Home Cart Sign in  
Chemical Structure| 49826-70-2 Chemical Structure| 49826-70-2

Structure of 49826-70-2

Chemical Structure| 49826-70-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 49826-70-2 ]

CAS No. :49826-70-2
Formula : C12H11NO
M.W : 185.22
SMILES Code : C1(OCC2=CC=CC=C2)=CC=NC=C1
MDL No. :MFCD08235112
InChI Key :WBCDUONHBLSZED-UHFFFAOYSA-N
Pubchem ID :12328828

Safety of [ 49826-70-2 ]

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

Computational Chemistry of [ 49826-70-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.08
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 55.22
TPSA ?

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

22.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.14
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

2.32
Log Po/w (WLOGP)?

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

2.51
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.

1.75
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

2.88
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.32

Water Solubility

Log S (ESOL):?

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

-2.89
Solubility 0.241 mg/ml ; 0.0013 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.

-2.42
Solubility 0.699 mg/ml ; 0.00377 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

-4.69
Solubility 0.00381 mg/ml ; 0.0000206 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

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.

-5.78 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)

1.37

Application In Synthesis of [ 49826-70-2 ]

* 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 [ 49826-70-2 ]

[ 49826-70-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 7379-35-3 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃;
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5° C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5° C. for 10 min then warmed to 60° C. and stirred for 1.5 h. The mixture is then cooled to 23° C., treated with water, and extracted with EtOAc. The combined organics are dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
89%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 5℃; for 0.25 h;
Stage #2: at 5 - 60℃; for 1.75 h;
Example 3
Synthesis of 4-(benzyloxy)pyridine.
A flask is charged with NaH (60percent dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5 °C.
To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise.
The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min.
The resulting mixture is stirred at 5 °C for 10 min then warmed to 60 °C and stirred for 1.5 h.
The mixture is then cooled to 23 °C, treated with water, and extracted with EtOAc.
The combined organics are dried with MgSO4, filtered, and concentrated in vacuo.
Purification of the crude by flash chromatography (SiO2, 5percent EtOAc in hexanes to 50percent EtOAc in hexanes) gives the title intermediate (1.10 g, 89percent).
References: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767.
[2] Patent: US2011/275627, 2011, A1, . Location in patent: Page/Page column 60.
[3] Patent: EP2331541, 2011, A1, . Location in patent: Paragraph 0070; 0071.
  • 2
  • [ 2683-66-1 ]
  • [ 49826-70-2 ]
References: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 10, p. 1752 - 1757.
[2] Synlett, 2005, # 9, p. 1389 - 1392.
[3] Journal of Organic Chemistry, 1959, vol. 24, p. 330,332.
[4] Chemical and Pharmaceutical Bulletin, 1959, vol. 7, p. 149.
  • 3
  • [ 626-61-9 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
References: [1] Tetrahedron, 1987, vol. 43, # 11, p. 2557 - 2564.
[2] Patent: WO2010/90716, 2010, A1, . Location in patent: Page/Page column 301.
  • 4
  • [ 626-64-2 ]
  • [ 100-39-0 ]
  • [ 49826-70-2 ]
YieldReaction ConditionsOperation in experiment
82% at 80℃; for 2 h; Green chemistry General procedure: Phenol (0.5 mmol), benzyl bromide(1.2 mmol) and KOH (2.0 mmol) was added to the DES (1 mL) and heated at temperature (80°C) for 2 h. After cooling to room temperature water was added and the product was extracted with ethyl acetate (1 3 mL) andanalyzed by GC–MS after the addition of hexamethylbenzene as an internal standard. The product was purified using column chromatography on silica gel(hexane/EtOAc::99:1). The pure product was characterized by 1H NMR and 13CNMR.Table 4 Comparison of different methodologies for benzylation of phenols with benzyl bromide
References: [1] Tetrahedron Letters, 2014, vol. 55, # 52, p. 7243 - 7246.
  • 5
  • [ 15854-87-2 ]
  • [ 100-51-6 ]
  • [ 49826-70-2 ]
References: [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935.
  • 6
  • [ 626-64-2 ]
  • [ 100-44-7 ]
  • [ 49826-70-2 ]
References: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 8, p. 800 - 802.
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 8, p. 800 - 802.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 49826-70-2 ]

Aryls

Chemical Structure| 85333-26-2

A517002 [85333-26-2]

2-Amino-4-benzyloxypyridine

Similarity: 0.84

Chemical Structure| 1253792-64-1

A140752 [1253792-64-1]

4-(Benzyloxy)-2-fluoropyridine

Similarity: 0.82

Chemical Structure| 4783-86-2

A323907 [4783-86-2]

4-Phenoxypyridine

Similarity: 0.80

Chemical Structure| 96166-00-6

A132697 [96166-00-6]

5-(Benzyloxy)pyridin-2-amine

Similarity: 0.77

Chemical Structure| 725256-57-5

A153122 [725256-57-5]

6-(Benzyloxy)pyridin-3-ol

Similarity: 0.75

Ethers

Chemical Structure| 85333-26-2

A517002 [85333-26-2]

2-Amino-4-benzyloxypyridine

Similarity: 0.84

Chemical Structure| 1253792-64-1

A140752 [1253792-64-1]

4-(Benzyloxy)-2-fluoropyridine

Similarity: 0.82

Chemical Structure| 1418117-87-9

A482939 [1418117-87-9]

5-Methoxyisoquinoline hydrochloride

Similarity: 0.81

Chemical Structure| 4783-86-2

A323907 [4783-86-2]

4-Phenoxypyridine

Similarity: 0.80

Chemical Structure| 1220021-59-9

A235305 [1220021-59-9]

4-Ethoxynicotinaldehyde

Similarity: 0.78

Related Parent Nucleus of
[ 49826-70-2 ]

Pyridines

Chemical Structure| 85333-26-2

A517002 [85333-26-2]

2-Amino-4-benzyloxypyridine

Similarity: 0.84

Chemical Structure| 1253792-64-1

A140752 [1253792-64-1]

4-(Benzyloxy)-2-fluoropyridine

Similarity: 0.82

Chemical Structure| 4783-86-2

A323907 [4783-86-2]

4-Phenoxypyridine

Similarity: 0.80

Chemical Structure| 1220021-59-9

A235305 [1220021-59-9]

4-Ethoxynicotinaldehyde

Similarity: 0.78

Chemical Structure| 96166-00-6

A132697 [96166-00-6]

5-(Benzyloxy)pyridin-2-amine

Similarity: 0.77