3780-50-5

Usage

Chemical Properties

White powder

InChI:InChI=1/C14H22O2/c1-2-3-4-5-6-7-12-16-14-10-8-13(15)9-11-14/h8-11,15H,2-7,12H2,1H3

Upstream product

• 111-87-5 octanol 
• 123-31-9 hydroquinone 
• 111-83-1 1-bromo-octane 
• 103-16-2 4-Benzyloxyphenol 
• 67399-80-8 1-(benzyloxy)-4-(octyloxy)benzene 
• 3386-35-4 1-octyl p-toluenesulfonate 
• 30008-10-7 sodium 4-hydroxybenzen-1-olate 

Downstream Products

• 148731-17-3 4-octyloxyphenyl 4-(benzyloxy)benzoate 
• 72213-09-3 di-(4'-n-octyloxyphenyl)-trans-cyclohexane-1,4'-dicarboxylate 
• 119871-97-5 Bromo-acetic acid 4-octyloxy-phenyl ester 
• 114833-33-9 Dimethyl-thiocarbamic acid O-(4-octyloxy-phenyl) ester 
• 128895-57-8 4-(octyloxy)phenyl 4-bromobenzoate 
• 76563-19-4 4-n-octyloxyphenyl 4-n-decyloxybenzoate 
• 60127-45-9 4-Butoxy-benzoic acid 4-octyloxy-phenyl ester 
• 50649-53-1 p-n-octyloxyphenyl p-n-hexyloxybenzoate 
• 50649-57-5 4-n-Octyloxy-phenyl-4'-n-octyloxy-benzoat 
• 203256-88-6 4-(Tetrahydro-pyran-2-yloxy)-benzoic acid 4-octyloxy-phenyl ester 

Relevant academic research and scientific papers

Constitutional Isomers of Pentahydroxy-Functionalized Pillar[5]arenes: Synthesis, Characterization, and Crystal Structures

We herein report the preparation of constitutional isomers of pentahydroxy-functionalized pillar[5]arenes via the deprotection of their benzylated derivatives by catalytic hydrogenation. The structures of the obtained isomers were then established using single crystal X-ray diffraction. We also found that the yield distribution of the different constitutional isomers was dependent on the nature of the substitution, as revealed by HPLC analysis of the crude mixture. Finally, further characterization of the separated constitutional isomers indicated that they possess different melting points, NMR spectra, crystal structures, and stacking patterns in the solid state.

Surfactant compositions and use thereof as inverter of water-in-oil emulsion polymers

Surfactants capable of releasing and/or dissolving polymers to form water-soluble or water-dispersible polymer solutions are disclosed. In addition, polymer compositions containing a water-in-oil emulsion comprising the surfactant are provided and can be used, for example, in methods of dissolving a polymer. These surfactants and polymer compositions can be used in various industries including for water clarification, papermaking, sewage and industrial water treatment, drilling mud stabilizers, and enhanced oil recovery.

