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[ CAS No. 5650-52-2 ] {[proInfo.proName]}

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Chemical Structure| 5650-52-2
Chemical Structure| 5650-52-2
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Product Details of [ 5650-52-2 ]

CAS No. :5650-52-2 MDL No. :MFCD03426936
Formula : C7H6OS Boiling Point : -
Linear Structure Formula :- InChI Key :QHZITEHQKWPDJE-UHFFFAOYSA-N
M.W : 138.19 Pubchem ID :315614
Synonyms :

Calculated chemistry of [ 5650-52-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.29
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.37
TPSA : 45.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 1.68
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 3.5
Consensus Log Po/w : 1.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 0.942 mg/ml ; 0.00682 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.784 mg/ml ; 0.00567 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.36
Solubility : 0.609 mg/ml ; 0.00441 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 5650-52-2 ]

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 [ 5650-52-2 ]

* 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 [ 5650-52-2 ]
  • Downstream synthetic route of [ 5650-52-2 ]

[ 5650-52-2 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 16378-06-6 ]
  • [ 5650-52-2 ]
YieldReaction ConditionsOperation in experiment
30% at 20℃; for 1 h; To a suspension of P2O5 (25.4 g, 179.0 mmol) in methanesulfonic acid (100 mL) was added 3-(thiophen-3-yl)propanoic acid (5.0 g, 32.0 mmol) and the reaction was stirred at room temperature for 1 h. At completion, the reaction was concentrated and the residue was purified by flash chromatography (20-30percent EtOAc/hexane eluent) to give 4H-cyclopenta[b]thiophen-6(5H)-one (1.34 g, 30percent yield) as a brown solid. 1H NMR (300 MHz, MeOH) δ ppm 8.14 (d, J=4.8 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 2.94-3.15 (m, 4H); MS (EI) m/z=139.2 [M+1]+.
0.41 g With phosphorus pentoxide In methanesulfonic acid at 20℃; for 1 h; Step iii: 4H-cyclopentarblthiophen-6(5H)-one
To a 50 mL round bottom flask, were added phosphorous pentoxide (8.5 g, 0.0299 mol) and methanesulfonic acid (17 mL). To the same flask, 3-(thiophen-3-yl)propanoic acid (0.85 g, 0.0054 mol) was added. The reaction mixture was stirred at RT for 1 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get crude product. The crude product was purified by flash column chromatography using 30 percent ethyl acetate in hexane to get the title compound [0.41 g, 55 percent]. LC-MS: 139.1 [M+H]+.
Reference: [1] European Journal of Organic Chemistry, 2004, # 21, p. 4442 - 4451
[2] Tetrahedron, 1997, vol. 53, # 12, p. 4239 - 4246
[3] Patent: US2012/225857, 2012, A1, . Location in patent: Page/Page column 16
[4] Journal of Organic Chemistry, 1997, vol. 62, # 8, p. 2401 - 2408
[5] Journal of the Chemical Society, Chemical Communications, 1994, # 19, p. 2249 - 2250
[6] Patent: WO2015/101928, 2015, A1, . Location in patent: Page/Page column 80; 81; 82
[7] Organic Letters, 2015, vol. 17, # 21, p. 5484 - 5487
[8] Patent: US9178160, 2015, B1,
  • 2
  • [ 26359-23-9 ]
  • [ 5650-52-2 ]
YieldReaction ConditionsOperation in experiment
1.45 g With aluminum (III) chloride In 1,2-dichloro-ethane at 25℃; Reflux Synthesis of 3:
A chloroform solution of 2 (2.00 g, 12.8 mmol) in the presence of a catalytic amount of DMF (0.05 mL) was treated dropwise with thionyl chloride (1.86 mL, 25.6 mmol) under a N2 atmosphere at 25° C.
The mixture was heated under reflux for 2 hours.
