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Structure of 83802-71-5

Chemical Structure| 83802-71-5

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Product Details of [ 83802-71-5 ]

CAS No. :83802-71-5
Formula : C10H9FO2
M.W : 180.18
SMILES Code : O=C1CCC2=C1C=C(OC)C(F)=C2
MDL No. :MFCD09261202
InChI Key :FFZRFPIFJVKURP-UHFFFAOYSA-N
Pubchem ID :13059023

Safety of [ 83802-71-5 ]

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

Computational Chemistry of [ 83802-71-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 45.94
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.03
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

1.74
Log Po/w (WLOGP)?

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

2.38
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.

1.76
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

3.14
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.21

Water Solubility

Log S (ESOL):?

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

-2.33
Solubility 0.845 mg/ml ; 0.00469 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-1.91
Solubility 2.22 mg/ml ; 0.0123 mol/l
Class?

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

Very 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

-3.52
Solubility 0.0542 mg/ml ; 0.000301 mol/l
Class?

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

Soluble

Pharmacokinetics

GI absorption?

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

High
BBB permeant?

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

Yes
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

No
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

No
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.

-6.16 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

0.0
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

0.0
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

1.0
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<1.0
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)

1.86

Application In Synthesis of [ 83802-71-5 ]

* 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.

  • Downstream synthetic route of [ 83802-71-5 ]

