Home Cart Sign in  
Chemical Structure| 196799-45-8 Chemical Structure| 196799-45-8

Structure of 196799-45-8

Chemical Structure| 196799-45-8

*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 [ 196799-45-8 ]

CAS No. :196799-45-8
Formula : C9H8O2
M.W : 148.16
SMILES Code : O=CC1=C(OCC2)C2=CC=C1
MDL No. :MFCD06200853
InChI Key :CLXXUGOCVBQNAI-UHFFFAOYSA-N
Pubchem ID :2795018

Safety of [ 196799-45-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 196799-45-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 41.17
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.

1.77
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

1.39
Log Po/w (WLOGP)?

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

1.43
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

2.65
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.

-1.97
Solubility 1.58 mg/ml ; 0.0107 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.55
Solubility 4.22 mg/ml ; 0.0285 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

-2.62
Solubility 0.358 mg/ml ; 0.00242 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

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)

1.78

Application In Synthesis of [ 196799-45-8 ]

* 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 [ 196799-45-8 ]

[ 196799-45-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 35700-40-4 ]
  • [ 128625-52-5 ]
  • [ 4490-81-7 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; EXAMPLE 206 STR276 2,3-Dihydrobenzofuran-7-carboxaldehyde A solution of 2,3-dihydrobenzofuran-7-carboxylic acid (1.0 g, 6.09 mmol, 1.0 equiv.), dimethylmethoxyamine hydrochloride (654 mg, 6.7 mmol, 1.1 equiv.), diisopropylethylamine (DIEA) (2.35 ml, 13.4 mmol, 2.2 equiv.), benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP) (3.48 g, 6.7 mmol, 1.1 equiv.) and 4-dimethylaminopyridine (DMAP) (74 mg, 0.67 mmol, 0.1 equiv.) in anhydrous THF (20 ml) was stirred for 18 hr under argon. The reaction mixture was then diluted with EtOAc (100 ml) and washed with aqueous sat. NaHCO3 (2*150 ml) and aqueous 1N HCl (2*150 ml), the oragnic layer was dried over MgSO4, filtered and solvent removed. yield: 1.06 mg, 84%. LS-MS calcd 207, found 208.
  • 2
  • [ 151155-53-2 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
77% With manganese(IV) oxide; In toluene; at 60℃; for 3h; A mixture of <strong>[151155-53-2](2,3-dihydrobenzofuran-7-yl)methanol</strong> (9.76 g, 64.99 mmol) and manganese dioxide (45.2 g, 519.93 mmol) in toluene (250 mL) was stirred at 60C for 3 hr. The manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The precipitate was collected by filtration and washed with cooled hexane to give 2,3-dihydrobenzofuran-7-carbaldehyde (7.43 g, 50.1 mmol, 77%) as a pale yellow solid.
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h; [00323] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 mL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column EPO <DP n="307"/>with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h; [0359] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 rtiL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
  • 3
  • [ 196799-45-8 ]
  • [ 151155-53-2 ]
YieldReaction ConditionsOperation in experiment
2,3-Dihydro-benzofuran-7-carbaldehyde (1.50 g, 10.20 mmol) was dissolved in ether, then cooled to 0 C., NaBH4 (400 mg, 10.57 mmol) in MeOH (5.00 mL) was added. The resulting reaction mixture was stirred for 30 min, then saturated ammonium chloride was added. The mixture was extracted with ether, and the combined organic phases were washed with brine, then dried over magnesium sulfate and concentrated to afford the desired alcohol
  • 4
  • [ 35700-40-4 ]
  • [ 79-22-1 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; triethanolamine; 4,5-dichloro-1-phenylpyridazin-6-one; In tetrahydrofuran; water; ethyl acetate; Preparation of 2,3-dihydrobenzofuran-7-carbaldehyde 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved in THF (10 mL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hr. The white precipitates were removed by filtration, the filtrate was added to a solution of NaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DGM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hrs at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
  • 6
  • [ 68-12-2 ]
  • [ 206347-30-0 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
94% 7-Bromo-2,3-dihydrobenzofuran (74A) under nitrogen protection(2.0g, 10.05mmol) dissolved in tetrahydrofuran(20 mL), cooled to -78 C, n-butyl lithium (4.5 mL, 11.05 mmol)Add dropwise to the reaction, and add the stirring reaction for 0.5 hours.Further, N,N-dimethylformamide (1.1 g, 15.07 mmol) was added dropwise to the reaction.Continue to react for 1 hour. The reaction solution was quenched with saturated aqueous ammonium chloride (50 mL).The aqueous phase was extracted with ethyl acetate (30 mL×3).Wash with saturated sodium chloride solution (50 mL), dry over anhydrous sodiumAfter the filtrate is concentrated, the crude product is subjected to column chromatography.(Petroleum ether/ethyl acetate (v/v) = 10:1 to 4:1) to give an oily liquid 2,3-dihydrobenzofuran-7-carbaldehyde (74B)(1.4 g, yield: 94%).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 196799-45-8 ]

Aldehydes

Chemical Structure| 209256-42-8

A278211 [209256-42-8]

2,3-Dihydrobenzofuran-4-carbaldehyde

Similarity: 0.96

Chemical Structure| 5397-82-0

A917690 [5397-82-0]

Dibenzofuran-2-carboxaldehyde

Similarity: 0.92

Chemical Structure| 58026-14-5

A102438 [58026-14-5]

4-(Benzyloxy)-2-methoxybenzaldehyde

Similarity: 0.90

Chemical Structure| 55745-70-5

A106859 [55745-70-5]

2,3-Dihydrobenzofuran-5-carbaldehyde

Similarity: 0.88

Chemical Structure| 101093-56-5

A118309 [101093-56-5]

4-(Benzyloxy)-2-methylbenzaldehyde

Similarity: 0.88

Related Parent Nucleus of
[ 196799-45-8 ]

Benzofurans

Chemical Structure| 209256-42-8

A278211 [209256-42-8]

2,3-Dihydrobenzofuran-4-carbaldehyde

Similarity: 0.96

Chemical Structure| 170730-06-0

A211765 [170730-06-0]

1-(2,3-Dihydro-7-benzofuranyl)ethanone

Similarity: 0.92

Chemical Structure| 35700-40-4

A253731 [35700-40-4]

2,3-Dihydrobenzofuran-7-carboxylic acid

Similarity: 0.90

Chemical Structure| 55745-70-5

A106859 [55745-70-5]

2,3-Dihydrobenzofuran-5-carbaldehyde

Similarity: 0.88

Chemical Structure| 83751-12-6

A243485 [83751-12-6]

Ethyl 2,3-dihydrobenzofuran-5-carboxylate

Similarity: 0.85