Gigantic Porphyrinic Cages

Due to the existing challenges in the synthesis of covalently linked large organic cages, the potential benefits of such gigantic structures have been less explored, comparatively. Here, we present a one-pot, template-free strategy to construct a porphyrin-based gigantic organic cage P12L24, built with 12 square-shaped porphyrins (P) and 24 bent linkers (L). Single crystal X-ray analysis of P12L24 revealed a cuboctahedron structure with a diameter of ～5.3 nm reminiscent of the COPII protein with a cuboctahedral geometry. To the best of our knowledge, it represents the largest, pure organic synthetic cage reported so far. By virtue of its large voids facilitating mass transport of substrates, 3a efficiently catalyzes the photooxidation of dihydroxynaphthalene derivatives in a heterogeneous setting, corroborating the benefits of these structures. Additionally, we demonstrate the insertion of a linear guest molecule into Zn-metallated cage Zn-3b in solution, which may facilitate the synthesis of multivariate gigantic cages in the future. A bottom-up self-assembly process has been a promising tool to mimic structurally complex natural architectures, e.g., the bacteriochlorophyll-based macrocyclic arrays in natural light-harvesting systems and gigantic hollow assemblies, such as ferritin, COPII cage, and other viral capsids. Nevertheless, there is still a long way to go before we can astutely program multiple building blocks to form predesigned structures. In this context, the reported examples related to atomically precise multiporphyrinic arrays and cages are limited by their tedious synthesis, poor yield and solubility, atomic-scale characterization, and small-sized cavities. Here, we report a strategy to synthesize gigantic porphyrinic cages (～5.3 nm) with 36 components and demonstrate its potential applications in processes such as heterogeneous photocatalysis and guest encapsulation. Our strategy may establish a cornerstone toward the construction of higher level, covalently bonded multiporphyrinic molecular containers. Porphyrin-based 3D molecular architectures encompassing a confined internal void have comparatively been less explored, despite their potential benefits. Here, we report a rational one-pot, template-free strategy for constructing a 5.3 nm porphyrin-based gigantic organic cage P12L24, which is reminiscent of the structure of COPII protein cuboctahedral cages. To the best of our knowledge, this is the largest purely organic cage reported so far. P12L24 efficiently catalyzes the photooxidation of dihydroxynaphthalene derivatives, thereby confirming the benefit of these gigantic structures with mesoscopic channels. Furthermore, we demonstrate the insertion of a long pillar linker (～4 nm in length) into Zn-P12L24 in solution. We believe that our strategy may establish a new direction toward the construction of higher level, covalently bonded multiporphyrinic cages.

A well-defined unimolecular channel facilitates chloride transport

A unimolecular ion channel was optimized by functionalization with a new type of rigid-rod oligomer. The macrocycle pendant endows chloride selectivity and the fluorescence feature and suitable length of the rod facilitates the visual insertion of channels into the lipid bilayer, resulting in efficient ion transport with an EC50 value of 0.36 μM.

Production of alkoxyphenol (by machine translation)

[Problem] The carbon number of 6 or higher aliphatic alcohol when used as a raw material, byproduct formation is suppressed, high yield, low cost method for manufacturing alkoxyphenol are obtained. [Solution] For the production of intense study alkoxyphenol, solvent and in the presence of an acid catalyst, a dihydric phenol with an aliphatic alcohol dehydration condensation reaction. [Drawing] no (by machine translation)

METHOD OF PURIFYING ALKOXYPHENOL

PROBLEM TO BE SOLVED: To provide a purifying method that can easily remove a dialkoxybenzene from a crude composition containing an alkoxyphenol, to obtain a high-purity alkoxyphenol, and a production method that allows a high-purity alkoxyphenol to be obtained. SOLUTION: After a C1-5 lower alcohol is added to a crude composition containing an alkoxyphenol, represented by formula (1), and insoluble matter is subjected to solid-liquid separation (where R is a C6-20 alkyl group). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Preparation and application of asymmetric poly(phenyleneethynylene) oligomer with ion transmembrane transfer activity

The invention relates to preparation and application of an asymmetric poly(phenyleneethynylene) oligomer with ion transmembrane transfer activity. The asymmetric poly(phenyleneethynylene) oligomer has a structural formula shown as the formula I (please see the formula I in the description), wherein R1 is selected from one of -CH2(CH2)4CH3, -CH2(CH2)6CH3, -CH2(CH2)8CH3, -CH2(CH2)10CH3, -OCH2CH2OCH2CH2O(CH2)5CH3 and -OCH2CH2OCH2CH2O(CH2)7CH3, R2 represents a cation recognition group or an anion recognition group, the cation recognition group is selected from one of benzo-15-crown-5, benzo-18-crown-6, hybridized nitrogen-15-crown-5, hybridized nitrogen-18-crown-6, dibenzo-15-crown-5 and dibenzo-18-crown-6, and the anion recognition group is selected from one of 2,6-pyridine diamide and isophthalic diamide. According to the asymmetric poly(phenyleneethynylene) oligomer, a single-molecule artificial ion channel is formed in a bi-layer membrane, ion transmembrane transfer is effectively achieved, a new method is sought for treating diseases related to function disorders of the ion channel, and the important application value in the field of antibacterial and anti-cancer biological medicine for treating diseases is achieved.

