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Chemical Structure| 27387-31-1
Chemical Structure| 27387-31-1
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Product Details of [ 27387-31-1 ]

CAS No. :27387-31-1 MDL No. :MFCD00173748
Formula : C13H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :HHJUJCWZKJMCLC-UHFFFAOYSA-N
M.W : 199.25 Pubchem ID :598875
Synonyms :

Calculated chemistry of [ 27387-31-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.31
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.05
TPSA : 22.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 2.03
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.27 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 1.16 mg/ml ; 0.00584 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0283 mg/ml ; 0.000142 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 27387-31-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273 UN#:N/A
Hazard Statements:H302-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 27387-31-1 ]

* 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 [ 27387-31-1 ]
  • Downstream synthetic route of [ 27387-31-1 ]

[ 27387-31-1 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 15128-52-6 ]
  • [ 4637-24-5 ]
  • [ 27387-31-1 ]
YieldReaction ConditionsOperation in experiment
71% for 1 h; Reflux A mixture of 2,3-Dihydro-1H-carbazol-4(9H)-one (1.0 mmol)and DMF-DMA (10 mmol) in DMF (5.0 mL) was refluxed for 1.0 h.The reaction mixture was cooled and extracted with ethyl acetate(2 25 mL). The organic layer was separated and washed with brine solution. The organic layer was dried over anhydrous Na2SO4.The solvent was removed under reduced pressure and the solidobtained was recrystallized from ethanol.White needles, yield 71percent, m.p. 188–90 C. IR (cm1) 1695(CO), 1H NMR (400 MHz, CDCl3) d 2.24–2.27 (t, 2H, CH2,J = 6.28 Hz), 2.56–2.59 (t, 2H, CH2, J = 6.0 Hz), 2.91–2.94 (t, 2H,CH2, J = 6.21 Hz), 3.70 (s, 3H, NCH3), 7.27–7.30 (m, 3H, Ph), 8.24–8.26 (m, 1H, Ph). Anal. Calc. for C13H13NO: C, 78.36; H, 6.58, N,7.03percent. Found: C, 78.29; H, 6.49; N, 6.92percent.
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 12, p. 1606 - 1610
[2] Journal of Molecular Structure, 2014, vol. 1080, p. 137 - 144
[3] Russian Chemical Bulletin, 2005, vol. 54, # 8, p. 1887 - 1891
  • 2
  • [ 15128-52-6 ]
  • [ 74-88-4 ]
  • [ 27387-31-1 ]
Reference: [1] Australian Journal of Chemistry, 2013, vol. 66, # 8, p. 882 - 890
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 15, p. 5211 - 5219
[3] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2557 - 2568
  • 3
  • [ 6303-88-4 ]
  • [ 27387-31-1 ]
Reference: [1] Heterocycles, 1990, vol. 30, # 2, p. 1131 - 1140
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 41, p. 9868 - 9873
  • 4
  • [ 1373402-37-9 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 18, p. 3606 - 3609
  • 5
  • [ 614-00-6 ]
  • [ 1460-08-8 ]
  • [ 27387-31-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 5, p. 1178 - 1181
  • 6
  • [ 15128-52-6 ]
  • [ 77-78-1 ]
  • [ 27387-31-1 ]
Reference: [1] Journal of Chemical Crystallography, 1995, vol. 25, # 5, p. 249 - 258
[2] Russian Chemical Bulletin, 2005, vol. 54, # 8, p. 1887 - 1891
[3] Chemistry and Industry (London, United Kingdom), 1957, p. 363
[4] Journal of the Chemical Society, 1957, p. 2227,2228
  • 7
  • [ 124907-00-2 ]
  • [ 74-88-4 ]
  • [ 27387-31-1 ]
Reference: [1] Synthesis, 2003, # 11, p. 1661 - 1666
  • 8
  • [ 57466-25-8 ]
  • [ 27387-31-1 ]
Reference: [1] Synlett, 2010, # 19, p. 2899 - 2904
  • 9
  • [ 504-02-9 ]
  • [ 27387-31-1 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2557 - 2568
