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Structure of 67665-47-8

Chemical Structure| 67665-47-8

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Product Details of [ 67665-47-8 ]

CAS No. :67665-47-8
Formula : C25H14Br2
M.W : 474.19
SMILES Code : BrC1=CC(C23C4=C(C5=C2C=CC=C5)C=CC(Br)=C4)=C(C6=C3C=CC=C6)C=C1
MDL No. :MFCD08704219
InChI Key :OZZSXAWYZYTWQD-UHFFFAOYSA-N
Pubchem ID :11282885

Safety of [ 67665-47-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 67665-47-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 27
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 118.14
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.22
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

7.76
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

7.56
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

7.23
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

7.89
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.93

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-8.33
Solubility 0.00000224 mg/ml ; 0.0000000047 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-7.6
Solubility 0.0000118 mg/ml ; 0.0000000249 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-11.76
Solubility 0.0000000008 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-3.68 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.75

Application In Synthesis of [ 67665-47-8 ]

* 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.

  • Downstream synthetic route of [ 67665-47-8 ]

[ 67665-47-8 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 188290-36-0 ]
  • [ 67665-47-8 ]
  • 2,2'-bis(2-thienyl)-9,9'-spirobifluorene [ No CAS ]
  • 3
  • [ 1081-34-1 ]
  • [ 67665-47-8 ]
  • 2,2'-bis(2,2':5',2''-terthiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]
  • 4
  • [ 67665-47-8 ]
  • 4-hexyl-2-thienylzinc chloride [ No CAS ]
  • [ 445498-72-6 ]
  • 5
  • [ 67665-47-8 ]
  • C20H29ClS2Zn [ No CAS ]
  • [ 445498-74-8 ]
  • 6
  • [ 67665-47-8 ]
  • sodium 4-hexyl-2-thienyl trihydroxyboranuide [ No CAS ]
  • [ 445498-72-6 ]
  • 7
  • [ 67665-47-8 ]
  • C30H43ClS3Zn [ No CAS ]
  • C85H100S6 [ No CAS ]
  • 9
  • [ 67665-47-8 ]
  • [ 492-97-7 ]
  • 2,2'-bis(2,2'-bithiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]
  • 10
  • [ 67665-45-6 ]
  • [ 67665-47-8 ]
  • 11
  • [ 108-86-1 ]
  • [ 67665-47-8 ]
  • [ 196207-58-6 ]
  • [ 98-80-6 ]
  • poly(9,9-dioctylfluorene)-alt-co-(9,9\-spirobifluorene), Mn = 14000, Mw/Mn = 1.5; monomer(s): 2,2\-dibromo-9,9\-spirobifluorene; 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene; phenylboronic acid; bromobenzene [ No CAS ]
  • 12
  • [ 67665-47-8 ]
  • [ 67665-45-6 ]
  • 14
  • [ 67665-47-8 ]
  • [ 4885-02-3 ]
  • [ 864957-75-5 ]
  • 15
  • [ 67665-47-8 ]
  • [ 122-39-4 ]
  • 2,2’-bis(N,N-diphenylamine)-9,9'-spirobifluorene [ No CAS ]
  • 16
  • [ 67665-47-8 ]
  • [ 207742-45-8 ]
  • [ 250597-29-6 ]
  • poly[fluorenedithieno[3,2-b:2,,3-d]silole-alt 2,2-spirobifluorelene]; molar ratios of DTS, SBF and fluorene were 1:4:5 [ No CAS ]
  • 17
  • [ 67665-47-8 ]
  • [ 207742-45-8 ]
  • [ 250597-29-6 ]
  • poly[fluorenedithieno[3,2-b:2,,3-d]silole-alt 2,2-spirobifluorelene]; molar ratios of DTS, SBF and fluorene were 2:3:5 [ No CAS ]
  • 18
  • [ 912562-10-8 ]
  • [ 67665-47-8 ]
  • [ 250597-29-6 ]
  • poly[fluorenedithieno[3,2-b:2,,3-d]phosphole oxide-alt-2,2-spirobifluorelene]; molar ratios of DTPO, SBF and fluorene were 1:4:5 [ No CAS ]
  • 19
  • [ 912562-10-8 ]
  • [ 67665-47-8 ]
  • [ 250597-29-6 ]
  • poly[fluorenedithieno[3,2-b:2,,3-d]phosphole oxide-alt-2,2-spirobifluorelene]; molar ratios of DTPO, SBF and fluorene were 2:3:5 [ No CAS ]
  • 22
  • [ 67665-47-8 ]
  • [ 790674-48-5 ]
  • 25
  • [ 67665-44-5 ]
  • [ 67665-47-8 ]
  • 30
  • [ 67665-47-8 ]
  • C44H35N3O8 [ No CAS ]
  • C113H82N6O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.2% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 105 - 110℃; for 5h;Inert atmosphere; 250mL Three-necked flask was added 1.04g (2.2 × 10-3mol) 2,2'- dibromo spirofluorene, 3.21g (4.4 × 10-3mol) intermediate 9 (prepared by Example a), 0.64g (6.6 × 10 -3mol) sodium tert-butoxide and 50.0g of toluene, was added 0.06g (6.6 × 10-5mol) under nitrogen Pd2 (dba) 3,0.025g (1.32 × 10-4mol) (t-Bu) 3PH · BF4, heating to 105 ~ 110 reaction 5h. The reaction was completed, the reaction solution was filtered, and the filtrate washed with water 50g × 2. The organic phase was dried over anhydrous sodium sulfate, and columned on silica gel, toluene off under reduced pressure. Recrystallized from ethanol to give pale yellow powdery solid 2.86g, yield 73.2percent.
