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Structure of 29841-69-8

Chemical Structure| 29841-69-8

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Jankowska, Dominika ; Lakomska, Iwona ; Muziol, Tadeusz M ; Skowronski, Lukasz ; Rerek, Tomasz ; Popielarski, Pawel , et al.

Abstract: 3+3 optically active macrocyclic Schiff bases were synthesized in the reaction between with or (1S,2S)-(−)-1,2-diphenylethylenediamine (S1a). The new compounds were spectroscopically characterised by NMR, IR, X-ray (S1a), UV–Vis and fluorescence spectroscopy. The S1a molecule creates channels with distances between oxygen atoms ranging from 5.8-6.3 Å and sufficiently large to host acetonitrile molecule. Both compounds exhibit green-yellow emission in solution and solid state. Thin layers of the S1 compound obtained via Molecular Beam Epitaxy (MBE) were characterised by scanning electron microscopy with energy-dispersive X-ray spectroscopy SEM/EDS and atomic force microscopy (AFM). The optical properties of the S1/Si thin material were analysed using spectroscopic ellipsometry (SE), fluorescence spectroscopy and synchrotron radiation (SR). The time constant for the decay investigated under SR, denoted by τ1, was determined to be approximately 1.02 ns, suggesting a fast deactivation process of the excited electronic state in the S1/Si material. The ellipsometric analysis of the S1/Si layer showed semiconducting behaviour with pronounced absorption features in the UV range, attributed to π → π* and n → π* transitions, characteristic of Schiff bases. The band-gap energy, determined using the Tauc method, is 3.46 ± 0.01 eV. These analyses highlight the material’s potential in applications requiring precise control of optical properties. In the emission spectrum of S1a, a significant emission peak of approximately 561 nm indicates the presence of a prominent emissive process within this wavelength. The S1a compound is emissive in the yellow-green region of the spectrum and has a longer decay time, which suggests that it can be used in sensing optical technologies.

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Kaur, Gurkiran ; Dominique, Nathaniel L. ; Hu, Gaohe ; Nalaoh, Phattananawee ; Thimes, Rebekah L. ; Strausser, Shelby L. , et al.

Abstract: Controlling the chirality of mol.-surface systems is essential for applications ranging from heterogeneous catalysis to biosensing. N-heterocyclic carbenes (NHCs) are quickly becoming a dominant ligand for noble metal surface passivation, but the potential of chiral NHC scaffolds remains untapped. In this work, two stereoisomers, one C2 sym. and one Cs sym., of saturated N-heterocyclic carbenes (NHCs) and a structurally related unsaturated NHC (C2v sym.) were synthesized as NHC-CO2 adducts. These CO2-protected NHCs were deposited on gold films and their presence on the films was confirmed by laser desorption ionization mass spectrometry (LDI-MS) and surface enhanced Raman spectroscopy (SERS). Surprisingly, the Cs NHC, but not the chiral C2 NHC, partially degrades to the independently synthesized unsaturated NHC upon binding to the gold. Theor. calculations assist in explaining this phenomenon by showing that the NHCs primarily lie flat on the gold surfaces, which exposes the backbone protons on the Cs-sym. NHC to a formal elimination of H2, while the C2-sym. NHC remains protected from this elimination reaction. These results raise critical questions as to how the structure of NHC ligands may be tuned to influence binding and reactivity on gold surfaces.

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Jameson ; Bailey Lauren ;

Abstract: Enantioselective additions of malonate esters to nitroalkenes can be catalyzed by a variety of salts of chiral cobalt(III) trications [Co(1,2-diamine)3] 3+ in the presence of nitrogen donor bases in acetone. Catalysts that feature enantiopure 1,2-diphenylethylenediamine are particularly effective, and the base can also be incorporated into one of the counter anions, for example a (substituted) nicotinate. This study shows that such additions can be carried out under solvent free conditions and with reduced reaction times using ball milling, further enhancing the "green" credentials of this large family of earth-abundant-metal catalysts. The effect of various reaction variables are probed (base, counter anions, loading, time, quantity of balls, etc.), and the optimized conditions applied to twelve nitroalkenes, affording products in average yields and ee values of 89% and 74%. The enantioselectivities appear slightly lower than for analogous reactions in solution (0 °C), and possible factors and remedies are discussed. These tricationic Co(III) species were also analyzed using Electrospray Ionization-Mass Spectrometry to determine if the anions “fly” with the cation for further mechanistic analysis. Only half showed anions “flying” with the cation: Λ-(S,S)-23+ 2Cl–, Λ/D-(S,S)-23+ 2Cl–BArf –, Λ-(S,S)-23+ Cl–BArf –Nic–, and Λ-(S,S)-23+ 3BF4 –. While anionic impurities were found in several cases, the larger, bulkier anions seemed to become ionized themselves leaving no indication of intact cation-anion species post-ionization. Enhanced purification techniques are shown to improve the removal of unwanted anions.

