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[ CAS No. 104618-32-8 ] {[proInfo.proName]}

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Chemical Structure| 104618-32-8
Chemical Structure| 104618-32-8
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Product Details of [ 104618-32-8 ]

CAS No. :104618-32-8 MDL No. :MFCD00158659
Formula : C14H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PWUJQPNLEZZILN-UHFFFAOYSA-N
M.W : 243.26 Pubchem ID :11998391
Synonyms :

Calculated chemistry of [ 104618-32-8 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.84
TPSA : 54.45 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) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.771 mg/ml ; 0.00317 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 1.24 mg/ml ; 0.0051 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0982 mg/ml ; 0.000404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 104618-32-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104618-32-8 ]

* 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 [ 104618-32-8 ]
  • Downstream synthetic route of [ 104618-32-8 ]

[ 104618-32-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 104618-31-7 ]
  • [ 104618-32-8 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In ethyl acetate at 5 - 20℃; EXAMPLE 1: 4- (Phthalimido) -cyclohexanone [0034] 4- (Phthalimido) -cyclohexanol (146 g) was mixed with AcOEt (1000 mL) , after which and NaBr (8 g) and TEMPO(0.5 g) was added. 1000 mL of NaClO (10 percent) was added in portions and the reaction mixture was adjusted using NaHCψ3 to pH 7- 8 to maintain the temperature between 5 and 20 0C. After the reaction was completed, the aqueous layer was separated and the organic layer was washed with brine (400 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to give the product as white solid (95 percent yield) .
92.4% With potassium dichromate; sulfuric acid In chloroform; water at 25℃; for 4 h; 190gms(0.7755mole) 4-phthalimido cyclohexanol are dissolve in 1480ml chloroform.Add solution of H2SO4 (435.87gm, 4.4476mole cone. H2SO4 was added in 900 mlwater). Cool mass to 25°C,add lot wise 180.5gm(0.6139mole) potassium dichromate inone hour. Stir mass for three hours, add 900 ml water and separate organic phase.Organic phase was washed with water and 2percent NaHCO3 solution, after drying andconcentration of extracts product was isolated by adding methanol and water mixture.YIELD: 175g(92.4percent)PURITY: 96.01percent.
88% With pyridinium chlorochromate In dichloromethane at 20℃; for 26 h; The title compound from Step A above (28 g, 114 mmol) was dissolved in dichloromethane (990 mL) and pyridinium chlorochromate (33.6 g, 157 mmol) was added in portions. The reaction mixture was stirred at room temperature for 8 h. Then another batch of pyridinium chlorochromate (10.4 g, 48.6 mmol) was added in portions and stirring at room temperature was continued for 18 h. The reaction mixture was filtered through a pad of Celite and the Celite pad was washed with dichlormethane (400 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) as a mobile phase to afford the title compound as a white solid (24.62 g, 88percent)1H-NMR (400 MHz, CDCl3): δ=2.17-2.24 (m, 2H), 2.60-2.71 (m, 4H), 2.80-2.90 (m, 2H), 4.78 (tt, 1H), 7.84-7.88 (m, 2H), 7.97-8.02 (m, 2H)
65% With pyridinium chlorochromate In dichloromethane Step 2
A solution of 2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (3.10 g, 12.6 mmol) in CH2Cl2 (25.0 mL) was added to a slurry of PCC (4.10 g, 19.0 mmol) in CH2Cl2 (15.0 mL) and stirred at room temperature for 3.5 hours.
The reaction was diluted with Et2O (60.0 mL), decanted and the residue swirled with Et2O (2*40.0 mL).
The combined ether layers were filtered through florisil and concentrated in vacuo to dryness, and the residue was recrystallized from ethyl acetate/hexane to give 2.01 g (65percent) of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione as colorless needles: mp 140.3-142.1° C.; 1H NMR (400 MHz, CDCl3) δ7.84, 7.74, 4.64, 2.72, 2.54, 2.09; 13C NMR (100 MHz, CDCl3) δ208.9, 168.1, 134.1, 131.9, 123.3, 48.4, 39.9, 28.6; IR (mull) 3062, 3031, 2958, 2949, 2919, 2885, 1775, 1762, 1721, 1708, 1611, 1465, 1436, 1419, 1393, 1379, 719 cm-1; HRMS (FAB) calcd for C14H14NO3: 244.0974, found 244.0976; Anal. Calcd for C-14H14NO3: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.87; H, 5.47; N, 5.73.

Reference: [1] Patent: WO2010/78250, 2010, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2006/3677, 2006, A1, . Location in patent: Page/Page column 10; 16
[3] Patent: US2011/280808, 2011, A1, . Location in patent: Page/Page column 62
[4] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
[5] Patent: US2003/100596, 2003, A1,
[6] Patent: US5827871, 1998, A,
[7] Patent: US5464864, 1995, A,
[8] Patent: EP603432, 1994, A1,
[9] Patent: US4731374, 1988, A,
[10] Patent: WO2008/41240, 2008, A1, . Location in patent: Page/Page column 16-17
  • 2
  • [ 1252607-42-3 ]
  • [ 104618-32-8 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid In tetrahydrofuran; water at 115℃; for 2 h; The title compound from Step B above (3.5 g, 12.1 mmol) was suspended in tetrahydrofurane (30 mL) and water (20 mL). After the addition of p-toluene sulfonic acid (0.13 g, 0.67 mmol), the mixture was heated at 115° C. in a sand-bath for 2 h. The mixture was diluted with ethyl acetate (200 mL) and an aqueous solution of sodium bicarbonate was added until pH8-9. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (3.x.50 mL). The combined organic phase was dried over Na2SO4, filtered and the solvent was removed to afford the title compound as an off-white solid (3 g, quant.).1H-NMR (400 MHz, CDCl3): δ=2.17-2.24 (m, 2H), 2.60-2.71 (m, 4H), 2.80-2.90 (m, 2H), 4.78 (tt, 1H), 7.84-7.88 (m, 2H), 7.97-8.02 (m, 2H)
Reference: [1] Patent: US2011/280808, 2011, A1, . Location in patent: Page/Page column 59
  • 3
  • [ 99337-98-1 ]
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Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 314 - 322
  • 4
  • [ 22509-74-6 ]
  • [ 104618-32-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 314 - 322
[2] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
[3] Patent: US2011/280808, 2011, A1,
[4] Journal of the American Chemical Society, 2011, vol. 133, # 46, p. 18534 - 18537
  • 5
  • [ 27489-62-9 ]
  • [ 104618-32-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 314 - 322
  • 6
  • [ 6850-65-3 ]
  • [ 104618-32-8 ]
Reference: [1] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
  • 7
  • [ 22428-87-1 ]
  • [ 104618-32-8 ]
Reference: [1] Patent: US2011/280808, 2011, A1,
  • 8
  • [ 4746-97-8 ]
  • [ 104618-32-8 ]
Reference: [1] Patent: US2011/280808, 2011, A1,
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