[2] Organic Letters, 2016, vol. 18, # 5, p. 1178 - 1181
  • 10
  • [ 1265900-19-3 ]
  • [ 27387-31-1 ]
  • [ 1265900-36-4 ]
Reference: [1] Synlett, 2010, # 19, p. 2899 - 2904
  • 11
  • [ 56964-05-7 ]
  • [ 27387-31-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 18, p. 3606 - 3609
  • 12
  • [ 348-54-9 ]
  • [ 27387-31-1 ]
Reference: [1] Synthesis, 2003, # 11, p. 1661 - 1666
  • 13
  • [ 942-01-8 ]
  • [ 27387-31-1 ]
Reference: [1] Journal of Chemical Crystallography, 1995, vol. 25, # 5, p. 249 - 258
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 12, p. 1606 - 1610
  • 14
  • [ 39232-92-3 ]
  • [ 108-94-1 ]
  • [ 27387-31-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 41, p. 9868 - 9873
  • 15
  • [ 128266-89-7 ]
  • [ 27387-31-1 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2557 - 2568
  • 16
  • [ 27385-45-1 ]
  • [ 27387-31-1 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 2227,2228
  • 17
  • [ 7647-01-0 ]
  • [ 108367-88-0 ]
  • [ 7637-07-2 ]
  • [ 27387-31-1 ]
Reference: [1] Chemistry and Industry (London, United Kingdom), 195. 363,
  • 18
  • [ 7647-01-0 ]
  • [ 108367-88-0 ]
  • [ 64-19-7 ]
  • [ 27387-31-1 ]
Reference: [1] Chemistry and Industry (London, United Kingdom), 195. 363,
  • 19
  • [ 693-98-1 ]
  • [ 27387-31-1 ]
  • [ 51-80-9 ]
  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
81.5% With acetyl chloride In toluene; acetonitrileHeating / reflux Example 11: Synthesis of ls239-tetrahydro-9-methyl-3-[(2-methyl-lH- imidazole-1-yl methyl]-4H-carbazol-4-one To the solution of 36 ml of acetyl chloride in 50 ml of actonitrile and 750 ml of toluene, was slowly added 51 ml of N, N, N', N'- tetramethyldiaminomethane at 0°C, which was then stirred for 10min. 50 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one and 100 g of 2-methyl imidazole was subsequently added to the reaction mixture, which was then stirred under reflux. After completion of reaction, the reaction mixture was evaporated, and then 150 ml of water was added to the resulting residue. The resulting solid was filtered and washed, and then dried under a reduced pressure. The resulting solid was suspended in 350 ml of methanol, and then 0.7g of active carbon was added to thereto, which was then stirred for 1 hour under reflux. The resulting mixture was filtered and washed with methanol, which was then stirred for 3 hours at room temperature. The resulting solid was filtered and dried to give 60 g of pure white title compound (yield 81.5percent).
75%
Stage #1: at 120 - 130℃; for 8 h;
Stage #2: With sodium hydroxide In water
Example 8: Synthesis of 12s3 " 9-tetrahydro-9-methyl-3-[(2-methel-lH- imidazole-1-vl) methyl]-4H-carbazol-4-one At-10°C, 4 ml of N, N, N', N'-tetramethyldiaminomethane was slowly added to 46 ml of trifluoroacetic acid, which was then stirred for 30 min. 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one and 8 g of 2-methyl imidazole was added to the reaction mixture, which was then stirred for about 8 hours at 120-130°C. After completion of reaction, the reaction mixture was cooled at room temperature, and then IN aq. sodium hydroxide was added thereto. The resulting solid was filtered and washed with water, and then dried. The resulting solid was suspended in 80 ml of methanol, and then 0.28 g of active carbon was added thereto, which was then stirred under reflux for 1 hour. The resulting mixture was filtered and washed with methanol, and then evaporated to give 2.2 g of 1, 2,3, 9-tetrahydro-9-methyl-3-[(2-methyl-lH- imidazol-1-yl) methyl]- 4H-carbazol-4-one (yield 75percent).
