69605-90-9|[1,1'-Biphenyl]-3-ylmethanol| Ambeed

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Quality Control of [ 69605-90-9 ] Purity: 98% SDS Specification

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Product Details of [ 69605-90-9 ]

CAS No. :	69605-90-9
Formula :	C₁₃H₁₂O
M.W :	184.23
SMILES Code :	OCC1=CC(C2=CC=CC=C2)=CC=C1
MDL No. :	MFCD08703631
InChI Key :	WGUZZTGZDPJWSG-UHFFFAOYSA-N
Pubchem ID :	603556

Safety of [ 69605-90-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 69605-90-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	12
Fraction Csp3	0.08
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	58.01
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.34
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	3.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.69
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.	3.08
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	3.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.58
Solubility	0.0489 mg/ml ; 0.000265 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.	-3.42
Solubility	0.0699 mg/ml ; 0.000379 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	-4.74
Solubility	0.00332 mg/ml ; 0.000018 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	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.	-5.07 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	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<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)	1.57

Application In Synthesis of [ 69605-90-9 ]

* 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 [ 69605-90-9 ]

[ 69605-90-9 ] Synthesis Path-Downstream 1~35

1
[ 716-76-7 ]
[ 69605-90-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		Biphenyl-3-carboxylic acid (217.0 mg, 1.09 mmol) in THF was added to LiAlH4 (1.0 M in THF) (1.64 ml) at 00C under N2 during 15 min. The mixture was then stirred at r.t. for 2.5 h. H2O was carefully added to the mixture at 00C. NaOH (1.0 M) was added. The product was extracted wit EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding the title compound as a yellow oil (95%).1H NMR (CD3OD) delta 7.61-7.59 (m, 3H), 7.52-7.49 (m, IH), 7.45-7.38 (m, 3H), 7.35-7.30 (m, 2H), 4.67 (s, 2H).
95%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2.75h;Inert atmosphere;	Biphenyl-3-ylmethanol Biphenyl-3-carboxylic acid (217.0 mg, 1.09 mmol) in THF was added to LiAlH4 (1.0 M in THF) (1.64 ml) at 0 C. under N2 during 15 min. The mixture was then stirred at r.t. for 2.5 h. H2O was carefully added to the mixture at 0 C. NaOH (1.0 M) was added. The product was extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding the title compound as a yellow oil (95%). 1H NMR (CD3OD) delta 7.61-7.59 (m, 3H), 7.52-7.49 (m, 1H), 7.45-7.38 (m, 3H), 7.35-7.30 (m, 2H), 4.67 (s, 2H).
		EXAMPLE III STR20 To a suspension of 100 mg of lithium aluminum hydride in 20 mL of ether was added 500 mg 3-phenylbenzoic acid. The reaction mixture was stirred at room temperature overnight. After any excess lithium aluminum hydride was destroyed with water, the organic layer was washed successively with 25 mL aliquots of dilute hydrochloric acid, dilute sodium hydroxide and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure to yield 360 mg of 3-hydroxymethylbiphenyl as a crystalline solid.

References: [1]Patent: WO2010/97410,2010,A1 .Location in patent: Page/Page column 135.
[2]Patent: US2012/40942,2012,A1 .Location in patent: Page/Page column 63-64.
[3]Medicinal Chemistry Research,1996,vol. 6,p. 69 - 80.
[4]ChemMedChem,2015,vol. 10,p. 380 - 395.
[5]Bulletin of the Chemical Society of Japan,1959,vol. 32,p. 955,958.
[6]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7288 - 7300.
[7]Patent: US5594141,1997,A .

2
[ 2567-29-5 ]
[ 69605-90-9 ]

References: [1]Annales de Chimie (Cachan, France),1888,vol. <6> 15,p. 242.
Bulletin de la Societe Chimique de France,1888,vol. <2> 49,p. 98.

3
[ 2928-43-0 ]
[ 69605-90-9 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 7676 - 7684.
[2]Journal of the American Chemical Society,1989,vol. 111,p. 4887 - 4895.

4
[ 69605-90-9 ]
[ 1204-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With iodosylbenzene; In acetonitrile; at 60℃; for 2h;	General procedure: Oxidation of alcohols was typically carried out as follows: a suspension with 5 mg of the synthesized catalyst in acetonitrile (2 mL) was magnetically stirred, and the substrate namely alcohols (0.1 mmol) and PhIO (2.5 equiv.) was then added. The resulting mixture was kept at 60 C with magnetical stirring for a set time. The selectivity and conversion were determined by GC analysis.

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1204 - 1208.
[2]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7288 - 7300.
[3]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 4839 - 4853.
[4]Catalysis Communications,2015,vol. 65,p. 34 - 40.

5
[ 1016160-90-9 ]
[ 69605-90-9 ]

References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 4987 - 5000.

6
[ 103668-94-6 ]
[ 69605-90-9 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 3878 - 3881.

7
[ 82804-36-2 ]
[ 69605-90-9 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1204 - 1208.

8
[ 208941-39-3 ]
[ 98-80-6 ]
[ 69605-90-9 ]

References: [1]Synlett,1998,p. 671 - 675.

9
[ 69605-90-9 ]
[ 38580-82-4 ]

Yield	Reaction Conditions	Operation in experiment
	In thionyl chloride;	A solution of 50 mg of <strong>[69605-90-9]3-hydroxymethylbiphenyl</strong> in 1.5 mL thionyl chloride was heated at reflux temperature for 4 hr, cooled to room temperature and the solvent removed by evaporation under reduced pressure to yield 45 mg of 3-chloromethylbiphenyl which was used in the next step without further purification or characterization.

References: [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306.
[2]Medicinal Chemistry Research,1996,vol. 6,p. 69 - 80.
[3]Patent: US5594141,1997,A .
[4]Advanced synthesis and catalysis,2012,vol. 354,p. 2465 - 2472,8.
[5]Chemical Communications,2014,vol. 50,p. 11060 - 11062.

11
[ 69605-90-9 ]
[ 545-06-2 ]
2,2,2-trichloro-acetimidic acid biphenyl-3-ylmethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

12
[ 19926-50-2 ]
[ 69605-90-9 ]

References: [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306.

13
[ 69605-90-9 ]
C₆H₁₀N₂(CH₂C₆H₄C₆H₅)2 [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306.

14
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Amino-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

15
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Amino-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

16
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Azido-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587.

17
[ 69605-90-9 ]
N-benzyl-N-methyl-(3-phenyl)benzylamine [ No CAS ]