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Chemical Structure| 209984-30-5
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Product Details of [ 209984-30-5 ]

CAS No. :209984-30-5 MDL No. :MFCD11977772
Formula : C15H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :VLYOZVMUFWIJIQ-UHFFFAOYSA-N
M.W : 223.27 Pubchem ID :46856420
Synonyms :

Calculated chemistry of [ 209984-30-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.07
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.87
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.37
Solubility : 0.0948 mg/ml ; 0.000425 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.494 mg/ml ; 0.00221 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.08
Solubility : 0.00184 mg/ml ; 0.00000822 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 209984-30-5 ]

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

Application In Synthesis of [ 209984-30-5 ]

* 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 [ 209984-30-5 ]
  • Downstream synthetic route of [ 209984-30-5 ]

[ 209984-30-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 20011-90-9 ]
  • [ 74-88-4 ]
  • [ 209984-30-5 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1 h;
Stage #2: for 17 h;
Step A
- Synthesis of 7-Methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one
A round bottom flask was charged with sodium hydride (0.295 g, 7.46 mmol) in 9.0 ml of DMF and treated with 5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.3 g, 6.22 mmol) (CAS # 20011-90-9, prepared as described in) and references cited therein).
After stirring at 60°C for 1 h, the solution was treated with methyl iodide (1.16 ml, 18.6 mmol) and stirring continued for 17 h with the exclusion of light.
After cooling, the reaction was diluted with CH2Cl2/H2O, washed with NaHSO4 solution, H2O, and dried over Na2SO4.
Evaporation and flash chromatography (SiO2, CHCl3) gave 0.885 g (63percent) of the title compound as a colorless solid.
NMR data was as follows:
1H-nmr (CDCl3): δ = 7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H).
C15H13NO(MW = 223.27); mass spectroscopy (MH+) 223.
Anal. Calcd for C15H13NO; C, 80.69 H, 5.87 N, 6.27. Found: C, 80.11 H, 5.95 N, 6.23.
63%
Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 60℃; for 1 h;
Stage #2: for 17 h;
A round bottom flask was charged with sodium hydride (0.295 g, 7.46 mmol) in 9.0 mL of DMF and treated with 5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.3 g, 6.22 mmol) (CAS No. 20011-90-9, prepared as described in R. F. C. Brown, et. al., Tetrahedron Letters 1971, 8, 667-6709 and references cited therein). After stirring at 60° C. for 1 h, the solution was treated with methyl iodide (1.16 mL, 18.6 mmol) and stirring continued for 17 h with the exclusion of light. After cooling, the reaction was diluted with CH2Cl2/H2O, washed with NaHSO4 solution, H2O, and dried over Na2SO4. Evaporation and flash chromatography (SiO2, CHCl3) gave 0.885 g (63percent) of the title compound as a colorless solid.Physical data were as follows:1H-NMR (CDCl3): δ=7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H).C15H13NO (MW=223.27); mass spectroscopy (MH+) 223.Anal. Calcd for C15H13NO; C, 80.69 H, 5.87 N, 6.27. Found: C, 80.11 H, 5.95 N, 6.23.
Reference: [1] Organic Letters, 2008, vol. 10, # 21, p. 4871 - 4874
[2] Journal of Organic Chemistry, 2010, vol. 75, # 17, p. 5984 - 5993
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6392 - 6395
[4] Patent: EP951466, 2009, B1, . Location in patent: Page/Page column 72
[5] Patent: US6958330, 2005, B1, . Location in patent: Page/Page column 38-39
[6] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 2
  • [ 955879-95-5 ]
  • [ 209984-30-5 ]
YieldReaction ConditionsOperation in experiment
59% at 100 - 170℃; for 1 h; Inert atmosphere In a perfectly dried three-necked flask, aluminum chloride (4 eq.) was added portion wise to 23 under a nitrogen stream. The mixture was vigorously stirred and heated at 100 °C for 1 h and then the temperature was raised to 170 °C until gas evolution ceased. After removing the oil bath, ice was added and the mixture was vigorously stirred foradditional 30 min, then HCl 2N was added. The aqueous layer was extracted exhaustively withchloroform. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated.The crude product was recrystallized from EtOH; Rf: 0.55 (n-hexane/EtOAc 98:2); yield: 59percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5918 - 5923
[2] Molecules, 2013, vol. 18, # 9, p. 10747 - 10767
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 11, p. 1262 - 1266
  • 3
  • [ 1243327-76-5 ]
  • [ 1484-12-4 ]
  • [ 209984-30-5 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6445 - 6451
  • 4
  • [ 40400-15-5 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 5
  • [ 615-36-1 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 6
  • [ 90-41-5 ]
  • [ 209984-30-5 ]
Reference: [1] Molecules, 2013, vol. 18, # 9, p. 10747 - 10767
  • 7
  • [ 14925-09-8 ]
  • [ 209984-30-5 ]
Reference: [1] Molecules, 2013, vol. 18, # 9, p. 10747 - 10767
  • 8
  • [ 325141-76-2 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 9
  • [ 683277-81-8 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 10
  • [ 683277-82-9 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
  • 11
  • [ 683277-83-0 ]
  • [ 209984-30-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2323 - 2326
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