Home Cart Sign in  
Chemical Structure| 491-37-2 Chemical Structure| 491-37-2

Structure of 491-37-2

Chemical Structure| 491-37-2

*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 [ 491-37-2 ]

CAS No. :491-37-2
Formula : C9H8O2
M.W : 148.16
SMILES Code : O=C1CCOC2=C1C=CC=C2
MDL No. :MFCD00006840
InChI Key :MSTDXOZUKAQDRL-UHFFFAOYSA-N
Pubchem ID :68110

Safety of [ 491-37-2 ]

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

Computational Chemistry of [ 491-37-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 41.01
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.

1.76
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

1.38
Log Po/w (WLOGP)?

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

1.65
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.

1.05
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

2.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.66

Water Solubility

Log S (ESOL):?

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

-2.03
Solubility 1.38 mg/ml ; 0.0093 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.

-1.54
Solubility 4.32 mg/ml ; 0.0291 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

-2.84
Solubility 0.216 mg/ml ; 0.00146 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.

-6.22 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)

1.81

Application In Synthesis of [ 491-37-2 ]

* 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.

  • Downstream synthetic route of [ 491-37-2 ]

[ 491-37-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 491-37-2 ]
  • [ 7677-24-9 ]
  • [ 20426-80-6 ]
  • 2
  • [ 122-97-4 ]
  • [ 254-04-6 ]
  • [ 254-03-5 ]
  • [ 493-08-3 ]
  • [ 491-37-2 ]
  • [ 19090-04-1 ]
  • [ 100-52-7 ]
  • 3
  • [ 122-97-4 ]
  • [ 254-03-5 ]
  • [ 493-08-3 ]
  • [ 491-37-2 ]
  • [ 19090-04-1 ]
  • 4
  • [ 491-37-2 ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
Preparation Example 7 By the reaction and treatment in the same manner as in Preparation Example 5 using 4-chromanone (5.1 g) as a starting material, chroman-4-carboxylic acid (4.1 g) was obtained. melting point: 94.3ØC
  • 6
  • [ 491-37-2 ]
  • [ 38222-83-2 ]
  • [ 461666-59-1 ]
YieldReaction ConditionsOperation in experiment
94% With trifluoromethanesulfonic acid anhydride; In hexane; dichloromethane; (34a) Trifluoromethanesulfonic anhydride (1.2 mL, 7.4 mmol)was added drop wise to a stirring solution of chroman-4-one (1.0 g, 6.7 mmol), 2,6-di-t-butyl-4-methyl pyridine (1.59 g, 7.7 mmol) in dichloromethane (40 mL), under nitrogen atmosphere. The reaction was heated to reflux for 2 h, allowed to cool to room temperature and was concentrated in vacuo to give a semi solid residue. This was treated with hexane and the solids were filtered off. The filtrate was concentrated to give 4-[(trifluoromethyl)sulfonyl]-2H-chromene (1.78 g, 94percent) as an orange oil.
  • 7
  • [ 80-65-9 ]
  • [ 491-37-2 ]
  • [ 7732-18-5 ]
  • [ 67863-81-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; isopropyl alcohol; EXAMPLE I 3-[(4-Chromanylidene)amino]-2-oxazolidinone A 62-g (0.61 mole) portion of <strong>[80-65-9]3-amino-2-oxazolidinone</strong> was charged in a 500-ml, 3-necked flask equipped with a thermometer, stirrer and reflux condenser, and treated successively with 92 ml of H2 O, 8 ml of 10% HCl and 42 g (0.28 mole) of 4-chromanone in 200 ml ethanol. The reaction mixture was refluxed for 36 hr, stripped in vacuo to one-half volume and cooled in the refrigerator overnight. The slurry was filtered and the white crystalline solid washed with 50 ml of isopropanol then 200 ml of ether and dried. M.p. 105-108. Yield: 44 g (68%). The filtrate was extracted with 250 ml of CHCl3, and the CHCl3 extract dried over MgSO4, filtered, and stripped in vacuo.
With hydrogenchloride; In ethanol; isopropyl alcohol; A. 3-[(4-Chromanylidene)amino]-2-oxazolidinone A 62 g (0.61 mole) portion of <strong>[80-65-9]3-amino-2-oxazolidinone</strong> was charged in a 500 ml, 3-necked flask equipped with a thermometer, stirrer and reflux condenser, and treated successively with 92 ml of H2 O, 8 ml of 10% HCl and 42 g (0.28 mole) of 4-chromanone in 200 ml of ethanol. The reaction mixture was refluxed for 36 hrs., stripped in vacuo to one-half volume and cooled in the refrigerator overnight. The slurry was filtered and the white crystalline solid washed with 50 ml of isopropanol then 200 ml of ether and dried; m.p. 105-108. Yield: 44 g (68%). The filtrate was extracted with 250 ml of CHCl3, and the CHCl3 extract dried over MgSO4, filtered and stripped in vacuo.
  • 8
  • [ 491-37-2 ]
  • [ 18442-22-3 ]
YieldReaction ConditionsOperation in experiment
74% 7-Bromo-4-chromanone. Into a round bottom flask kept at 0 C., AlCl3 (0.533 g, 3.99 mmol) and, 5 mL of CH2Cl2 was added. The reaction system was put under nitrogen and stirred for about 7 minutes before adding 10 mL of a CH2Cl2 solution of 4-chromanone (0.296 g, 1.99 mmol). After the reaction mixture was stirred for 10 minutes, 10 mL of Br2 (0.352 g, 2.20 mmol) was added and, the reaction mixture was stirred at room temperature for an hour. At the end of this period of time, the reaction mixture was poured into 30 mL of ice-water and, the product was extracted 3 times from the aqueous phase with EtOAc. The resultant organic phase was washed once with brine and dried under Na2SO4. After the solvent was evaporated, the solid formed was filtered and dried to obtain 0.361 g (1.51 mmol) of the product (93% pure) in a 74% yield. 1H NMR (300 MHz, CDCl3, delta): 7.90 (dd, J=2.6, 0.3 ArH, 1H,), 7.47 (dd, J=8.8, 2.5, Ar, 1H,), 6.82 (dd, J=8.8, 0.2, Ar, 1H), 4.48 (t, J=6.5, C2, 2H), 2.75 (t, J=6.5, C2, 2H).
  • 10
  • [ 491-37-2 ]
  • [ 210488-55-4 ]
  • [ 188198-38-1 ]
  • 11
  • [ 491-37-2 ]
  • [ 256652-04-7 ]
  • [ 113486-36-5 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 491-37-2 ]

