252011-38-4

Upstream product

• 629-05-0 n-octyne 
• 106-37-6 1.4-dibromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 137595-18-7 1-octynylzinc bromide 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 766-96-1 4-bromo-1-ethynylbenzene 

Downstream Products

• 1034330-16-9 5,5-dimethyl-2-(4-(oct-1-yn-1-yl)phenyl)-1,3,2-dioxaborinane 
• 1400773-58-1 1-hexyl-2-(4-(2-thiophenyl)phenyl)acetylene 
• 1400773-60-5 1-hexyl-2-[4-(2-benzo[b]thiophenyl)phenyl]acetylene 
• 1400773-59-2 1-hexyl-2-[4-(2-furanyl)phenyl]acetylene 
• 59662-49-6 4-n-octylbiphenyl-4'-carboxylic acid 
• 1574342-72-5 3-((4-(oct-1-ynyl)phenyl)ethynyl)pyridine 

Relevant academic research and scientific papers

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

A highly efficient and convenient Negishi cross-coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous-flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross-coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional-group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.

SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE

Sphingosine 1-phosphate (S1P) is involved in hyper-proliferative diseases, such as cancer and vascular remodeling in pulmonary arterial hypertension. Inhibitors of sphingosine kinase 1 and 2 (SK1 and SK2), which catalyze the synthesis of S1P, may be useful anti- proliferative agents. We have synthesized a series of sphingosine-based inhibitors of SK and SK2. Also provided in this invention are compounds that activate SK1 which can be used in diseases such as fibrosis, where intracellular S1P is anti-fibrotic.

Structure-Activity relationships and molecular modeling of sphingosine kinase inhibitors

The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases 1 and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of d-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SK1. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.

Synthesis and photoluminescence properties of heterocycle-containing poly(disubstituted acetylene)s

The metathesis polymerizations of disubstituted acetylenes containing heterocycles such as thiophene, furan, benzo[b]thiophene, and benzothiazole were examined using NbCl5, TaCl5, and WCl6. Thiophene-containing monomers polymerized to afford relatively high-molecular-weight polymers in moderate yields. Benzo[b]thiophene-containing monomers also polymerized to give polymers with relatively high molecular weights. On the other hand, furan- and benzothiazole-containing monomers exhibited low metathesis polymerizability, and the polymerizations did not provide high-molecular-weight polymers. Poly(1-hexyl-2-arylacetylene)s having heterocycles [poly(1a) and poly(3a), Scheme 1] emitted blue-colored lights, and the emission maxima were around 480 nm. Heterocycle-containing poly(1-phenyl-2-arylacetylene) [poly(1b)] and poly(1-fluorenyl-2-arylacetylene) [poly(3d)] showed green-colored and yellow-colored emissions, and the emission maxima were 520 and 540 nm, respectively. The emission wavelengths of poly(disubstituted acetylene)s having heterocycles were almost the same as those of the corresponding poly(disubstituted acetylene)s without heterocycles. However, heterocycle-containing polymers showed high fluorescence quantum yields compared to the corresponding polymers without heterocycles. Diarylacetylene polymers showed emission red-shifts between the solution and cast film, while the emission maximum of poly(1-hexyl-2-phenylacetylene) [poly(1a)] in the cast film was almost the same as that in the solution. Benzo[b]thiophene-containing poly(1-(4-trimethylsilylphenyl)-2-phenylacetylene) [poly(3b)] and poly(1-(9,9-dimethyl-2-fluorenyl)-2-phenylacetylene) [poly(3d)] afforded the free-standing membranes because of their high molecular weights. The oxygen permeability coefficient (PO2) of poly(3b) was as large as 1400 barrers. Poly(3d) showed higher gas permeability, and its PO2 was 5300 barrers.

C(sp2)-C(sp) and C(sp)-C(sp) Coupling Reactions Catalyzed by Oxime-Derived Palladacycles

Oxime-derived chloro-bridged palladacycle 8a, derived from 4,4′-dichlorobenzophenone, is an efficient pre-catalyst for the copper- and amine-free Sonogashira coupling between terminal acetylenes and aryl iodides and aryl and vinyl bromides achieving turnover numbers (TON) of up to 72000. Catalyst 8a has also been shown as a effective promoter for the sila-Sonogashira coupling between 1-(trimethylsilyl)alkynes and aryl iodides and bromides in the presence of CuI or Bu4NBr as co-catalysts. This complex also catalyzes efficiently the homocoupling reaction (Glaser-type coupling) between 1-alkynes in NMP at room temperature with TONs of up to 1000. All the reactions can be performed under air and employing reagent-grade chemicals under very low loading conditions, which demonstrates the versatility and high activity of oxime-derived palladacycles.

Acetylene compound, liquid crystal composition and liquid crystal element

Provided are novel acetylene compounds which are useful as a component for a liquid crystal composition used for a liquid crystal element, a liquid crystal composition containing said compounds and a liquid crystal element using said liquid crystal composition. The acetylene compound is represented by Formula (1): n-CmH2m+1—C≡C—A—Z1—B—Y1—R1??(1) wherein m represents an integer of 2 to 24; R1represents a linear or branched alkyl group, a linear or branched alkoxyalkyl group, a linear or branched alkenyl group, or a linear or branched alkenyloxyalkyl group each of which may be substituted with a halogen atom; R1may have an asymmetric carbon atom, and the asymmetric carbon atom may be optically active; A and B represents a cyclic group such as a phenylene group, a biphenylene group, a naphthylene group and the like each of which may be substituted with a halogen atom.