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[ CAS No. 196597-78-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 196597-78-1
Chemical Structure| 196597-78-1
Chemical Structure| 196597-78-1
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Product Details of [ 196597-78-1 ]

CAS No. :196597-78-1 MDL No. :MFCD09955085
Formula : C11H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZZUIZMWFNOKNLN-UHFFFAOYSA-N
M.W : 174.20 Pubchem ID :11137616
Synonyms :

Calculated chemistry of [ 196597-78-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.83
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 3.34
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.31
Solubility : 0.846 mg/ml ; 0.00486 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.54 mg/ml ; 0.0146 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.4
Solubility : 0.0689 mg/ml ; 0.000395 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 196597-78-1 ]

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

Application In Synthesis of [ 196597-78-1 ]

* 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 [ 196597-78-1 ]
  • Downstream synthetic route of [ 196597-78-1 ]

[ 196597-78-1 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 196597-77-0 ]
  • [ 196597-78-1 ]
YieldReaction ConditionsOperation in experiment
88.6% With hydrogen; sodium acetate In methanol at 40℃; for 8 h; 4,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (280 kg, 843mol), anhydrous sodium acetate (173 kg, 2109 mol), methanol (6384 L) were mixed, and the reaction system was replaced with nitrogen. Then, to the reaction mixture was added 10percent Pd/C (30.8 kg, as dry weight), and pressurized with hydrogen to 0.29 to 0.49 MPa, and catalytically reduced at about 40°C for 8 hrs with stirring at such a stirring rate that the gas-liquid overall mass transfer coefficient KLa(1/hr) is about 15. The catalyst was filtered, and the filtrate was concentrated under reduced pressure, and further water was added to the residue, followed by concentrating under reduced pressure to substitute the solvent, cooling and stirring for 1 hr to mature. The crystallization solution was filtered to give wet crystals of title compound (amount 127 kg as dry weight, yield 86.6percent). The content of dimer in the wet crystals was less than 0.1percent by weight.
83% With sodium acetate In methanol Reference Example 6
1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one
To a suspension of 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (18.4 g, 55.4 mmols) in methanol (400 mL) was added 10percent Palladium on activated carbon (2.0 g, 50percent hydrous) followed by sodium acetate (12.6 g, 154 mmols).
The mixture was stirred at 40° C. for 1.5 hours under hydrogen atmosphere (4 kgf/cm2).
The catalyst was filtered off and the filtrate was concentrated under reduced pressure.
Crystals were collected by filtration, washed with water and recrystallized successively with methanol:water=5:1 to obtain 8.0 g (yield: 83percent) of the title compound.
83% With hydrogen; sodium acetate In methanol; acetic acid at 20℃; for 2 h; To a suspension of 4,5-dibromo-l,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (720 g, 2.15 moles) in methanol (6.60 lit.) and acetic acid (1.5 lit.) was added 10percent palladium on activated carbon (150 g, 50percent hydrous) followed by addition of sodium acetate (500 g, 6.09 moles). The reaction mixture was stirred at room temperature for 2 hours under hydrogen atmosphere (5 kg/cm2). After the completion of reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystals were collected by filtration, washed with water (3 lit.) and recrystallized with methanol-water (5:1) to obtain 318 g (83percent yield) of the title compound.
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[2] Patent: EP1199304, 2002, A1, . Location in patent: Referential example 18
[3] Patent: EP1792899, 2007, A1, . Location in patent: Page/Page column 13
[4] Patent: CN103570651, 2016, B, . Location in patent: Paragraph 0063; 0064
[5] Patent: US6348485, 2002, B1,