Ketones

Chemical Structure| 80096-64-6

A146805 [80096-64-6]

6-Hydroxy-chroman-4-one

Similarity: 1.00

Chemical Structure| 5802-17-5

A186956 [5802-17-5]

6-Methoxychroman-4-one

Similarity: 1.00

Chemical Structure| 39513-75-2

A347877 [39513-75-2]

6-Methylchroman-4-one

Similarity: 1.00

Chemical Structure| 42327-52-6

A146559 [42327-52-6]

7-Methoxychroman-4-one

Similarity: 0.98

Chemical Structure| 54107-66-3

A232310 [54107-66-3]

5,7-Dimethoxychroman-4-one

Similarity: 0.94

Related Parent Nucleus of
[ 491-37-2 ]

Other Aromatic Heterocycles

Chemical Structure| 80096-64-6

A146805 [80096-64-6]

6-Hydroxy-chroman-4-one

Similarity: 1.00

Chemical Structure| 5802-17-5

A186956 [5802-17-5]

6-Methoxychroman-4-one

Similarity: 1.00

Chemical Structure| 39513-75-2

A347877 [39513-75-2]

6-Methylchroman-4-one

Similarity: 1.00

Chemical Structure| 42327-52-6

A146559 [42327-52-6]

7-Methoxychroman-4-one

Similarity: 0.98

Chemical Structure| 54107-66-3

A232310 [54107-66-3]

5,7-Dimethoxychroman-4-one

Similarity: 0.94