The resulting dark orange solution was cooled, and concentrated in vacuo to give a brown oil.
A 1,2-dichloroethane (DCE) solution of the carboxylic acid chloride was added dropwise to a suspension of AlCl3 (1.71 g, 12.8 mmol) in DCE at 25° C.
The mixture was stirred overnight at 25° C., then heated under reflux for 2 hours, and afterwards poured into an aqueous solution of HCl (5percent).
The aqueous phase was extracted with CH2Cl2, dried over Na2SO4, and evaporated.
The residue was purified with a short silica pad (CH2Cl2) to afford cyclopenta[b]thiophen-6-one 3 as a white solid upon standing (1.45 g, yield: 82percent).
1H NMR (400 MHz, CDCl3): δ (ppm)=2.98-3.00 (m, 2H), 3.02-3.04 (m, 2H), 7.05 (d, J=4.8 Hz, 1H), 7.89 (d, J=4.8 Hz, 1H).
Reference: [1] Organic Letters, 2015, vol. 17, # 21, p. 5484 - 5487
[2] Journal of the Chemical Society, Chemical Communications, 1994, # 19, p. 2249 - 2250
[3] Journal of Organic Chemistry, 1997, vol. 62, # 8, p. 2401 - 2408
[4] Patent: US9178160, 2015, B1, . Location in patent: Page/Page column 53
  • 3
  • [ 13191-29-2 ]
  • [ 5650-52-2 ]
YieldReaction ConditionsOperation in experiment
28% With sulfuric acid In 1,2-dichloro-ethane at 20 - 80℃; for 1.25 h; To a solution of 1-(thiophen-2-yl)-prop-2-en-1-one (8.5 g; 62 mmoles) of Example 1b in 1,2-dichloroehane (47 mL) a solution of sulphuric acid (47 mL) is added dropwise at room temperature.
The mixture is then heated to 80°C for 75 minutes.
Then cooling to room temperature is carried out and the cooled liquid mass is poured in an ice bath.
An extraction with dichloromethane (2 x 20 mL) is then carried out and the organic phase washed with a 5percent NaHCO3 solution, anhydrified with sodium sulphate, filtered and concentrated under vacuum.
The obtained residue is purified by chromatography on silica gel with a ligroin/ethyl acetate mixture (elution gradient from 10percent to 80percent ethyl acetate).
After solvent removal 2.4 g of 4H-cyclopenta[b]thiophen-6(5H)-one are isolated (yellow solid; yield 28percent). Rf=0.54 (ligroin/ethyl acetate 9/7 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.89 (d, 1H, ArH), 7.05 (d, 1H, ArH), 3.01 (m, 4H, CH2); 13C NMR (CDCl3) δ (ppm): 197.3, 169.0, 141.2, 140.5, 124.0, 41.2, 24.0 FT-IR (film) νmax: 3063.8, 1668.5, 1419.1, 1248.1, 960.7, 749.8 cm-1.
28% With sulfuric acid In 1,2-dichloro-ethane at 80℃; for 1.25 h; 0254] To a solution of 1-(thiophen-2-yl)-prop-2-en-1-one (8.5 g; 62 mmoles) of Example 1b in 1,2-dichloroethane (47 mL) a solution of sulphuric acid (47 mL) is added dropwise at room temperature. The mixture is then heated to 80° C. for 75 minutes. Then cooling to room temperature is carried out and the cooled liquid mass is poured in an ice bath. An extraction with dichloromethane (2×20 mL) is then carried out and the organic phase washed with a 5percent NaHCO3 solution, anhydrified with sodium sulphate, filtered and concentrated under vacuum. The obtained residue is purified by chromatography on silica gel with a ligroin/ethyl acetate mixture (elution gradient from 10percent to 80percent ethyl acetate). After solvent removal 2.4 g of 4H-cyclopenta[b]thiophen-6(5H)-one are isolated (yellow solid; yield 28percent). Rf=0.54 (ligroin/ethyl acetate 9/7 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.89 (d, 1H, ArH), 7.05 (d, 1H, ArH), 3.01 (m, 4H, CH2); 13C NMR (CDCl3) δ (ppm): 197.3, 169.0, 141.2, 140.5, 124.0, 41.2, 24.0 FT-IR (film) νmax: 3063.8, 1668.5, 1419.1, 1248.1, 960.7, 749.8 cm−1
Reference: [1] Patent: EP2789619, 2014, A1, . Location in patent: Paragraph 0097
[2] Patent: US2014/343294, 2014, A1, . Location in patent: Paragraph 0253; 0254
