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[ CAS No. 159-66-0 ] {[proInfo.proName]}

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Chemical Structure| 159-66-0
Chemical Structure| 159-66-0
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Product Details of [ 159-66-0 ]

CAS No. :159-66-0 MDL No. :MFCD08704216
Formula : C25H16 Boiling Point : -
Linear Structure Formula :- InChI Key :SNFCXVRWFNAHQX-UHFFFAOYSA-N
M.W : 316.40 Pubchem ID :135975
Synonyms :

Calculated chemistry of [ 159-66-0 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.04
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 102.74
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.49
Log Po/w (XLOGP3) : 6.37
Log Po/w (WLOGP) : 6.03
Log Po/w (MLOGP) : 7.0
Log Po/w (SILICOS-IT) : 6.58
Consensus Log Po/w : 5.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.53
Solubility : 0.0000944 mg/ml ; 0.000000298 mol/l
Class : Poorly soluble
Log S (Ali) : -6.16
Solubility : 0.000218 mg/ml ; 0.00000069 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.18
Solubility : 0.0000000208 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.52

Safety of [ 159-66-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 159-66-0 ]

* 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 [ 159-66-0 ]
  • Downstream synthetic route of [ 159-66-0 ]

[ 159-66-0 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 159-66-0 ]
  • [ 67665-47-8 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[3] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
  • 2
  • [ 67665-44-5 ]
  • [ 159-66-0 ]
YieldReaction ConditionsOperation in experiment
95% With iron(III) chloride In nitromethane at 20℃; for 0.0833333 h; General procedure: Compound 1a (130 mg, 0.5 mmol) was taken in a 5 mL round bottom flask containing 1 mL of dry nitromethane solvent. Anhydrous FeCl3 (5 mg, 0.025 mmol) was added and the resulting solution was stirred at room temperature for 5 min. After completion of the reaction, solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography using petroleum ether (bp 60–80 °C) to afford the desired product 2a (116 mg, 0.96 mmol, mmol, 96percent) as a white solid,18 mp 132 °C. 1H NMR (CDCl3, 300 MHz) δ 5.08 (s, 1H), 7.11–7.12 (m, 2H), 7.25–7.36 (s, 7H), 7.42 (t, J = 7.29 Hz, 2H), 7.84 (d, J = 7.6 Hz, 2H) ppm.13C NMR (CDCl3,75 MHz) δ 54.4, 119.8, 125.3, 126.8, 127.3, 128.3, 128.7, 141.0, 141.6, 147.8 ppm.
84% With sulfuric acid In toluene at 20℃; for 2 h; To 130 g of a toluene solution of 9- (2-biphenyl) -9-fluorene alcohol obtained in Example 1,9.5 g (0.095 mol, 1.00 M.R.) of concentrated sulfuric acid was charged,The reaction was carried out at room temperature for 2 hours.After washing the resulting reaction mixture with caustic water,The organic layer containing the reaction mixture was washed with water until the washing water became neutral.After washing with water,After concentrating the organic layer to an appropriate place,255 g of methanol was added thereto for crystallization, followed by filtration and drying,24.0 g of white crystals of 9,9'-spirobifluorene (yield: 84percent, total yield from Example 1, purity 98percent) were obtained.
82% at 80℃; for 6 h; Under the protection of argon, 10 mmol of 9-fluorenone was added to the reaction flask.11mmol of 2-fluorobiphenyl and 20ml of tetrahydrofuran solvent, after stirring evenly,22 mmol of lithium metal tablets were added to the reaction solution in batches.Then, the temperature is raised to about 70 ° C, and the reaction is carried out for 6 hours. After the reaction is completed and returned to room temperature,The reaction was quenched with 20 mL of 1N aqueous hydrochloric acid. Dissolve to obtain an organic phase,The tetrahydrofuran was evaporated to dryness on a rotary evaporator to give a solid.The crude solid was added to 10 ml of acetic acid and heated to 80 ° C for 6 hours.After the completion of the ring closure reaction, the crude 9,9'-spirobifluorene was obtained by filtration.The crude product uses a mixed solvent of dichloromethane and n-hexane as an eluent.Perform column chromatography separation, and the chromatographic silica gel is 200-300 mesh.Finally, the product 9,9'-spirobifluorene 2.59g is obtained.The yield was 82percent.
Reference: [1] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
[2] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[3] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5662 - 5663
[4] European Journal of Organic Chemistry, 2010, # 21, p. 4004 - 4016
[5] Tetrahedron Letters, 2012, vol. 53, # 41, p. 5544 - 5547
[6] Journal of Organic Chemistry, 1984, vol. 49, p. 770 - 778
[7] Patent: JP6257340, 2018, B2, . Location in patent: Paragraph 0048; 0054
[8] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[9] Patent: CN108863694, 2018, A, . Location in patent: Paragraph 0033; 0034
[10] Journal of the American Chemical Society, 1930, vol. 52, p. 2881,2887
[11] Journal of the American Chemical Society, 1930, vol. 52, p. 2881,2887
[12] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[13] Synthetic Communications, 2008, vol. 38, # 12, p. 1888 - 1895
[14] Heterocycles, 2010, vol. 81, # 5, p. 1157 - 1168
[15] Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 907 - 916
[16] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 432 - 441
[17] Patent: KR2016/102949, 2016, A, . Location in patent: Paragraph 0074; 0076; 0077-0079
  • 3
  • [ 486-25-9 ]
  • [ 2052-07-5 ]
  • [ 159-66-0 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 4, p. 1663 - 1674
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[3] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
[4] Patent: EP1053578, 2002, B1,
