1574-85-2

Usage

Chemical compound

Benzenemethanol, 4-(dimethylamino)-a-ethynyl-

Molecular structure

Consists of a benzene ring attached to a hydroxyl group and an acetylene moiety, as well as a dimethylamino substituent

Common uses

Reagent in organic synthesis, precursor to pharmaceuticals and agrochemicals

Unique properties

Attributed to its structure, valuable building block in creating new chemical compounds

Potential biological and medicinal properties

Subject of interest for drug development and research

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 
• 925-90-6 ethylmagnesium bromide 
• 74-86-2 acetylene 

Downstream Products

• 142354-37-8 1-(4-dimethylaminophenyl)-3-(4-pyridinyl)-2-propyne-1-one 
• 20432-35-3 3-(4-dimethylamino-phenyl)-propenal 
• 132588-83-1 N-(3'-<4''(dimethylamino)phenyl>prop-2'-enylidene)-2,4,6-trimethylaniline 
• 1032426-85-9 [4-(1-allyloxy-prop-2-ynyl)-phenyl]-dimethylamine 

Relevant academic research and scientific papers

N, N-Dimethyl-Substituted Boron Ketoiminates for Multicolor Fluorescent Initiators and Polymers

In this contribution, an efficient synthesis strategy of multicolor fluorescent N,N-dimethyl-substituted boron ketoiminates (NBKI) was presented. The introduction of dimethylamino group as donor and NOBF2 moiety as acceptor with variously tunable substituents led to the formation of D (donor)-π-A (acceptor) system in NBKI molecules, which exhibited a high fluorescence efficiency and a significant red shift of absorption/emission in solution. NBKI molecules were applied in the synthesis of multicolor fluorescent ATRP initiators (i-NBKI 1-4) and RAFT initiator (i-NBKI 5), as well as multicolor fluorescent PS, PMMA, PDBA, or PEG-based homopolymers/copolymers. It was demonstrated that PEG-based polymers showed effective fluorescence emission, good water solubility, and great potential in biological applications. This work bridges the gap in current organoboron compounds and multicolor fluorescent polymerization initiators and related fluorescent polymers/copolymers by utilizing D-π-A design. It may shed light on the downstream applications in next-generation multicolor fluorescent probes/devices.

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Phosphorous acid promoted isomerization of propargyl alcohols to α,β-unsaturated carbonyl compounds

A metal-free and two-phase protocol for the Meyer-Schuster isomerization of propargyl alcohols to the corresponding α,β-unsaturated carbonyl compounds has been achieved in the presence of stoichiometric phosphorous acid aqueous solution, which produces the desired products in high yields with excellent stereoselectivity. Compared with the traditional methods, the procedure features broad scope of the substrates, mild conditions, and easy separation, providing an appealing alternative to the Meyer-Schuster reaction.

Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis

Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.

Parallel synthesis of "Click" chalcones as antitubulin agents

It has been shown that some chalcones are able to inhibit tubulin polymerization, giving cytotoxicity and destruction of tumoral vasculature. A library of 180 novel chalcone analogs has been synthesized via click chemistry and screened for their cytotoxic

4- AND 5-ALKYNYLOXINDOLES AND 4- AND 5-ALKENYLOXINDOLES

4- and 5-alkynyloxindoles as well as 4- and 5-alkenyloxindoles having formula (I) and (II), wherein R, R, R, R, R, X and z have the meaning indicated in the specification, inhibit or modulate protein kinases, in particular JNK protein kinases and are useful as anti-inflammatory agents, particularly in the treatment of rheumatoid arthritis.

1-phenyl-3-aryl-2-propyne-1-one useful as calcium uptake inhibitors

This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.

140. Acid-Catalyzed -Sigmatropic Rearrangements of N-Propargylanilines

The acid-catalyzed rearrangement of N-(1',1'-dimethylprop-2'-ynyl)-, N-(1'-methylprop-2'-ynyl)-, and N-(1'-arylprop-2'-ynyl)-2,6-, 2,4,6-, and 2,3,5,6-, and 2,3,4,5,6-substituted anilines in mixtures of 1N aqueous H2SO4 and ROH such as EtOH, PrOH, BuOH etc., or in CDCl3 or CCl4 in the presence of 4 to 9 mol-equiv. trifluoroacetic acid (TFA) has been investigated (cf.Scheme 12-25 and Tables 6 and 7).The rearrangement of N-(3'-X-1',1'-dimethyl-prop-2'-ynyl)-2,6- and 2,4,6-trimethylanilines (X = Cl, Br, I) in CDCl3/TFA occurs already at 20 deg C with τ1/2 of ca. 1 to 5 h to yield the corresponding 6-(1'-X-3'-methylbuta-1',2'-dienyl)-2,6-dimethyl- or 2,4,6-trimethylcyclohexa-2,4-dien-1-iminium ions (cf.Scheme 13 and Footnotes 26 and 34).When the 4 position is not substituted, a consecutive -sigmatropic rearrangement takes place to yield 2,6-dimethyl-4-(3'-X-1'1'-dimethylprop-2'-ynyl)anilines (cf.Footnotes 26 and 34).A comparable behavior is exhibited by N-(3'chloro-1'-phenylprop-2'-ynyl)-2,6-dimethylaniline (45; cf.Table 7).The acid-catalyzed rearrangement of the anilines with a Cl substituent at C(3') in 1N aqueous H2SO4/ROH at 85-95 deg C, in addition, leads to the formation of 7-chlorotricyclo2,7>oct-3-en-8-ones as the result of an intramolecular Diels-Alder reaction of the primarily formed iminium ions followed by hydrolysis of the iminium function (or vice versa; cf.Schemes 13, 23, and 25 as well as Table 7).When there is no X substituent at C(1') of the iminium-ion intermediate, a -sigmatropic shift of the allenyl moity at C(6) occurs in competition to the -sigmatropic rearrangement to yield the corresponding 3-allenyl-substituted anilines (cf.Schemes 12, 14-18, and 20 as well as Tables 6 and 7).The rearrangement of (-)-(S)-N-(1'phenylprop-2'-ynyl)-2,6-dimethylaniline ((-)-38; cf.Table 7) in a mixture of 1N H2SO4/PrOH at 86 deg C leads to the formation of (-)-(R)-3-(3'-phenylpropa-1',2'-dienyl)-2,6-dimethylaniline ((-)-91), (+)-(E)- and (-)-(Z)-6-benzylidene-1,5-dimethyltricyclo2,7>oct-3-en-8-one ((+)-(E)- and (-)-(Z)-92, respectively), and (-)-(S)-2,6-dimethyl-4-(1'-phenylprop-2'-ynyl)aniline ((-)-93).Recovered starting material (10percent) showed a loss of 18percent of its original optical purity.On the other hand, (+)-(E)- and (-)-(Z)-92 showed the same optical purity as (-)-38, as expected for intramolecular concerted processes.The CD of (+)-(E)- and (-)-(Z)-92 clearly showed that their tricyclic skeletons possess enantiomorphic structures (cf.Fig. 1).Similar results were obtained from the acid-catalyzed rearrangement of (-)-(S)-N-(3'-chloro-1'-phenylprop-2'-ynyl)-2,6-dimethylaniline ((-)-45; cf.Table 7).The recovered starting material exhibited in this case a loss of 48percent of its original optical purity, showing that the Cl substituent favors the heterolytic cleavage of the N-C(1') bond in (-)-45.A still higher degree (78percent) of loss of optical activity of the starting aniline ...