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Chemical Structure| 4286-55-9 Chemical Structure| 4286-55-9

Structure of Hexamethylene bromohydrin
CAS No.: 4286-55-9

Chemical Structure| 4286-55-9

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Lewis, Kristin L ; Hoang, Jonathan D ; Aye, Sarah S ; Kennedy, David T ; Toney, Michael F ; White, Timothy J

Abstract: The directional deformation of liquid crystalline elastomers (LCEs) is predicated on alignment, enforced by variousprocessing techniques. Specifically, surface-aligned LCEs can exhibit higher temperature thermomechanical responses and weakenedstrain−temperature coupling in comparison to LCEs subjected to mechanical or rheological alignment. Recently, we reportedenhanced stimuli response of mechanically aligned LCEs containing supramolecular liquid crystals. Here, we prepare supramolecularLCEs via surface-enforced alignment to study the impact of the supramolecular bond strength and intermolecular forces. This wasevaluated using oxybenzoic acid (OBA) derivatives with and without pendant methyl groups as well as via oxybenzoic acid-pyridinecomplexes. Increased incorporation of supramolecular mesogens reduces the isotropic transition temperature and generally increasesthe strain−temperature coupling. The number of elastically active strands per unit volume, hydrogen bond conformations, andnetwork morphology are affected by the supramolecular mesogens and influence the observed stimuli response. Overall, reducedintermolecular interactions correlate with more desirable actuation properties, demonstrating the influence of the supramolecularmesogen’s structure.

Purchased from AmBeed:

BRIAN P. RADKA ;

Abstract: Dynamic reconfiguration of optical materials has and continues to be of significant interestin technological utility in displays, healthcare, automotive, aerospace, and architecture. This thesis is concerned with so-called “polymer stabilized” cholesteric liquid crystals (PSCLCs), material systems in which application of an electric field can adjust the position or bandwidth of a selective reflection. These material systems are based upon the cholesteric liquid crystal (CLC) phase, which nascently self-organizes into a periodic helical structure in which refractive index modulation results in a polarization-specific Bragg reflection. Depending on material composition, application of an electric field to a CLC can result in reflection switching or “tuning” (e.g., shift in reflection wavelength) but typically these electro-optic responses are limited in magnitude or response time (often taking days for the reflection to recover). Comparatively, the integration of small concentrations of polymer, to “stabilize” the CLC phase, creates a material system that can undergo a dynamic and reversible electro-optic response. This thesis extends upon a number of prior examinations (generally focused on phenomena or functionality) undertaken at the Air Force Research Laboratory, that have demonstrated myriad responses including reflection bandwidth broadening, reflection wavelength tuning, and switching. The systematic investigations presented in this thesis directly elucidate the underlying electromechanical mechanism that is critical to enabling further optimization and enhancement of electro-optic response necessary for implementation in functional utility in applications. More specifically, the first aim of this thesis focuses on the formation and importance of the retention of structural chirality in the polymer stabilizing network (PSN) and the intermolecular interactions between the PSN and the non-reactive CLC host. Notably, PSCLCs prepared with non-liquid-crystalline polymer networks confirm that the chiral templating does not require the monomeric precursors to be liquid crystalline. Further, the cation-mediated electromechanical response of the deformation of the polymer network was correlated to be directly associated with the host (via distinctive confocal fluorescent experiments). The second aim of this thesis is focused on identifying and understanding the interactions between the polymer network and ions, through exploring the electrochemical properties in addition to the electro-optic response. The effect of polymerization on the electrical properties was investigated through impedance spectroscopy with mixtures prepared with metallic salts, ionic liquids, and ionic polymers. The electrical properties of these formulations were then correlated to the electro-optic response of PSCLCs prepared from them. Finally, informed by these fundamental studies, this thesis explored the molecular engineering of the polymer stabilizing network. This was achieved in two ways, both focused on affecting the crosslink density of the PSN. In the first, a dithiol additive was incorporated into the polymer network through copolymerization with the acrylate functionalized liquid crystalline monomer. This reaction decreases the crosslink density through both chain extension and chain transfer. Compositional studies isolated an optimum crosslink density/concentration to retain structural chirality with maximal elasticity. Second, a monofunctional liquid crystalline monomer was incorporated into the polymer network to decrease crosslink density while retaining high liquid crystalline character in the polymer network. The electromechanical mechanism in this material system enabled the realization of a new electro-optic phenomena in PSCLCs, reflection notch splitting

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 4286-55-9 ]

CAS No. :4286-55-9
Formula : C6H13BrO
M.W : 181.07
SMILES Code : OCCCCCCBr
MDL No. :MFCD00002983
InChI Key :FCMCSZXRVWDVAW-UHFFFAOYSA-N
Pubchem ID :77970

Safety of [ 4286-55-9 ]

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

Computational Chemistry of [ 4286-55-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 5
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 39.99
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.2
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

1.73
Log Po/w (WLOGP)?

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

1.93
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.