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Connor Q. Kabes ; William J. Maximuck ; Subrata K. Ghosh ; Anil Kumar ; Nattamai Bhuvanesh ; John A. Gladysz

Abstract: The enantiopure and diastereopure salts Λ- or Δ-[Co((S,S)-dpen)3]3+ 2Cl–BArf– (Λ- or Δ-(S,S)-13+ 2Cl–BArf–; dpen/BArf = 1,2-diphenylethylenediamine/B(3,5-C6H3(CF3)2)4) and Λ-(S,S)-13+ 3Cl– are treated with salts of the enantiopure chiral monoanions (A–) or dianions (A2–) 3-bromocamphor-8-sulfonate (camphSO3–), 1,1′-binaphthyl-2,2′-diyl phosphate (and three 3,3′-disubstituted derivatives), a related biphenanthryl species, tartrate, and Sb2(tart′)22– (tart′ = [−O2C–CHO––CHO––CO2–]). The lipophilic salts Λ- or Δ-(S,S)-13+ 2A–BArf–, Λ-(S,S)-13+ A2–BArf–, and Λ-(S,S)-13+ 3A– are isolated as hydrates and characterized by NMR and microanalyses. In the presence of tertiary amines, many of these are highly enantioselective catalysts for additions of 1,3-dicarbonyl compounds to trans-β-nitrostyrene and di-tert-butylazodicarboxylate. The ee values for diastereomeric salts can exhibit significant differences (avg/high/median Δ%ee = 10/63/6; matched/mismatched effect), and in a few cases, they are better than those obtained with Λ- or Δ-(S,S)-13+ 2Cl–BArf–. The crystal structure of Δ-(S,S)-13+ 2(1S)-camphSO3–BArf– shows that the two sulfonate moieties hydrogen-bond to opposite (idealized) C3-symmetric faces of the trication, with a separate oxygen atom associated with each of the three synperiplanar NH groups.

Keywords: cobalt ; 1,2-diamines ; chiral anions ; hydrogen bonding ; enantioselective catalysis ; Michael additions ; matched/mismatched

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Alternative Products

Product Details of [ 29841-69-8 ]

CAS No. :29841-69-8
Formula : C14H16N2
M.W : 212.29
SMILES Code : N[C@@H](C1=CC=CC=C1)[C@H](C2=CC=CC=C2)N
MDL No. :MFCD00082751
InChI Key :PONXTPCRRASWKW-KBPBESRZSA-N
Pubchem ID :6931238

Safety of [ 29841-69-8 ]

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

Computational Chemistry of [ 29841-69-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 12
Fraction Csp3 0.14
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 66.12
TPSA ?

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

52.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.11
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

1.4
Log Po/w (WLOGP)?

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

1.74
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.

2.41
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

2.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.97

Water Solubility

Log S (ESOL):?

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

-2.4
Solubility 0.855 mg/ml ; 0.00403 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.

-2.1
Solubility 1.7 mg/ml ; 0.008 mol/l
Class?

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

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

-4.3
Solubility 0.0106 mg/ml ; 0.0000501 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

Yes
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.

-6.6 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

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)

1.98

Application In Synthesis of [ 29841-69-8 ]

* 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.

  • Upstream synthesis route of [ 29841-69-8 ]
  • Downstream synthetic route of [ 29841-69-8 ]

[ 29841-69-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 358-23-6 ]
  • [ 29841-69-8 ]
  • [ 121788-77-0 ]
References: [1] Tetrahedron: Asymmetry, 1995, vol. 6, # 1, p. 3 - 6.
[2] Organic Syntheses, 1993, vol. 71, p. 30 - 30.
 

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