  • 31
  • [ 67665-47-8 ]
  • [ 73183-34-3 ]
  • [ 676168-63-1 ]
YieldReaction ConditionsOperation in experiment
27.6% With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 70℃; for 18h;Inert atmosphere; Compound A (2.00 g, 4.22 mmol), bis (pinacolato) diboron (2.36 g, 9.30 mmol), [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) ([1,1'-Bis (diphenylphosphino) ferrocene] dichloropalladium (II), Pd (dppf) Cl2) (0.31g, 0.42mmol), 1,1'-bis (diphenylphosphino) ferrocene (1 Flask of 70 mL of 1'-bis (diphenylphosphino) ferrocene, dppf) (0.234 g, 0.42 mmol), potassium acetate (KOAc) (2.55 g, 26 mmol) and 1,4-dioxane (1,4-dioxaen) Was charged with nitrogen and reacted at 70 C. for 18 hours. After cooling to room temperature, the product was extracted with methylene chloride (MC) and washed well with water. The extracted organics were dried over anhydrous magnesium sulfate (anhydrous MgSO 4). Then, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1 (eluent)) to obtain 1.58 g of compound A-1. (Yield 27.6%) GC-MS: 568.22 is a diagram showing an MS measurement result of Compound A-1.
  • 32
  • [ 67665-47-8 ]
  • ((2,2'-bis(diphenylamino)-9,9'-spirobi[fluorene]-7,7'-diyl)bis(methanylylidene))bis(3-ethyl-2-thioxothiazolidin-4-one) [ No CAS ]
  • 33
  • [ 67665-47-8 ]
  • 2,2'-((2,2'-bis(diphenylamino)-9,9'-spirobi[fluorene]-7,7'-diyl)bis(methanylylidene))dimalononitrile [ No CAS ]
  • 34
  • [ 67665-47-8 ]
  • [ 861317-95-5 ]
  • C61H38N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.2% With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; at 100℃; for 20h;Inert atmosphere; Schlenk technique; 100 mL with argon substitution, equipped with a stirrerTo a Schlenk tube of N-phenyldibenzo [b, d] furan-4-amine (1.15 g, 4.43 mmol), <strong>[67665-47-8]2,2'-dibromo-9,9'-spirobifluorene</strong> (1.00 g, 11 mmol), palladium acetate (40 mg, 0.18 mmol), toluene (40 mL)Tri-t-butylphosphine (36 mg, 0.18 mmol) and potassium t-butoxide (1.0 g, 8.9 mmol) were placed and sealed, followed by stirring at 100 ° C. for 20 hours.Thereafter, the reaction vessel was allowed to cool to near room temperature, the lid was opened, and water (30 mL) was added thereto. The content was transferred to a separating funnel, the organic layer and the aqueous layer were separated, the aqueous layer was removed, and the organic layer was washed with water.The organic layer was dried over sodium sulfate. Thereafter, sodium sulfate was removed by filtration, and the organic layer was concentrated.The concentrated mixture was purified by silica gel column chromatography (developing solvent: hexane / dichloromethane = 3/1) to obtain the objective compound represented by the above chemical formula (31) (yield 1.51 g, yield Rate 86.2percent).
  • 35
  • [ 67665-47-8 ]
  • [ 1252914-52-5 ]
  • C61H38N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; at 100℃; for 20h;Schlenk technique; Inert atmosphere; Sealed tube; A stirrer,N-phenyldibenzo [b, d] thiophene-4-amine (0.55 g, 2.0 mmol) was added to a 100 mL Schlenk flask purged with argon,<strong>[67665-47-8]2,2'-dibromo-9,9'-spirobifluorene</strong> (0.47 g, 1.0 mmol),Palladium acetate (9.0 mg, 0.04 mmol),Toluene (40 mL), tri-t-butylphosphine (8.1 mg,0.04 mmol) and potassium t-butoxide (0.22 g, 2.0 mmol) were put in a reaction vessel and sealed,And the mixture was stirred at 100 ° C. for 20 hours. Thereafter, the reaction vessel was allowed to cool to near room temperature,Open the lid and put water (30 mL) into it. Transfer contents to a separating funnel,After separating the organic phase and aqueous phase, the aqueous phase was removed and the organic phase was washed with water.The organic phase was dried over sodium sulfate. after that,The sodium sulfate was removed by filtration and the organic phase was concentrated.The concentrated mixture was purified by silica gel column chromatography (developing solvent: hexane / dichloromethane = 3/1)To obtain a target compound represented by the above general formula (6)(Yield 0.38 g, yield 44.0percent).
 

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