Home Cart Sign in  
Chemical Structure| 270596-42-4 Chemical Structure| 270596-42-4

Structure of 270596-42-4

Chemical Structure| 270596-42-4

*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 [ 270596-42-4 ]

CAS No. :270596-42-4
Formula : C15H20ClNO4
M.W : 313.78
SMILES Code : O=C(O)C[C@@H](NC(OC(C)(C)C)=O)CC1=CC=C(Cl)C=C1
MDL No. :MFCD01318372
InChI Key :XHNLLTGZBXJRGH-LBPRGKRZSA-N
Pubchem ID :2761571

Safety of [ 270596-42-4 ]

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

Computational Chemistry of [ 270596-42-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 6
Fraction Csp3 0.47
Num. rotatable bonds 8
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 81.16
TPSA ?

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

75.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.82
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

3.08
Log Po/w (WLOGP)?

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

3.25
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.

2.74
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

2.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.92

Water Solubility

Log S (ESOL):?

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

-3.41
Solubility 0.122 mg/ml ; 0.00039 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.

-4.34
Solubility 0.0145 mg/ml ; 0.0000462 mol/l
Class?

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

Moderately 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

-4.18
Solubility 0.0208 mg/ml ; 0.0000662 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

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

Yes
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.

-6.03 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

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

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)

2.81

Application In Synthesis of [ 270596-42-4 ]

* 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 [ 270596-42-4 ]

[ 270596-42-4 ] Synthesis Path-Downstream   1~1

YieldReaction ConditionsOperation in experiment
With palladium on carbon; hydrogen; In methanol; under 68404.6 Torr; for 24.0h; General procedure: A method similar to that of Example 1 was carried out. The starting material was 3-fluoroallylbenzene (1.36 g, 10 mmol) (R) -N-Boc-3-amino-4- (3-fluorophenyl) -butyric acid (1.78 g, 87% ee). The total yield was 60%.Allylbenzene (1.18 g, 10 mmol), Crotonaldehyde (1.4 g, 2 mmol) and Grubbs second-generation catalyst (9 mg, 0.01 mol, 0.1 mol%) Was dissolved in dichloromethane (20 mL) The reaction solution was cooled to 0 C for 12 hours; Hydroxylamine (1.59 g, 12 mmol) protected by Boc was added in turn followed by nitrogen atom, S configuration of oxygen is trimethylsilane protected alpha, alpha-diphenyl proline (330 mg, 1 mmol, 10 mol%) and p-nitrobenzoic acid (160 mg, 1 mmol, 10 mol%), The reaction mixture was stirred at 0 C for 15 hours. Removal of solvent methylene chloride; Acetonitrile (10 mL), Aqueous NaH2PO4 solution (240 mg NaH2PO4, 5 ml water) and H2O2 (35W% aqueous solution, 1.4 ml, 14 mmol) was added to the above residue; The reaction solution was added dropwise at 10 C to an aqueous solution of NaClO2 (1.27 g NaClO2, 14 mmol, 14 m water). After 3 hours, methylene chloride (20 ml) was added to dilute the reaction solution, The organic phase was washed with saturated sodium bicarbonate (5 ml) and Saturated sodium chloride (5 ml) was washed once and then dried over anhydrous sodium sulfate. Filtered and concentrated column chromatography (PE / EtOAc, 5: 1-3: 1) (R) -N-Boc-3-benzyl-5-hydroxyisoxazole (1.98 g, 71% yield), 92% ee. (R) -N-Boc-3-benzyl-5-hydroxyisoxazole (1.98 g, 7.1 mmol, 92% ee) was dissolved in methanol (50 mL) Pd / C (20% w / w, 550 mg) was added and hydrogenated at 90 atm for 24 hours. filter, (R) -N-Boc-3-amino-4-phenyl-butyric acid (1.96 g, 92% ee) to give a total yield of 70%.
 

Historical Records

Technical Information

Categories