Home Cart Sign in  
Chemical Structure| 78119-82-1 Chemical Structure| 78119-82-1

Structure of 78119-82-1

Chemical Structure| 78119-82-1

*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 [ 78119-82-1 ]

CAS No. :78119-82-1
Formula : C11H8O2
M.W : 172.18
SMILES Code : O=CC1=CC=C2C=C(O)C=CC2=C1
MDL No. :MFCD03427537
InChI Key :PRYNJOJHKYNLIS-UHFFFAOYSA-N
Pubchem ID :2764110

Safety of [ 78119-82-1 ]

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

Computational Chemistry of [ 78119-82-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 51.36
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.43
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

1.72
Log Po/w (WLOGP)?

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

2.36
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.

1.82
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

2.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.99

Water Solubility

Log S (ESOL):?

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

-2.49
Solubility 0.552 mg/ml ; 0.0032 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.

-2.12
Solubility 1.31 mg/ml ; 0.0076 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

-3.44
Solubility 0.0622 mg/ml ; 0.000361 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.

-6.13 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

1.0 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)

1.0

Application In Synthesis of [ 78119-82-1 ]

* 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 [ 78119-82-1 ]

[ 78119-82-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 78119-82-1 ]
  • [ 162709-84-4 ]
  • [ 1393356-57-4 ]
  • 2
  • [ 135908-33-7 ]
  • [ 78119-82-1 ]
  • [ 1544661-78-0 ]
YieldReaction ConditionsOperation in experiment
80% General procedure: Example 1: 4-(((6-(cyclohexyloxy)naphthalen-2-yl)methyl)amino) bicyclo[2.2.2]octane-l-carboxylic acid Step 1: 4-(((6-hvdroxynaphthalen-2-yl methyl amino bicvclor2.2.21octane-l-carboxylate 6-hydroxy-2-naphthaldehyde (520 mg, 3.02 mmol, 1.0 eq) and methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (663 mg, 3.62 mmol, 1.2 eq) were dissolved in toluene (100 mL). Magnesium sulfate (72 mg, 0.60 mmol, 0.2 eq) was added to the solution and refluxed for 48 h. The solvent was removed in vacuo. The residue was dissolved in THF (150 mL) and sodium cyanoborohydride (571 mg, 9.06 mmol, 3.0 eq) was added. The mixture was refluxed for 24 h. The solvent was removed in vacuo. Water (50 mL) was added to the residue and extracted with EtOAc (2x150 mL). The combined organic phase was washed with brine and dried over Na2S04. The organic phase was concentrated to give methyl 4-(((6-hydroxynaphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylate as yellow solid (819 mg, Y: 80%). ESI-MS (M+H)+: 340.2. 1H NMR (400 MHz, DMSO-d6) delta: 9.98 (s, 1H), 8.91 (br, 1H), 7.89 (s, 1H), 7.77 (d, / = 9.2 Hz, 1H), 7.75 (d, / = 8.4 Hz, 1H), 7.47 (dd, /= 8.4, 1.6 Hz, 1H), 7.15 (s, 1H), 7.14 (dd, /= 8.0, 2.4 Hz, 1H), 4.17 (s, 2H), 3.60 (s, 3H), 1.91-1.87 (m, 12H). Step 2: 4-(((6-(cvclohexyloxy naphthalen-2-yl methyl amino bicvclor2.2.21octane-l-carboxylic acid Methyl 4-(((6-hydroxynaphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylate (100 mg, 0.295 mmol, 1.0 eq), cyclohexyl methanesulfonate (100 mg, 0.885 mmol, 3.0 eq) and sodium hydroxide (35 mg, 0.875 mmol, 3.0 eq) were dissolved in DMF (2 mL). The mixture was stirred at 100 C for 2 h. After cooling to rt, 1 N HCl was added to adjust pH = 6-7 and extracted with DCM (2x40 mL). The organic phase was washed with brine and dried over Na2S04. After filtration and concentration, the residue was purified by prep-HPLC (65% MeOH/H20) to give 4-(((6-(cyclohexyloxy)naphthalen-2-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylic acid as a white solid (40 mg, yield: 33% in two steps). ESI-MS (M+H)+: 408.2. 1H NMR (400 MHz, CD3OD) delta: 7.89 (s, 1H), 7.84 (d, /= 8.4 Hz, 1H), 7.81 (d, /= 8.8 Hz, 1H), 7.49 (dd, /= 8.8, 2.0 Hz, 1H), 7.28 (d, / = 2.0 Hz, 1H), 7.20 (dd, / = 8.8, 2.4 Hz, 1H), 4.52-4.48 (m, 1H), 4.24 (s, 2H), 2.04-1.99 (m, 14H), 1.86-1.83 (m, 2H), 1.63-1.47 (m, 6H).
  • 3
  • [ 430-99-9 ]
  • [ 78119-82-1 ]
  • C14H9FO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.9 g With dmap; diisopropyl-carbodiimide; In dichloromethane; 7.0 g of a compound represented by the formula (I-5-8), 3.7 g of <strong>[430-99-9]2-fluoroacrylic acid</strong>, 0.1 g of N,N-dimethylaminopyridine, and 30 mL of dichloromethane were put into a reactor. 6.7 g of diisopropylcarbodiimide was dropwise added thereto and stirred. After ordinary post-treatment, this was purified through column chromatography and recrystallization to give 3.9 g of a compound represented by the formula (I-5-9).
  • 4
  • [ 78119-82-1 ]
  • [ 83883-26-5 ]
  • C27H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.4 g Under a nitrogen atmosphere,To the reaction vessel, 1.0 g of methanesulfonyl chloride,Tetrahydrofuran 5 mL,10 mg of 2,6-di-tert-butyl-4-methylphenol was added.It was cooled to -5 ° C.,A solution prepared by dissolving 2.0 g of the compound represented by the formula (D-2R-4) in 10 mL of tetrahydrofuran and 1.3 g of diisopropylethylamine were added dropwise, followed by stirring at -5 ° C. for 1 hour.9 mL of a tetrahydrofuran solution of 1.2 g of a compound represented by the formula (D-2 R-5)1.3 g of diisopropylethylamine,10 mg of 4-dimethylaminopyridine was added,And the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water and extracted with dichloromethane.Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane / methanol) gave 2.4 g of a compound represented by the formula (D-2 R-6).
  • 5
  • [ 78119-82-1 ]
  • [ 76350-90-8 ]
  • C25H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3 g 4 g of compound V and 4.2 g of compound IV, 8.4 g of triphenylphosphine (PPh3) were added to 40 ml of anhydrous tetrahydrofuran.After stirring for 15 minutes, 8.4 mL of diisopropyl azodicarboxylate (DIAD) was added dropwise in small portions to the reaction solution for 10 hours.After thin layer chromatography (TLC), the reaction mixture was poured into 100 mL of water and extracted with ethyl acetate (100 mL×5).The mixture was separated and washed with 5% sodium hydrogencarbonate (NaHCO3) (80 mL×3) and brine (80 mL×3), then dried over anhydrous magnesium sulfate. ester,Subsequent column chromatography V (petroleum ether): V (ethyl acetate)= 10:1 gave a yellow solid III 3g.
 

Historical Records

Technical Information

Categories