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[ CAS No. 155694-84-1 ] {[proInfo.proName]}

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Chemical Structure| 155694-84-1
Chemical Structure| 155694-84-1
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Product Details of [ 155694-84-1 ]

CAS No. :155694-84-1 MDL No. :MFCD22573024
Formula : C9H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UPVDTZDVDGTUEP-UHFFFAOYSA-N
M.W : 179.17 Pubchem ID :21782322
Synonyms :

Calculated chemistry of [ 155694-84-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.42
TPSA : 62.89 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.15 mg/ml ; 0.0064 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.478 mg/ml ; 0.00267 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.5
Solubility : 0.567 mg/ml ; 0.00316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 155694-84-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 155694-84-1 ]

* 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 [ 155694-84-1 ]
  • Downstream synthetic route of [ 155694-84-1 ]

[ 155694-84-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 155694-84-1 ]
  • [ 122710-21-8 ]
Reference: [1] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224
[2] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 72-73
  • 2
  • [ 1449199-73-8 ]
  • [ 155694-84-1 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With ozone In methanol; dichloromethane at -78℃; for 3 h;
Stage #2: With dimethylsulfide In methanol; dichloromethane at 20℃;
Example 22
Preparation of 1-(4-methyl-2-nitrophenyl)ethan-1-one (C84)
To a reaction flask were added 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (11.4 g, 64.3 mmol), dichloromethane (292 mL), and methanol (29.2 mL).
The reaction mixture was cooled to -78° C.
Ozone was bubbled into the reaction mixture, and the reaction mixture was stirred at -78° C. for 3 hours.
The reaction mixture was flushed with nitrogen.
Dimethylsulfide (14.0 mL, 189 mmol) was added, and the reaction mixture was allowed to stir and warm to room temperature overnight.
The reaction was concentrated.
Purification by flash column chromatography using ethyl acetate/hexanes as eluent provided the title compound as an oil (8.90 g, 70percent): 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, J=1.7, 0.8 Hz, 1H), 7.50 (ddd, J=7.8, 1.7, 0.8 Hz, 1H), 7.35 (dd, J=7.7, 0.9 Hz, 1H), 2.53 (s, 3H), 2.48 (s, 3H).
70%
Stage #1: With ozone In methanol; dichloromethane at -78℃; for 3 h;
Stage #2: With dimethylsulfide In methanol; dichloromethane at 20 - 24℃; Inert atmosphere
To a reaction flask were added 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (11.4 g, 64.3 mmol), dichloromethane (292 mL), and methanol (29.2 mL). The reaction mixture was cooled to -78 °C. Ozone was bubbled into the reaction mixture, and the reaction mixture was stirred at -78 °C for 3 hours. The reaction mixture was flushed with nitrogen. Dimethylsulfide (14.0 mL, 189 mmol) was added, and the reaction mixture was allowed to stir and warm to room temperature overnight. The reaction was concentrated. Purification by flash column chromatography using ethyl acetate/hexanes as eluent provided the title compound as an oil (8.90 g, 70percent) : 1H NMR (300 MHz, CDCI3) δ 7.85 (dt, J = 2.0, 1.0 Hz, 1H), 7.50 (ddt, J = 7.8, 1.7, 0.8 Hz, 1H), 7.35 (dd, J = 7.7, 0.9 Hz, 1H), 2.57 - 2.51 (m, 3H), 2.49 (q, J = 0.9 Hz, 3H).
70% With ozone In methanol; dichloromethane at -78℃; for 3 h; Inert atmosphere Example 15
Preparation of 1-(4-methyl-2-nitrophenyl)ethan-1-one (C55)
To a reaction flask were added 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (11.4 g, 64.3 mmol), dichloromethane (292 mL), and methanol (29.2 mL).
The reaction mixture was cooled to -78° C.
Ozone was bubbled into the reaction mixture, and the reaction mixture was stirred at -78° C. for 3 hours.
The reaction mixture was flushed with nitrogen.
Dimethylsulfide (14.0 mL, 189 mmol) was added, and the reaction mixture was allowed to stir and warm to room temperature overnight.
The reaction was concentrated.
Purification by flash column chromatography using ethyl acetate/hexanes as eluent provided the title compound as an oil (8.90 g, 70percent): 1H NMR (300 MHz, CDCl3) δ 7.85 (dt, J=2.0, 1.0 Hz, 1H), 7.50 (ddt, J=7.8, 1.7, 0.8 Hz, 1H), 7.35 (dd, J=7.7, 0.9 Hz, 1H), 2.57-2.51 (m, 3H), 2.49 (q, J=0.9 Hz, 3H).
Reference: [1] Patent: US2017/64962, 2017, A1, . Location in patent: Paragraph 0627; 0628
[2] Patent: WO2017/40194, 2017, A1, . Location in patent: Page/Page column 91
[3] Patent: US2017/66757, 2017, A1, . Location in patent: Paragraph 0488; 0489
  • 3
  • [ 1439930-68-3 ]
  • [ 155694-84-1 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5932 - 5948
  • 4
  • [ 861523-96-8 ]
  • [ 155694-84-1 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 2185
  • 5
  • [ 861523-96-8 ]
  • [ 7732-18-5 ]
  • [ 155694-84-1 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 2185
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