66% With chloro-trimethyl-silane In DMF (N,N-dimethyl-formamide) at 90℃; for 10 h; Example 2: Synthesis of 1, 23*9-tetrahydro-9-methyl-3-r (2-methyl-lH- imidazole-1yl) methyll-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2- methyl imidazole and 2 ml of N, N, N', N'-tetramethyldiaminomethane were suspended in 20 ml of N, N-dimethylformamide, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred at 90 °C for 10 hours. 100ml of water was added to the reaction mixture. The resulting solid was filtered and dried, which was then suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 1.93 g of title compound (yield 66percent).
60% With chloro-trimethyl-silane In acetonitrile for 10 h; Heating / reflux Example 1 : Synthesis of 1, 2, 3, 9-tetrahydro-9-methyl-3-[(2-methyl-lH- imidazole-1-yl) methyll-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2- methyl imidazole and 2 ml of N, N, N', N'-tetramethyldiaminomethane were suspended in 30 ml of acetonitrile, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 40 ml of water was added to the resulting residue. The resulting solid was filtered and dried, which was then suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 1.76 g of title compound (yield 60percent).
58% With acetyl chloride In toluene for 10 h; Heating / reflux Example 7: Synthesis of 123*9-tetrahydro-9-methyl-3-r (2-methyl-lH- imidazole-1-yl methyl]-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 2 ml of N, N, N', N'-tetramethyl- diaminomethane were suspended in 30 ml of toluene, and then 1.4 ml of acetyl chloride was slowly added thereto, which was then stirred for 10 min. 1.65g of 2-methyl imidazole was added to the reaction mixture, which was then stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 150ml dichloromethane and 50ml of IN aq. sodium hydroxide were added to the resulting residue. The resulting organic layer was separated and dried over MgS04, and then evaporated. The resulting solid was suspended in acetone, which was then stirred for 3 hours, and then filtered and dried to give 1.70 g of title compound (yield 58percent).
55% With aluminum (III) chloride In acetonitrile for 10 h; Heating / reflux Example 4: Synthesis of 123, 9-tetrahydro-9-methyl-3-r (2-methyl-lH- imidazole-1-yDmethyl]-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2- methyl imidazole and 2 ml of N, N, N', N'-tetramethyldiaminomethane were suspended in 30 ml of acetonitrile, and then 1.4 g of aluminum chloride was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. 150 ml dichloromethane and 50 ml of IN aq. sodium hydroxide were added to the reaction mixture. The resulting organic layer was separated and dried over MgS04, and then evaporated. The resulting solid was suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 1.61 g of title compound (yield 55percent).

Reference: [1] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 11
[2] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 10
[3] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 7
[4] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 7
[5] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 9-10
[6] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 8
  • 20
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Reference: [1] Patent: WO2004/46116, 2004, A1, . Location in patent: Page 13
  • 21
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Reference: [1] Patent: WO2004/46116, 2004, A1, . Location in patent: Page 12
  • 22
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Reference: [1] Patent: WO2004/46116, 2004, A1, . Location in patent: Page 12-13
  • 23
  • [ 880-09-1 ]
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  • [ 27387-31-1 ]
  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
70% With aluminum (III) chloride In acetonitrile for 10 h; Heating / reflux Example 6: Synthesis of 123s9-tetrahydro-9-methyl-3-[(2-methyl-lH- imidazole-1-yl) methvl]-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2- methyl imidazole and 274 g of dipiperidinomethane were suspended in 30 ml of acetonitrile, and then 2 g of aluminum chloride was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. 150 ml dichloromethane and 50 ml of IN aq. sodium hydroxide were added to the reaction mixture. The resulting organic layer was separated and dried over MgS04, and then evaporated. The resulting solid was suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 2.05 g of title compound (yield 70percent).
68% With chloro-trimethyl-silane In DMF (N,N-dimethyl-formamide) at 90℃; for 8 h; Example 5: Synthesis of 1239-tetrahydro-9-methyl-3-r (2-methyl-lH- imidazole-l-yl . methyl]-4H-carbazol-4-one 2.0 g of 1, 2,3, 9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2- methyl imidazole and 2.74 g of dipiperidinomethane were suspended in 20 ml of N, N-dimethylformamide, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred for 8 hours at 90 °C. 100 ml of water was added to the reaction mixture. The resulting solid was filtered and dried, which was then suspended in acetone and stirred for 3 hours, and then filtered and dried under a reduced pressure to give 1.99 g of title compound (yield 68percent).
