layers were washed withbrine (1 × 10 mL), dried with MgSO4, and concentrated in vacuo.Purification by column chromatography (15percent EtOAc/hexanes)afforded 1,4-diketone 8 as a white powder (47 mg, 79percent).
Reference: [1] Synlett, 2018, vol. 29, # 16, p. 2195 - 2198
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  • 6
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[2] Reactive and Functional Polymers, 2012, vol. 72, # 8, p. 533 - 541
  • 7
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  • 8
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 11, p. 3045 - 3049
  • 9
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Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 8, p. 873 - 876
  • 10
  • [ 98-03-3 ]
  • [ 13196-35-5 ]
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[2] Tetrahedron Letters, 1999, vol. 40, # 50, p. 8887 - 8891
  • 11
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 559 - 562
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Reference: [1] Synthesis, 1991, # 6, p. 462 - 464
[2] Synthesis, 1991, # 6, p. 462 - 464
  • 13
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  • 14
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  • [ 4653-08-1 ]
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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
  • 16
  • [ 99971-34-3 ]
  • [ 68629-95-8 ]
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  • 17
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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
  • 18
  • [ 62889-07-0 ]
  • [ 88511-88-0 ]
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  • 19
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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
  • 21
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Reference: [1] Russian Journal of Applied Chemistry, 2010, vol. 83, # 8, p. 1440 - 1443
  • 22
  • [ 2786-07-4 ]
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Reference: [1] Russian Journal of Applied Chemistry, 2010, vol. 83, # 8, p. 1440 - 1443
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