Intramolecular charge transfer interactions and molecular order of rod like mesogens

A mesogenic 4-((4-(alkoxy)phenoxy)carbonyl)phenyl-4-(dimethylamino)benzoate series with terminal chains varying from C2 to C12 carbons (even number carbons only) are synthesised and their mesophase transitions are examined by hot-stage optical polarising microscopy as well as differential scanning calorimetry. Accordingly, enantiotropic nematic mesophase for all the homologs and an additional smectic A phase for the C12 homolog is observed. Powder X-ray diffraction studies confirm the interdigitated bilayer organization in the smectic A phase for the C12 homolog. It is remarkable that the mesogens under investigation only differ in the linking unit i.e. ester versus imine in contrast to recently reported mesogens, yet show a large difference in certain properties. Accordingly, the crystal structure of the C4 homolog reveals a triclinic lattice with P1 space group in which the molecules are packed in a slipped co-facial configuration. Additionally, a detailed investigation of the C12 mesogen by UV-visible and fluorescence spectroscopy as well as computational methods unveils interesting features. The fluorescence spectrum of the C12 mesogen is observed at 366 nm with a shoulder at 433 nm and a large solvent polarity induced red-shift is noticed in contrast to a structurally similar homolog examined recently. Further, the C12 mesogen in solvents such as ethyl acetate, dichloromethane, chloroform, tetrahydrofuran, acetonitrile and dimethyl sulfoxide exhibited dual emission. Therefore, density functional theory and time dependent density functional theory calculations are utilized to obtain insight. Besides variation in the dihedral angle between rings B and C for the C12 mesogen, it is found that the highest occupied molecular orbital (HOMO) is localized on the N,N-dimethylaminobenzene moiety while the lowest unoccupied molecular orbital (LUMO) is mostly concentrated on the phenyl benzoate unit. Time dependent-density functional theory (TD-DFT) calculations disclose the orbitals involved in the dominant excited state electronic transitions and their corresponding energies together with oscillator strength. The high resolution 1D and 2D separated local field (SLF) solid state 13C NMR investigation of the C12 mesogen lead to the orientational order parameters of the phenyl rings of the core in the SmAd phase. The temperature versus alignment induced chemical shifts reveals an increase in chemical shifts with a decrease in temperature in the smectic Ad phase in concurrence with order parameter values. Thus, understanding the photophysical properties of mesogens with dimethylamino moieties would facilitate better design of molecules for application in organic light emitting diodes for polarized emission.

Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity

A series of p-cymene ruthenium dichloro complexes containing isonicotinic ester ligands, [(arene)RuCl2NC5H4-4-COO-C 6H4-p-O-(CH2)n-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7: 4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepared from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal X-ray analysis of 1 shows the molecule to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were observed only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C10 substituent containing a terminal alcohol function, NC 5H4-4-COO-C6H4-p-O-(CH 2)10-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H 4-4-COO-C6H4-p-O-(CH2) 10-OH] (arene = C6H6: 9a, arene = p-MeC 6H4Pri: 9b, arene = C6Me 6: 9c) were prepared. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was observed for complex 9b, with IC50 values of 0.18 μM for A2780 and 3.04 μM for the cisplatin-resistant mutant A2780cisR.

Synthesis and liquid crystal property of new fluoro coumarin carboxylates

New liquid crystalline 4-alkoxyphenyl-coumarin-3-carboxylates 6a-e, 7a-g, 8a-e, and 9a-e were prepared by reacting various coumarin-3-carboxylic acids 5a-d with 4-(alkoxy) phenols 4a-g in the presence of 1(3-dimethylaminopropyl-3- ethylcarbodiimide/dimethyl amino pyridine (EDCI/DMAP) as a coupling agent. The structures of the new coumarin derivatives were confirmed by spectral analysis and the liquid crystalline property was established by polarizing optical microscope and by differential scanning calorimetric techniques. The diethyl amine and morpholine were taken as electron-donating and -CF3 as electron-withdrawing groups at the seventh position of the coumarin-3-carboxylic acids to check the mesomorphic property in all new 4-alkoxyphenyl-coumarin-3- carboxylates. Among them, only 4-alkoxyphenyl-7-triflouromethyl-coumarin-3- carboxylates 7a-g exhibited liquid crystalline SmA phase.