2.06
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

1.93
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.

-1.72
Solubility 3.43 mg/ml ; 0.0189 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.

-1.77
Solubility 3.07 mg/ml ; 0.0169 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

-2.58
Solubility 0.471 mg/ml ; 0.0026 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.

-6.18 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

2.0
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)

2.54

Application In Synthesis of [ 4286-55-9 ]

* 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 [ 4286-55-9 ]

[ 4286-55-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4286-55-9 ]
  • [ 57473-33-3 ]
  • 7-chloro-1-(6-hydroxyhexyl)imidazo<1,2-a>pyrimidin-5-one [ No CAS ]
  • 2
  • [ 4286-55-9 ]
  • [ 4877-80-9 ]
  • 2,3,6,7,10,11-hexakis(6-hydroxyhexyloxy)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.5% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 20h;Reflux; 2,3,6,7,10,11-Hexakis(6-hydroxyhexyloxy)triphenylene(1): 2,3,6,7,10,11-Hexahydroxytriphenylene hydrate (1 g,3.0 mmol) and K2CO3 (8.5 g, 61.6 mmol) were added to aflask containing dimethylformamide (DMF, 100 mL) andheated at 80 oC. A solution of 6-bromo-1-hexanol (5.5 g,30.8 mmol) in DMF (20 mL) was added dropwise to thereaction mixture, and the resulting mixture was refluxed for20 h. Then, the reaction mixture was cooled to room temperature,and ethyl acetate (100 mL) was added and stirred for30 min. Brine (20 mL) was added, and the organic layer wasseparated twice. The combined organic layer was dried overanhydrous MgSO4, and the solvent was evaporated underreduced pressure. The crude product was purified by silicacolumn chromatography. (CH2Cl2:MeOH = 13:2) Yield:2.18 g (78.5percent). 1H NMR (200 MHz, CDCl3) delta 1.45-1.73 (m,36H), 1.86-2.06 (m, 12H), 3.68 (t, J = 6.4 Hz, 12H), 4.24 (t,J = 6.2 Hz, 12H), 7.82 (s, 6H).
  • 5
  • [ 4286-55-9 ]
  • [ 605-32-3 ]
  • hydroxyhexyloxyanthraquinone [ No CAS ]
  • 6
  • [ 6933-49-9 ]
  • [ 4286-55-9 ]
  • N-(6-hydroxyhexyl)-2-methoxycarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dimethyl sulfoxide; at 65℃; for 4h; 2.97 g (10 mmol) of <strong>[6933-49-9]2-methoxycarbazole</strong> and 150 mg of benzyltriethylammonium chloride were sequentially added to a single-necked flask.25 ml of dimethyl sulfoxide, 20 ml of saturated sodium hydroxide solution, and 1.57 ml (12 mmol) of 6-bromo-n-hexanol.The reaction was carried out at 65 C for 4 h under magnetic stirring.Add 100 ml of deionized water, 100 ml of ethyl acetate, separate the liquid, and wash the organic phase several times with water until the solution is neutral (usually 3 times).The organic phase was separated and dried over anhydrous sodium sulfate.The residue was separated on silica gel column chromatography (eluent: dichloromethane).Drying at 35 C for 24 h under vacuum to give a white solidN-(6-hydroxyhexyl)-<strong>[6933-49-9]2-methoxycarbazole</strong> 2.54 g, yield 90%.
90% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dimethyl sulfoxide; at 65℃; for 4h; 1.97 g (10 mmol) of methoxycarbazole was sequentially added to a one-necked flask.Benzyltriethylammonium chloride 150mg, dimethyl sulfoxide 20ml, saturated sodium hydroxide 15ml,1.57 ml (12 mmol) of 6-bromo-n-hexanol was reacted at 65 C for 4 h with magnetic stirring.Add 100 ml of deionized water, 100 ml of ethyl acetate, separate the liquid, and wash the organic phase several times with water until the solution is neutral (generally3 times),The organic layer was separated and dried over anhydrous sodium sulfate.The white solid N-(6-hydroxyhexyl)methoxycarbazole was isolated in 2.7 g, yield 90%.
 

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