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Chemical Structure| 135884-31-0 Chemical Structure| 135884-31-0

Structure of N-Boc-2-pyrroleboronic acid
CAS No.: 135884-31-0

Chemical Structure| 135884-31-0

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Product Citations

Product Citations

Riahin, Connor ; Mendis, Kushani ; Busick, Brandon ; Ptaszek, Marcin ; Yang, Mengran ; Stacey, Gary , et al.

Abstract: Semiconducting polymer dots (Pdots) are rapidly becoming one of the most studied nanoparticles in fluorescence bioimaging and sensing. Their small size, high brightness, and resistance to photobleaching make them one of the most attractive fluorophores for fluorescence imaging and sensing applications. This paper highlights our recent advances in fluorescence bioimaging and sensing with nanoscale luminescent Pdots, specifically the use of organic dyes as dopant molecules to modify the optical properties of Pdots to enable deep red and near infrared fluorescence bioimaging applications and to impart sensitivity of dye doped Pdots towards selected analytes. Building on our earlier work, we report the formation of secondary antibody-conjugated Pdots and provide Cryo-TEM evidence for their formation. We demonstrate the selective targeting of the antibodyconjugated Pdots to FLAG-tagged FLS2 membrane receptors in genetically engineered plant leaf cells. We also report the formation of a new class of luminescent Pdots with emission wavelengths of around 1000 nm. Finally, we demonstrate the formation and utility of oxygen sensing Pdots in aqueous media.

Keywords: near infrared emission ; polymer dots ; plant cell imaging ; sensing

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Product Details of [ 135884-31-0 ]

CAS No. :135884-31-0
Formula : C9H14BNO4
M.W : 211.02
SMILES Code : O=C(N1C(B(O)O)=CC=C1)OC(C)(C)C
MDL No. :MFCD01318939
InChI Key :ZWGMJLNXIVRFRJ-UHFFFAOYSA-N
Pubchem ID :2734321

Safety of [ 135884-31-0 ]

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

Computational Chemistry of [ 135884-31-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 5
Fraction Csp3 0.44
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 56.46
TPSA ?

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

71.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

0.87
Log Po/w (WLOGP)?

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

-0.05
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.

-0.25
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

-1.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.21

Water Solubility

Log S (ESOL):?

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

-1.68
Solubility 4.42 mg/ml ; 0.0209 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.

-1.96
Solubility 2.32 mg/ml ; 0.011 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

-0.58
Solubility 55.5 mg/ml ; 0.263 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

No
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.

-6.97 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.

0.55

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)

2.48

Application In Synthesis of [ 135884-31-0 ]

* 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 [ 135884-31-0 ]

