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[ CAS No. 1190360-23-6 ] {[proInfo.proName]}

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Chemical Structure| 1190360-23-6
Chemical Structure| 1190360-23-6
Structure of 1190360-23-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1190360-23-6 ]

CAS No. :1190360-23-6 MDL No. :MFCD28955974
Formula : C15H13Br Boiling Point : -
Linear Structure Formula :- InChI Key :VECLPBKDHAALGQ-UHFFFAOYSA-N
M.W : 273.17 Pubchem ID :59629661
Synonyms :

Calculated chemistry of [ 1190360-23-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.09
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.06
Log Po/w (XLOGP3) : 5.11
Log Po/w (WLOGP) : 4.76
Log Po/w (MLOGP) : 4.92
Log Po/w (SILICOS-IT) : 5.16
Consensus Log Po/w : 4.6

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.31
Solubility : 0.00134 mg/ml ; 0.00000492 mol/l
Class : Moderately soluble
Log S (Ali) : -4.85
Solubility : 0.00382 mg/ml ; 0.000014 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.8
Solubility : 0.0000432 mg/ml ; 0.000000158 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 1190360-23-6 ]

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 [ 1190360-23-6 ]

* 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 [ 1190360-23-6 ]
  • Downstream synthetic route of [ 1190360-23-6 ]

[ 1190360-23-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 2038-91-7 ]
  • [ 74-88-4 ]
  • [ 1190360-23-6 ]
YieldReaction ConditionsOperation in experiment
96% With sodium t-butanolate In dimethyl sulfoxide at 80 - 90℃; for 0.5 h; 37 g (152 mmol) of 3-bromo-9H-fluorene are dissolved in 600 ml of dry DMSO in a flask dried by heating. 43.9 g (457 mmol) of NaOtBu are added at room temperature. Let the blue suspension now have an internal temperature of 80 ° C. At this temperature, 64.8 g (457 mmol) of iodomethane are added dropwise to the purplish solution at a rate that does not exceed an internal temperature of 90 deg. C (duration: about 30 minutes). The batch is kept at an internal temperature of 80-90 ° C for an additional 30 minutes, then poured into 1500 ml of ice water and stirred for about 20 minutes. The precipitated solid is filtered off with suction and washed successively with about 200 ml of H2O and methanol. Yield: 39 g (144 mmol), 96percent of theory; Purity: 95percent by'H-NMR.
95% With sodium t-butanolate In dimethyl sulfoxide at 20 - 65℃; for 1 h; 29.5 g (120 millimol) of 3-bromo-9H-fluorene (Tetrahedron Letters, 51, 37, 4894-4897; 2010) is dissolved in 220 ml of anhydrous DMSO in the flask dried by heating. 34.7 g (361 millimol) NaOt Bu is added at room temperature. Suspension is made into the internal temperature of 65 degrees C. 22.5 ml (361 millimol) iodomethane solution in DMSO (50 ml) was added at this internal temperature which does not exceed 65 degrees C (period: for about 30 minutes). A batch is maintained with the degree of internal temperature of 65 degrees C for further 30 minutes. Then, it flows into the 400-ml well cold aqueous Na4OH solution (1/1, v/v), and stirred for about 20 minutes. Suction filtration of the precipitating solid is carried out, and washed continuously with about 200 ml of H2O and methanol. Yield: 31g (114 millimol) (95percent of a theoretical value).
65 mmol With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 80 - 90℃; (6) take the product 70mmol, add solvent DMSO, potassium tert-butanol 280mmol,80 degrees Celsius stirring 1h. Dropping methyl iodide 280 mmol,The temperature was raised to 90 ° C and the reaction was carried out overnight to obtain 65 mmol of product.
30 g With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 80 - 90℃; for 0.5 h; A mixture of 37 g (152 mmol) of 17-0Was dissolved in 600 ml of DMSO at room temperature,43.9 g (457 mmol) of potassium t-butoxide was added and the temperature was raised to 80 ° C.64.8 g (457 mmol) of methyl iodide was added dropwise to control the temperature not to exceed 90 ° C.At 80-90 ° C for 30 min, add 1000 ml of water, stir,The precipitated solid was washed with water and methanol. To obtain product 17-1 30g.

Reference: [1] Patent: KR2017/59015, 2017, A, . Location in patent: Paragraph 0229-0231
[2] Patent: JP2015/530364, 2015, A, . Location in patent: Paragraph 0160; 0161
[3] Patent: CN106748967, 2017, A, . Location in patent: Paragraph 0052; 0063
[4] Patent: CN107090003, 2017, A, . Location in patent: Paragraph 0075; 0078
  • 2
  • [ 191103-21-6 ]
  • [ 75-16-1 ]
  • [ 1190360-23-6 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 0 - 20℃; for 3 h; Inert atmosphere
Stage #2: With hydrogenchloride; acetic acid In water for 10 h; Reflux
Add (15 g, 52 mmol) and 100 mL of tetrahydrofuran in a dry 300 mL round-bottom flask reactor under nitrogen atmosphere and add methylmagnesium bromide (10 mL, 300 mmol) dropwise at 0 ° C.After completion of dropwise addition, the mixture is stirred at room temperature for 3 hours.After completion of the reaction, add 100 mL of 2 N HCl aqueous solution at 0 ° C and stir for 30 minutes.The layers were separated with ethyl acetate, and the organic layer was concentrated. Immediately, 100 mL of acetic acid and 10 mL of hydrochloric acid were added, and the mixture was refluxed with stirring for 10 hours.After completion of the reaction, an excess amount of water was added, and the mixture was stirred for 30 minutes, and then filtered. The resultant was separated by column chromatography to obtain (12.1 g, 86percent).
Reference: [1] Patent: KR2018/14985, 2018, A, . Location in patent: Paragraph 0397-0402
  • 3
  • [ 1093418-75-7 ]
  • [ 1190360-23-6 ]
Reference: [1] Patent: KR2018/14985, 2018, A,
  • 4
  • [ 98-80-6 ]
  • [ 1190360-23-6 ]
Reference: [1] Patent: KR2018/14985, 2018, A,
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