101349-12-6|2-(5-Fluoro-1H-indol-3-yl)ethanol| Ambeed

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Quality Control of [ 101349-12-6 ] Purity: 98% SDS Specification

COA

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Product Details of [ 101349-12-6 ]

CAS No. :	101349-12-6
Formula :	C₁₀H₁₀FNO
M.W :	179.19
SMILES Code :	FC1=CC2=C(NC=C2CCO)C=C1
MDL No. :	MFCD09752697
InChI Key :	MXTYSYXDDDVPBQ-UHFFFAOYSA-N
Pubchem ID :	13616248

Safety of [ 101349-12-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 101349-12-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.2
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	49.19
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.69
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.2
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.26
Log P_o/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.	1.68
Log P_o/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	3.09
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.72
Solubility	0.344 mg/ml ; 0.00192 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.	-2.59
Solubility	0.46 mg/ml ; 0.00257 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.79
Solubility	0.0287 mg/ml ; 0.00016 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.	-5.83 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)	1.65

Application In Synthesis of [ 101349-12-6 ]

* 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.

Downstream synthetic route of [ 101349-12-6 ]

[ 101349-12-6 ] Synthesis Path-Downstream 1~35

1
[ 4949-44-4 ]
[ 101349-12-6 ]
[ 57816-80-5 ]

References: [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 391 - 395.

2
[ 18162-48-6 ]
[ 101349-12-6 ]
[ 101349-34-2 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1704 - 1712.
[2]Organic Letters,2006,vol. 8,p. 4397 - 4400.
[3]Organic Letters,2014,vol. 16,p. 1908 - 1911.

3
[ 582320-41-0 ]
[ 101349-12-6 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1704 - 1712.

4
[ 443-73-2 ]
[ 101349-12-6 ]

Yield	Reaction Conditions	Operation in experiment
100%		To a solution of 5-fluoroindole -3-acetic acid (ig, 5.2mmol) in THE (2Oml) was added a1M solution of lithium aluminium hydride in THE (10.4m1, 10.4mmol) and the mixturerefluxed for 1.5 hours. The mixture was cooled, 0.39m1 of water and then 0.39m1 of15% NaOH(aq) added, followed by I .2m1 of water. The precipitate was collected viavacuum filtration and the filtrate concentrated to give 2-(5-fluoro-1 H-indol-3-yl)ethanol,an orange oil (0.927g, 100%); ?H NMR (400 MHz, CHLOROEORM-d) 6 ppm 2.98 (t,J=6.41 Hz, 2 H)1 3.89 (t, J=6.18 Hz, 2 H), 6.95 (td, J9.04, 2.52 Hz, I H), 7.12 (s, 1 H), 7.22 - 7.30 (m, 2 H), 8.06 (br. S., 1 H).

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.
[2]Patent: WO2017/85484,2017,A1 .Location in patent: Page/Page column 76; 77.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 1402 - 1406.
Angew. Chem.,2016,vol. 129,p. 1423 - 1427,5.
[4]Organic Letters,2006,vol. 8,p. 4397 - 4400.
[5]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.

5
[ 101349-12-6 ]
[ 127561-10-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 5h;	To a solution of <strong>[101349-12-6]2-(5-fluoro-1H-indol-3-yl)ethanol</strong> (18a) (10g,55.8 mmol) in CH2Cl2 (200 mL) was added successively CBr4 (27.76 g, 83.71 mmol) and PPh3 (21.52 g, 82.03 mmol) at 0 C. Themixture was stirred at room temperature for 5 h. After thecompletion of reaction, the solvent was concentrated underreduced pressure. The residue was purified by column chromatographyon silica gel (PE/EA = 5:1, V/V) to give compound 19a as ayellow oil (9.46 g, 70%) [27]. MS (ESI) m/z: 242.06 [M+H]+.
70%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 5h;	To a solution of <strong>[101349-12-6]2-(5-fluoro-1H-indol-3-yl)ethanol</strong> (3a) (10 g, 55.8 mmol) in CH2Cl2 (200 mL) was added successively CBr4 (27.76 g, 83.71 mmol) and PPh3 (21.52 g, 82.03 mmol) at 0 oC. The mixture was stirred at room temperature for 5h. After the completion of reaction, the solvent was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EA= 5:1, V/V) to give compound 4a as a yellow oil (9.46 g, 70%) . MS (ESI) m/z: 242.06 [M+H]+.

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.
[2]European Journal of Medicinal Chemistry,2018,vol. 144,p. 701 - 715.
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29.
[4]Journal of Organic Chemistry,2015,vol. 80,p. 2062 - 2071.
[5]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1159 - 1163.
[6]Archiv der Pharmazie,2014,vol. 347,p. 32 - 41.

6
[ 98-59-9 ]
[ 101349-12-6 ]
[ 1027596-82-2 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 1402 - 1406.
Angew. Chem.,2016,vol. 129,p. 1423 - 1427,5.

7
[ 497258-29-4 ]
[ 101349-12-6 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.

8
[ 101349-12-6 ]
2-(3"-(5"-fluoro-indolyl)ethyloxy)adenosine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.

9
[ 101349-12-6 ]
[ 936252-55-0 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 1402 - 1406.
Angew. Chem.,2016,vol. 129,p. 1423 - 1427,5.

10
[ 101349-12-6 ]
[ 936252-76-5 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.

11
[ 101349-12-6 ]
[ 936252-92-5 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1810 - 1827.

12
[ 101349-12-6 ]
[ 913941-83-0 ]

References: [1]Organic Letters,2006,vol. 8,p. 4397 - 4400.
[2]Organic Letters,2014,vol. 16,p. 1908 - 1911.

13
[ 101349-12-6 ]
[ 913941-84-1 ]