[5] Tetrahedron Letters, 2012, vol. 53, # 41, p. 5544 - 5547
[6] Patent: JP6257340, 2018, B2,
  • 4
  • [ 486-25-9 ]
  • [ 2113-51-1 ]
  • [ 159-66-0 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 1, p. 145 - 158
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 3, p. 329 - 336
  • 5
  • [ 90-41-5 ]
  • [ 159-66-0 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 1, p. 145 - 158
[2] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5662 - 5663
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 3, p. 329 - 336
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 432 - 441
[5] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
  • 6
  • [ 2113-51-1 ]
  • [ 159-66-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[2] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5662 - 5663
[3] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 432 - 441
[4] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
  • 7
  • [ 86-73-7 ]
  • [ 1016-05-3 ]
  • [ 159-66-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 3, p. 384 - 387
  • 8
  • [ 14221-01-3 ]
  • [ 7440-44-0 ]
  • [ 159-66-0 ]
Reference: [1] Patent: US2012/32121, 2012, A1,
  • 9
  • [ 486-25-9 ]
  • [ 159-66-0 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[2] Journal of the American Chemical Society, 1930, vol. 52, p. 2881,2887
[3] Heterocycles, 2010, vol. 81, # 5, p. 1157 - 1168
[4] Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 907 - 916
[5] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[6] Patent: KR2016/102949, 2016, A,
  • 10
  • [ 2052-07-5 ]
  • [ 159-66-0 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[2] Heterocycles, 2010, vol. 81, # 5, p. 1157 - 1168
[3] Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 907 - 916
[4] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[5] Patent: KR2016/102949, 2016, A,
  • 11
  • [ 23533-35-9 ]
  • [ 159-66-0 ]
Reference: [1] Journal of the American Chemical Society, 1930, vol. 52, p. 2881,2887
  • 12
  • [ 67715-28-0 ]
  • [ 159-66-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 1473 - 1476
  • 13
  • [ 98-80-6 ]
  • [ 159-66-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[2] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
  • 14
  • [ 583-53-9 ]
  • [ 159-66-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[2] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
  • 15
  • [ 86-73-7 ]
  • [ 159-66-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[2] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
  • 16
  • [ 486-25-9 ]
  • [ 321-60-8 ]
  • [ 159-66-0 ]
Reference: [1] Patent: CN108863694, 2018, A,
  • 17
  • [ 159-66-0 ]
  • [ 128055-74-3 ]
YieldReaction ConditionsOperation in experiment
95% With FeCl3; bromine In dichloromethane d
2,2',7,7'-Tetrabromo-9,9'-spirobifluorene
80 mg (0.5 mmol) of anhydrous FeCl3 were added to a solution of 3.16 g (10.0 mmol) of 9,9'-spirobifluorene in 30 ml of methylene chloride, and 2.1 ml (41 mmol) of bromine in 5 ml of methylene chloride were added dropwise over a period of 10 minutes.
The solution was refluxed for 6 hours.
On cooling, the product precipitated.
The precipitate was filtered off with suction and washed with a little cold methylene chloride.
Drying gave 6.0 g (95percent) of the tetrabromo compound as a white solid.
100% With bromine; iron(III) chloride In chloroform 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene was prepared as follows.
To a solution of 9,9'-spirobifluorene (0.316 g 1.0 mmol) in chloroform (1.5 mL) at 0° C. was added ferric chloride (8 mg, 0.05 mol) and bromine (0.4 mL, 4.1 mmol).
The solution was warmed to room temperature and stirred for 3 h.
The resulting slurry that formed was poured into water and washed with saturated sodium thiosulfate until the red color disappeared.
The aqueous layer was extracted with methylene chloride (2*) and the combined organic layers were dried over magnesium sulfate to afford 0.63 g (100percent) of the title product as a white solid. IR 3051.6, 1594.7, 1570.8, 1450.1, 1396.2, 1249.3, 1059.7, 950.6 cm-1. 1 H NMR (300 MHz, CDCl3)δ 7.67 (d, J=8.4 Hz, 4H), 7.5 (dd, J=8.2, 1.8 Hz, 4H), 6.8 (d, J=1.5 Hz, 4H).
13 C NMR (75 MHz, CD2 Cl2)δ 149.3, 140.2. 132.1, 127.7, 122.4, 122.3, 65.7.
Calc'd for C25 H12 Br4: 631.7632. Found: 631.7630.
Calc'd for C25 H12 Br4: C, 47.51; H, 1.91. Found: C, 47.01; H, 1.97.
Reference: [1] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5662 - 5663
[2] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[3] Inorganic Chemistry, 2018, vol. 57, # 11, p. 6210 - 6213
[4] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
[5] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[6] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[7] Synthetic Communications, 2008, vol. 38, # 12, p. 1888 - 1895
[8] Journal of Organic Chemistry, 2012, vol. 77, # 4, p. 1663 - 1674
[9] Patent: US2003/111107, 2003, A1,
[10] Patent: US5026894, 1991, A,
[11] Patent: EP1053578, 2002, B1,
[12] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6334 - 6335
[13] Journal of Materials Chemistry C, 2013, vol. 1, # 11, p. 2183 - 2192
[14] Patent: CN106946750, 2017, A, . Location in patent: Paragraph 0125; 0126; 0127
[15] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2526 - 2536
  • 18
  • [ 159-66-0 ]
  • [ 171408-76-7 ]
Reference: [1] Chemistry Letters, 2008, vol. 37, # 8, p. 854 - 855
[2] Patent: JP6100258, 2017, B2, . Location in patent: Paragraph 0138; 0139
  • 19
  • [ 159-66-0 ]
  • [ 171408-84-7 ]
Reference: [1] Patent: CN106946750, 2017, A, . Location in patent: Paragraph 0107; 0108; 0109; 0120; 0121; 0123; 0124
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