  • 4
  • [ 849769-14-8 ]
  • [ 5650-52-2 ]
YieldReaction ConditionsOperation in experiment
42% With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Tri(p-tolyl)phosphine In toluene for 16 h; Reflux To a stirring solution of compound 1 (1 g, 4.8 mmol) in dry toluene (80 mL) was added [Rh(cod)2](BF4) (0.39 g, 0.96 mmol), tri-p-tolylphosphine(1.17 g, 3.84 g), 2,2,6,6- tetramethylpiperidine (0.68 g, 4.8 mmol) at room temperature. The reaction mixture was stirred at reflux for 16 h then concentrated and purified by silica gel column chromatography eluting with12percent EtOAc/Hexane to afford compound 2 (0.28 g,42percent). TLC: 20percent EtOAc/Hexane (Rf: 0.3)
Reference: [1] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 583
  • 5
  • [ 21980-45-0 ]
  • [ 5650-52-2 ]
YieldReaction ConditionsOperation in experiment
38% With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Tri(p-tolyl)phosphine In toluene for 16 h; Reflux To a stirring solution of compound 1 (1 g, 4.8 mmol) in dry toluene (80 mL) was added [Rh(cod)2](BF4) (0.39 g, 0.96 mmol), trip-tolylphosphine(1.17 g, 3.84 g), 2,2,6,6- tetramethylpiperidine (0.68 g, 4.8 mmol) at room temperature. The reaction mixture was stirred at reflux for 16 h then concentrated and purified by silica gel column chromatography eluting with 12percent EtOAc/Hexane to afford compound 2 (0.25 g,38percent). TLC: 20percent EtOAc/Hexane (Rf: 0.3)
Reference: [1] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 584
  • 6
  • [ 21980-45-0 ]
  • [ 5650-52-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3248 - 3249
  • 7
  • [ 1195-52-4 ]
  • [ 5650-52-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 8, p. 2401 - 2408
[2] Journal of the Chemical Society, Chemical Communications, 1994, # 19, p. 2249 - 2250
[3] Patent: US9178160, 2015, B1,
  • 8
  • [ 1195-52-4 ]
  • [ 5650-52-2 ]
Reference: [1] European Journal of Organic Chemistry, 2004, # 21, p. 4442 - 4451
[2] Patent: WO2015/101928, 2015, A1,
  • 9
  • [ 616-44-4 ]
  • [ 5650-52-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 12, p. 4239 - 4246
[2] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 10
  • [ 34846-44-1 ]
  • [ 5650-52-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 12, p. 4239 - 4246
  • 11
  • [ 26415-26-9 ]
  • [ 5650-52-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 12, p. 4239 - 4246
  • 12
  • [ 26415-25-8 ]
  • [ 5650-52-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 12, p. 4239 - 4246
  • 13
  • [ 40570-64-7 ]
  • [ 5650-52-2 ]
Reference: [1] Patent: EP2789619, 2014, A1,
[2] Patent: US2014/343294, 2014, A1,
  • 14
  • [ 498-62-4 ]
  • [ 5650-52-2 ]
Reference: [1] Patent: WO2015/101928, 2015, A1,
[2] Patent: WO2016/44770, 2016, A1,
  • 15
  • [ 13191-36-1 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 16
  • [ 98-03-3 ]
  • [ 5650-52-2 ]
Reference: [1] Patent: WO2016/44770, 2016, A1,
  • 17
  • [ 121792-93-6 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 18
  • [ 121792-91-4 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 19
  • [ 13191-37-2 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 20
  • [ 13191-40-7 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 21
  • [ 121792-92-5 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 22
  • [ 189179-83-7 ]
  • [ 5650-52-2 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1989, vol. 86, # 1, p. 93 - 98
  • 23
  • [ 5650-52-2 ]
  • [ 960289-03-6 ]
Reference: [1] Patent: US2012/225857, 2012, A1,
[2] Patent: WO2007/146759, 2007, A2,
[3] Patent: WO2007/146758, 2007, A2,
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