[6] Patent: WO2010/41271, 2010, A2, . Location in patent: Page/Page column 30
[7] Patent: EP1334732, 2003, A1,
[8] Patent: US2004/18239, 2004, A1,
[9] Patent: US10098866, 2018, B2,
[10] Patent: WO2008/150953, 2008, A1, . Location in patent: Page/Page column 32
[11] Patent: WO2008/150953, 2008, A1, . Location in patent: Page/Page column 32
  • 2
  • [ 15480-25-8 ]
  • [ 196597-78-1 ]
YieldReaction ConditionsOperation in experiment
62% With hydrogen In tetrahydrofuran; ethanol at 35℃; for 24 h; 6,7-dihydro-8H-indeno-[5,4-b]furan-8-one of the formula (IV) (2.0 g, 11.6 mmol) was dissolved in a solvent mixture (40 ml ethanol, 20 ml tetrahydrofuran and 12 drops of triethylamine). The stirred solution was hydrogenated for 24 hours at 35 °C/0.6-0.7 MPa over Pd-C (500 mg, 5 percent Pd-C (w/w)). The progress of reaction was monitored with HPLC. After the reaction was completed, the hydrogen gas was released, Pd-C was filtered off and the product was washed with 20 ml THF. After removal of the solvent under vacuum, recrystallization from ethanol afforded 1 ,2,6,7-tetrahydro-8 - -indeno- [5,4-b]furan-8-one of the formula (I) as light yellow solid (yield 62 percent, 99.6 HPLC purity). 1H NMR (CDCI3, 400 MHz), δ: 7.22 (d, J = 8.4 Hz, H), 7.03 (d, J = 8.4 Hz, 1 H), 4.67 (t, J = 8.8 Hz, 2H), 3.49 (t, J = 8.8 Hz, 2H,), 3.10 (t, J = 5.2 Hz, 2H), 2.70 (t, J = 5.2 Hz, 2H) 13C NMR (CDCI3, 100 MHz), δ: 207.42, 160.25, 147.11 , 133.68, 125.62, 123.93, 115.63, 72.34, 37.16, 28.41 , 25.40Retention time (LC/MS), min: 8.38; MS (MH+), m/z: 173; Molecular weight, g/mol: 174.
Reference: [1] Patent: WO2011/44990, 2011, A1, . Location in patent: Page/Page column 9
  • 3
  • [ 196597-77-0 ]
  • [ 1092507-06-6 ]
  • [ 1092507-07-7 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2008/151170, 2008, A2, . Location in patent: Page/Page column 5; 7; 15; 23; 38; 47-48; 69
  • 4
  • [ 50-00-0 ]
  • [ 1205098-82-3 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2010/115897, 2010, A2, . Location in patent: Page/Page column 18
  • 5
  • [ 496-16-2 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[3] Patent: WO2008/150953, 2008, A1,
[4] Patent: WO2008/150953, 2008, A1,
[5] Patent: WO2008/151170, 2008, A2,
  • 6
  • [ 55745-70-5 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[2] Patent: WO2008/150953, 2008, A1,
[3] Patent: WO2008/150953, 2008, A1,
[4] Patent: WO2008/151170, 2008, A2,
  • 7
  • [ 196597-76-9 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[2] Patent: WO2008/150953, 2008, A1,
[3] Patent: WO2008/151170, 2008, A2,
  • 8
  • [ 196597-66-7 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
[2] Patent: WO2008/150953, 2008, A1,
  • 9
  • [ 1205098-83-4 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2010/7022, 2010, A1, . Location in patent: Page/Page column 12-13
[2] Patent: WO2010/92107, 2010, A1, . Location in patent: Page/Page column 16-17; 21-22
  • 10
  • [ 196597-65-6 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
  • 11
  • [ 196597-67-8 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
  • 12
  • [ 227179-21-7 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
  • 13
  • [ 196597-75-8 ]
  • [ 196597-78-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239
  • 14
  • [ 198707-57-2 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2008/150953, 2008, A1,
[2] Patent: WO2008/151170, 2008, A2,
  • 15
  • [ 62803-47-8 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2011/44990, 2011, A1,
  • 16
  • [ 1290145-09-3 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2011/44990, 2011, A1,
  • 17
  • [ 217483-05-1 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2008/150953, 2008, A1,
  • 18
  • [ 1198465-69-8 ]
  • [ 196597-78-1 ]
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 309 - 314
  • 19
  • [ 1198465-72-3 ]
  • [ 196597-78-1 ]
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 309 - 314
  • 20
  • [ 215057-28-6 ]
  • [ 196597-78-1 ]
Reference: [1] Patent: WO2008/151170, 2008, A2,
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