[ 135884-31-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1333-74-0 ]
  • [ 135884-31-0 ]
  • [ 149682-75-7 ]
  • 2
  • [ 18995-35-2 ]
  • [ 135884-31-0 ]
  • [ 1158985-03-5 ]
  • 3
  • [ 59237-53-5 ]
  • [ 135884-31-0 ]
  • [ 1263408-64-5 ]
YieldReaction ConditionsOperation in experiment
42.6% With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In 1,4-dioxane; at 100℃; for 1h; To a suspension of methyl 6-chloro-5 -nitronicotinate (0.108 g, 0.499 mmol), l-Boc-pyrrole-2- boronic acid (0.210 g, 0.997 mmol), and trans-Dichlorobis(triphenylphosphine)palladium (II) (0.350 g, 0.499 mmol) in Dioxane (Volume: 2.3 mL) was added 2M Sodium carbonate (0.798 mL, 1.596 mmol) at 23 0C. The reaction was stirred at 100 0C for 1 hr. The resulting suspension was filtered and rinsed with dioxane and H2O. The filtrate was diluted with EtOAc (20 mL) and the layers were separated. The organic phase was washed with saturated NaHCpsi3 and brine, dried over MgSO4, filtered, rinsed with EtOAc, and dried in vacuo. The resulting crude material was purified via medium pressure chromatography using a gradient eluant Of CH2Cl2ZMeOH. The appropriate fractions were combined and concentrated via rotary evaporation to provide methyl 6-(l -(tert-butoxycarbonyl)- IH- pyrrol-2-yl)-5 -nitronicotinate (0.0738 g, 0.212 mmol, 42.6 percent yield) as an orange gummy solid. 1H NMR (400 MHz, DMSO-J6) delta ppm 1.32 (s, 9 H) 3.96 (s, 3 H) 6.41 (t, J=3.28 Hz, 1 H) 6.65 (dd, J=3.28, 1.77 Hz, 1 H) 7.50 (dd, J=3.28, 1.77 Hz, 1 H) 8.82 (d, J=I.77 Hz, 1 H) 9.33 (d, J=I.77 Hz, 1 H). ESI-MS: m/z 348.2 (M+H)+.
  • 4
  • [ 129013-83-8 ]
  • [ 135884-31-0 ]
  • C20H20N2O2 [ No CAS ]
  • 5
  • [ 39795-60-3 ]
  • [ 135884-31-0 ]
  • C20H20N2O2 [ No CAS ]
  • 6
  • [ 19063-55-9 ]
  • [ 135884-31-0 ]
  • C18H17NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In N,N-dimethyl-formamide; at 20 - 60℃; for 3h;Inert atmosphere; General procedure: 18 (138.5mg, 0.47mmol) was added to a solution of boronic acid (304.5mg, 1.44mmol), cesium fluoride (303mg, 1.99mmol), and PdCl2(dppf) (81.2mg, 0.10mmol) in dry DMF (5mL) at room temperature under argon. The reaction mixture was heated at 60C for 3h, then neutralized with ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica gel, AcOEt/n-hexane=1:4) to give 23 (129mg, 72%). Compounds 22 and 24 were synthesized similarly from compounds 14 and 21, respectively.
  • 7
  • [ 5460-32-2 ]
  • [ 135884-31-0 ]
  • 2-(3,4-dimethoxyphenyl)-1H-pyrrole [ No CAS ]
  • C17H21NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); CyJohnPhos; In ethanol; water;Inert atmosphere; Reflux; 4-Iodo-1,2-dimethoxybenzene (5; 16.7 g, 63.3 mmol) was dissolved in EtOH (63 mL), Boc-pyrroleboronic acid (4; 20.0 g, 94.8 mmol, 1.5 equiv) was added to the solution followed by the addition of an aqueous solution of K2CO3 (17.5 g, 126.8 mmol, 2 equiv; in 63 mL H2O). Under a constant flow of N2, CyJohnPhos (378 mg, 2 mol%) was added followed by Pd(dba)2 (364 mg, 1 mol%). The reaction mixture was vigorously stirred and heated under reflux for 4-5 h. The reaction mixture was cooled to r.t. and extracted with hexane (3 x 100 mL). The organic layer was dried over Na2SO4 and evaporated. To the residue (contains aryl iodide, Boc-pyrrole and product ~1:1:1) was added freshly prepared (from Na and MeOH) NaOMe solution (~1 M in MeOH, 3-5 equiv) and the mixture was left overnight. The reaction mixture was diluted with H2O and extracted with Et2O (3 x 100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was triturated with hexane and filtered off to give pure enough compound.
  • 8
  • [ 135884-31-0 ]
  • [ 149682-75-7 ]
  • 9
  • [ 1753-75-9 ]
  • [ 135884-31-0 ]
  • C15H15N3O2S [ No CAS ]
  • 10
  • [ 13667-12-4 ]
  • [ 135884-31-0 ]
  • C23H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; palladium diacetate; XPhos; In butan-1-ol; for 2h;Inert atmosphere; General procedure: To a flame-dried 5 mL microwave vial flask equipped with a magnetic stir bar was added N-Boc-pyrrole-2-boronic acid (316 mg,1.5 mmol, 1.5 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 0.02 equiv), XPhos (19.0 mg, 0.04 mmol, 0.04 equiv), K3PO4 (424 g, 2.0 mmol, 2.0 equiv), and aryl bromide (1.0 mmol, 1.0 equiv). The flask was evacuated and backfilled with nitrogen three times, and then the gas line adapter was quickly replaced with a rubber septum and a balloon of nitrogen. To the flask was added degassed (by sonicationfor 30 min with N2 sparging), anhydrous n-butanol [2 mL (0.5M in ArBr)]. The heterogeneous reaction mixture was stirred vigorously for 2 h and then poured into ethyl acetate (~20 mL). This mixture was filtered through a pad of silica and concentrated under reduced pressure by rotary evaporation. This product was used without further purification.
  • 11
  • [ 6287-82-7 ]
  • [ 135884-31-0 ]
  • C26H28N2O4S [ No CAS ]
 

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Technical Information

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