Home Cart Sign in  
Chemical Structure| 479253-00-4 Chemical Structure| 479253-00-4

Structure of 479253-00-4

Chemical Structure| 479253-00-4

*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 [ 479253-00-4 ]

CAS No. :479253-00-4
Formula : C9H16FNO2
M.W : 189.23
SMILES Code : F[C@@H]1CN(C(OC(C)(C)C)=O)CC1
MDL No. :MFCD04114064
InChI Key :SUECTKVSIDXQQE-ZETCQYMHSA-N
Pubchem ID :18453464

Safety of [ 479253-00-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 479253-00-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 51.84
TPSA ?

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

29.54 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.53
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

1.65
Log Po/w (WLOGP)?

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

2.0
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.

1.56
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

1.18
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.78

Water Solubility

Log S (ESOL):?

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

-1.85
Solubility 2.64 mg/ml ; 0.014 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.

-1.88
Solubility 2.47 mg/ml ; 0.0131 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

-1.28
Solubility 10.0 mg/ml ; 0.053 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

No
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.

-6.28 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)

2.71

Application In Synthesis of [ 479253-00-4 ]

* 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 [ 479253-00-4 ]

[ 479253-00-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 109431-87-0 ]
  • [ 479253-00-4 ]
YieldReaction ConditionsOperation in experiment
26% With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃; for 1.25h; 1) (3S)-3-Fluoropyrrolidine-1-carboxylic acid tert-butyl ester Diethylaminosulfur trifluoride (2.22 mL) was added to a solution of (3R)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (2.62 g) in dichloromethane (50 mL) at - 78C, and the resultant mixture was stirred for 75 minutes at room temperature. The reaction solution was poured into ice water and partitioned. The organic layer was dried over anhydrous magnesium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain (3S)-3-fluoropyrrolidine-1-carboxylic acid tert-butyl ester (676 mg, 26%) as an oily product. 1H-NMR(400MHz, CDCl3)δ: 1.45(9H, s), 2.17-2.26(1H, m), 3.52-3.68(5H, m), 5.20(1H, dt, J=52.7, 3.4Hz).
With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at -78 - 20℃; Slowly add [bis(2-methoxyethyl)amino]sulfur trifluoride (2.40 mL, 13.03 mmol) to a solution of iV-Boc-(i?)-(-)-3-pyrrolidinol (2.00 g, 10.86 mmol) in anhydrous dichloromethane (10 mL), at -78 C and under nitrogen. Allow the reaction mixture to warm to room temperature and stir overnight. Carefully add an aqueous solution of sodium hydrogen carbonate (saturated, 20 mL) and extract with dichloromethane. Concentrate the combined organic extracts under vacuum then purify using automated flash chromatography (ISCO System, 120 g Redisep Si02 column; 0 - 40% ethyl acetate in cyclohexane gradient elution over 30 minutes at 85 mL/min) to give the title compound as a pale yellow liquid (1.67 g): MS (m/e): 212 (M+23).
With diethylamino-sulfur trifluoride; In 1,2-dichloro-ethane; at -30 - 20℃; for 15h; To a well stirred and cooled (-30 C) solution of Step 1 intermediate (1.5 g, 8.01 mmol) in dichloroethane (50 ml) was added diethylaminosulphur trifluoride (1.94 mg, 12.01 mmol) under nitrogen and the reaction mixture was maintained at this temperature for 1 h. The reaction mixture was EPO <DP n="49"/>gradually allowed to warm to room temperature and stirring was continued for another 14 h. The reaction mixture was poured onto a mixture of ice and solid NaHCO3 and stirred till no effervescence was seen. The mixture was diluted with water and extracted with dichloromethane (3 x 100 ml). The combined organic extracts were washed with water, brine and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (25 % ethyl acetate in petroleum ether) to give 840 mg of the desired compound as yellow oil; IR (neat) 3500, 2978, 1698, 1407 cm"1; 1H NMR (CDCl3, 300 MHz) δ 1.44 (s, 9H), 1.89-2.28 (m, 2H), 3.44-3.77 (m, 4H), 5.11-5.31 (m, IH).
With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 0 - 20℃; for 1h; To a solution OF 3- (R)-HYDROXY-PYRROLIDINE-1-CARBOXYLIC acid ter-butyl ester (200mg) in CH2CI2 (10ML) is added [bis (2-methoxyethyl) AMINO] SULFER TRIFLUORIDE (236uL) at 0C, and stirred for 1HR at room temperature. The reaction mixture is poured in aqueous NaHC03 and extracted with Et20. The organic layer is successively washed with H20 and aqueous NACI, dried over MgS04, and concentrated in vacuo. The residue is purified by column chromatography to give a colorless oil.

 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 479253-00-4 ]

Fluorinated Building Blocks

Chemical Structure| 620611-27-0

A207532 [620611-27-0]

tert-Butyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate

Similarity: 0.91

Chemical Structure| 2055223-76-0

A192981 [2055223-76-0]

cis-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1174020-30-4

A242039 [1174020-30-4]

(3S,4R)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1431720-86-3

A346802 [1431720-86-3]

cis-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1290191-73-9

A240349 [1290191-73-9]

(3S,4R)-tert-Butyl 3-amino-4-fluoropiperidine-1-carboxylate

Similarity: 0.86

Amides

Chemical Structure| 620611-27-0

A207532 [620611-27-0]

tert-Butyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate

Similarity: 0.91

Chemical Structure| 2055223-76-0

A192981 [2055223-76-0]

cis-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1174020-30-4

A242039 [1174020-30-4]

(3S,4R)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1431720-86-3

A346802 [1431720-86-3]

cis-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1290191-73-9

A240349 [1290191-73-9]

(3S,4R)-tert-Butyl 3-amino-4-fluoropiperidine-1-carboxylate

Similarity: 0.86

Related Parent Nucleus of
[ 479253-00-4 ]

Pyrrolidines

Chemical Structure| 2055223-76-0

A192981 [2055223-76-0]

cis-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1174020-30-4

A242039 [1174020-30-4]

(3S,4R)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 1431720-86-3

A346802 [1431720-86-3]

cis-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 86953-79-9

A164609 [86953-79-9]

tert-Butyl pyrrolidine-1-carboxylate

Similarity: 0.84

Chemical Structure| 1408074-83-8

A230176 [1408074-83-8]

tert-Butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate

Similarity: 0.84