Reference: [1] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 9
[2] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 9
  • 24
  • [ 20073-50-1 ]
  • [ 693-98-1 ]
  • [ 27387-31-1 ]
  • [ 71-36-3 ]
  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
32% With methanesulfonic acid In methanol Step 1
9-Methyl-3- (2-methyl-imidazol-1ylmethyl)-1,2,3,9-tetrahydro-carbazol-4-one:
At about 70° C., a solution of 2-(oxazolidin-3-yl)ethanol (372 mg, 3.18 mmol, 1.50 equiv) and n-butanol (50 mL) was added to a mixture of 9-methyl-2,3-dihydro-1H-carbazol-4(9H)-one (420 mg, 2.11 mmol, 1.00 equiv), methanesulfonic acid (324 mg, 3.38 mmol, 1.60 equiv) and n-butanol (50 mL).
The resulting mixture was stirred at about 80° C. for about 30 minutes, and then stirred at about 120° C. for about 2.5 hours. 2-Methyl-1H-imidazole (870 mg, 10.6 mmol, 5.00 equiv) was then added to the mixture.
After stifling the mixture at about 120° C. for about 6 hours, the mixture was concentrated in vacuo and the resulting residue was resuspended in methanol.
The resulting solids were collected by filtration and washed with water and methanol.
The solids were then purified by silica gel column chromotagraphy (ethyl acetate/petroleum ether (1:1)), to give the title product as a light yellow solid (200 mg, yield=32percent).
Reference: [1] Patent: US2010/119623, 2010, A1,
  • 25
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  • [ 99614-02-5 ]
YieldReaction ConditionsOperation in experiment
54% With chloro-trimethyl-silane In toluene; acetonitrileHeating / reflux Example 10: Synthesis of 1*23*9-tetrahydro-9-methyl-3-[(2-methyl-lH- imidazole-1-yl) methel]-4H-carbazol-4-one To the solution 19.5 g of 1, 3, 5-trimethylhexahydro-1, 3,5-triazine in 20 ml of actonitrile and 150 ml of toluene, was slowly added 19 ml of chlorotrimethylsilane, which was then stirred for lOmin. lOg of 1,2, 3,9- tetrahydro-9-methyl-4H-carbazol-4-one and 8.2g of 2-methyl imidazole was subsequently added to the reaction mixture, which was then stirred under reflux. After completion of reaction, the reaction mixture was evaporated, and then 200 ml of water was added to the resulting residue, which was then stirred for 2 hours at room temperature. The resulting solid was filtered and washed with water to give 7.95 g of light yellow title compound (yield 54percent).
51% Heating / reflux Example 9: Synthesis of 12s39-tetrahydro-9-methel-3-[(2-methyl-lH- imidazole-1-yl) methyll-4H-carbazol-4-one To the solution of 7.1 ml of 1, 3, 5-trimethylhexahydro-1, 3,5-triazine in 150ml of toluene, was slowly added 4 ml of trifluoroacetic acid, which was then stirred for 10min. lOg of 1,2, 3,9-tetrahydro-9-methyl-4H-carbazol-4-one and 20 g of 2-methyl imidazole were subsequently added to the reaction mixture, which was then stirred under reflux. After completion of reaction, the reaction mixture was evaporated, and then 200 ml of water was added to the resulting residue, which was then stirred for 2 hours at room temperature. The resulting solid was filtered and washed with excess water to give 7.5 g of light yellow title compound (yield 51percent).
Reference: [1] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 11
[2] Patent: WO2005/37822, 2005, A1, . Location in patent: Page/Page column 10-11
  • 26
  • [ 123-91-1 ]
  • [ 27387-31-1 ]
  • [ 18162-48-6 ]
  • [ 99614-02-5 ]
Reference: [1] Patent: US6388091, 2002, B1,
[2] Patent: EP1207160, 2002, A1,
  • 27
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  • [ 99614-02-5 ]
  • [ 132666-57-0 ]
Reference: [1] Patent: EP1207160, 2002, A1,
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