[ 83802-71-5 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 83802-71-5 ]
  • [ 83802-72-6 ]
  • 2
  • [ 83802-70-4 ]
  • [ 83802-71-5 ]
  • 3
  • phenylmagnesium bromide [ No CAS ]
  • [ 83802-71-5 ]
  • 5-fluoro-6-methoxy-1-phenyl-1H-indene [ No CAS ]
  • 4
  • [ 83802-71-5 ]
  • trans-2-amino-5-fluoro-6-methoxy-1-phenyl-2,3-dihydro-1H-indene [ No CAS ]
  • 5
  • [ 83802-71-5 ]
  • [ 83802-73-7 ]
  • 6
  • [ 83802-71-5 ]
  • [ 78114-96-2 ]
  • 7
  • [ 83802-71-5 ]
  • [ 344313-40-2 ]
  • 8
  • [ 83802-71-5 ]
  • 6-fluoro-5-<3-(4-phenyl-1-piperazinyl)propoxy>indan [ No CAS ]
  • 9
  • [ 83802-71-5 ]
  • 6-fluoro-5-[4-(4-phenyl-1-piperazinyl)butoxy]indane [ No CAS ]
  • 10
  • [ 83802-71-5 ]
  • 6-fluoro-5-{3-[4-(3-chlorophenyl)-1-piperazinyl]propoxy}indane [ No CAS ]
  • 11
  • [ 83802-71-5 ]
  • 6-fluoro-5-{3-[4-(4-fluorophenyl)-1-piperazinyl]propoxy}indane [ No CAS ]
  • 12
  • [ 83802-71-5 ]
  • 6-fluoro-5-{4-[4-(4-fluorophenyl)-1-piperazinyl]butoxy}indane [ No CAS ]
  • 13
  • [ 83802-71-5 ]
  • 6-fluoro-5-{3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propoxy}indane [ No CAS ]
  • 14
  • [ 69888-90-0 ]
  • [ 83802-71-5 ]
YieldReaction ConditionsOperation in experiment
91% Reference Example 9 5-Fluoro-6-methoxy-1-indanone In the same manner as in Reference Example 6, the target compound was obtained from 3-(3-fluoro-4-methoxyphenyl)propionic acid. The yield was 91percent. m.p.: 152-153° C. (recrystallized from methanol/ethyl acetate); NMR (CDCl3) delta: 2.71 (2H, t, J=5.7 Hz), 3.08 (2H, t, J=5.7 Hz), 3.92 (3H, s), 7.17 (1H, d, J=10.3 Hz), 7.29 (d, J=8.1 Hz); Elemental Analysis for C10 H9 FO2: Calcd.: C 66.66; H 5.03; Found: C 66.82; H 5.06
A mixture of Compound II (900 mg), toluene (9 mL) and thionyl chloride (393 muL) was stirred at 90° C. for one hour, and concentrated under reduced pressure. The obtained residue was added to an ice-cold solution of aluminium chloride (605 mg) in methylene chloride (45 mL), and the mixture was stirred for one hour. The reaction solution was added dropwise into ice-cold water, and the mixture was stirred for one hour, ane extracted with ether. The organic layer was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give Compound III (666 mg).
  • 15
  • [ 2537-48-6 ]
  • [ 83802-71-5 ]
  • [ 187872-53-3 ]
YieldReaction ConditionsOperation in experiment
75% Reference Example 10 (E)-(5-fluoro-6-methoxyindan-1-ylidene) acetonitrile In the same manner as in Reference Example 7, the target compound was obtained from <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> and diethyl cyanomethylphosphonate. The yield was 75percent. m.p.: 197-199° C. (recrystallized from hexane/ethyl acetate); NMR (CDCl3) delta: 3.00-3.19 (4H, m), 3.92 (3H, s), 5.53 (1H, t, J=2.2 Hz), 7.02 (1H, d, J=7.6 Hz), 7.07 (1H, d, J=10.3 Hz); Elemental Analysis for C12 H10 FNO: Calcd.: C 70.93; H 4.96; N 6.89; Found: C 70.65; H 5.13; N 6.99
  • 16
  • [ 1120-87-2 ]
  • [ 83802-71-5 ]
  • [ 788801-93-4 ]
YieldReaction ConditionsOperation in experiment
Example 4 4-(6-fluoro-indan-1-yl)piperidine This compound was prepared in two steps from 4-bromopyridine and <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> as described in method 2 above to give the product as the HCl salt (66percent, mp: 178°-179° C.). Anal. Calc'd for C15 H2 FNOodsold;HCl: C, 63.04percent; H, 7.41percent; N, 4.90percent. Found: C, 62.80percent; H, 7.30percent; N, 4.70percent.
  • 17
  • [ 351-54-2 ]
  • [ 83802-71-5 ]
YieldReaction ConditionsOperation in experiment
Example 7 1-(5-fluoro-6-methoxy-indan-1-yl)piperazine 3-Fluoro-4-methoxybenzaldehyde was converted to 5-fluoro-6-methoxy-1-indanone by method 2, steps 1-4 above, (92percent, mp 149°-151° C.). Anal. Calc'd for C10 H9 FO2: C, 66.66percent; H, 5.03percent. Found: C, 66.65percent; H, 4.96percent.
  • 18
  • [ 7755-92-2 ]
  • [ 83802-71-5 ]
  • [ 185678-63-1 ]
YieldReaction ConditionsOperation in experiment
88% With sodium borohydrid;titanium(IV) isopropylate; 1-Formyl-piperazine (2.1 g, 20 mmol), 5-fluoro-6-methoxy-indan-1-one (1.8 g, 10 mmol), titanium(IV) isopropoxide (5 ml, 15 mmol), and sodium borohydride (1.2 g, 30 mmol) were reacted by Method B to give the product (2.2 g, 88percent, mp 163°-166° C.). Calcd for C14 H19 FN2 O.C4 H4 O4.0.1H2 O: C, 56.23percent; H, 6.56percent; N, 7.28percent. Found: C, 56.65percent; H, 6.41percent; N, 6.98percent.
  • 19
  • [ 69888-90-0 ]
  • [ 187872-11-3 ]
  • [ 83802-71-5 ]
YieldReaction ConditionsOperation in experiment
94% Reference Example 23 5-Fluoro-6-methoxy-1-indanone Starting with 3-(3-fluoro-4-methoxyphenyl)propionic acid, the title compound was synthesised in otherwise the same manner as Reference Example 11 (yield 94percent). m.p. 152-154° C. NMR(CDCl3) delta: 2.70(2H,t,J=5.5 Hz), 3.07(2H,t,J=5.5 Hz), 3.91(3H,s), 7.17(1H,d,J=10.3 Hz), 7.29(1H,d,J=10.3 Hz). Elemental analysis for C10 H9 FO2: Calcd.: C, 66.66; H, 5.03. Found: C, 66.85; H, 4.97.
  • 20
  • [ 83802-71-5 ]
  • [ 187872-53-3 ]
  • [ 187871-98-3 ]
YieldReaction ConditionsOperation in experiment
73% Reference Example 24 (E)-(5-Fluoro-6-methoxyindan-1-ylidene)acetonitrile Starting with <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> and diethyl cyanomethylphosphate, the title compound was synthesised in otherwise the same manner as Reference Example 8 (yield 73percent). m.p. 197-199° C. NMR(CDCl3) delta: 3.00-3.19(4H,m), 3.91(3H,s), 5.52(1H,br s), 6.99-7.10(2H,m).
  • 21
  • [ 2537-48-6 ]
  • [ 83802-71-5 ]
  • (E)-(5-fluoro-6-methoxyindan-1-ylidene)acetonitrile [ No CAS ]
  • 22
  • [ 83802-71-5 ]
  • [ 917885-01-9 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide; In dichloromethane; at 20℃; for 7h;Cooling with ice; To an ice-cold solution of Compound III (666 mg) in methylene chloride (15 mL) was added dropwise boron tribromide (4.44 mL), and the mixture was stirred at room temperature for 7 hours. The reaction solution was cooled with ice, and thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to give Compound III (52 mg).
  • 23
  • [ 83802-71-5 ]
  • [ 1307255-50-0 ]
 

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